2-Hydroxy-2-(p-tolyl)acetic acid (4-Methylmandelic acid) by Asch

Query Query HO

1. Query

Results

Date

13 substances in Reaxys

2017-06-24 14h:37m:58s (EST)

Search as: As drawn, No mixtures, No charges, No radicals

1/19

2017-06-24 14:38:52

Reaxys ID 2209810 View in Reaxys

1/13 CAS Registry Number: 18584-20-8; 31284-89-6; 58690-84-9; 75172-62-2 Chemical Name: 4-methylmandelic acid Linear Structure Formula: C9H10O3 Molecular Formula: C9H10O3 Molecular Weight: 166.177 Type of Substance: isocyclic InChI Key: SFGURAWGCAPHON-UHFFFAOYSA-N Note:

HO HO O

Substance Label (23) Label References 3b

Merz; Synthesis; (1974); p. 724, View in Reaxys; Moore, Desiree L.; Denton, Allison E.; Kohinke, Rose M.; Craig, Brandon R.; Brenzovich, William E.; Synthetic Communications; vol. 46; nb. 7; (2016); p. 604 612, View in Reaxys

Liu, Xia; Yi, Ze; Wang, Jianhui; Liu, Guiyan; RSC Advances; vol. 5; nb. 14; (2015); p. 10641 - 10646, View in Reaxys

Von Langermann, Jan; Temmel, Erik; Seidel-Morgenstern, Andreas; Lorenz, Heike; Journal of Chemical and Engineering Data; vol. 60; nb. 3; (2015); p. 721 - 728, View in Reaxys

Chen, Lili; Li, Hongji; Yu, Feng; Wang, Lei; Chemical Communications; vol. 50; nb. 94; (2014); p. 14866 14869, View in Reaxys

4CH3C6H4CH(OH )COOH

Shen, Ming-Gui; Shang, Shi-Bin; Song, Zhan-Qian; Wang, Dan; Rao, Xiao-Ping; Gao, Hong; Liu, He; Journal of Chemical Research; vol. 37; nb. 1; (2013); p. 51 - 52, View in Reaxys

Melnicky, Radek; Grepl, Martin; Lycka, Antonin; Bertolasi, Valerio; Kvapil, Lubomir; Dvorakova, Barbora; Hradil, Pavel; Synthesis (Germany); vol. 45; nb. 17; (2013); p. 2447 - 2457; Art.No: SS-2012-Z1009OP, View in Reaxys

rac-1l

Xue, Ya-Ping; Zheng, Yu-Guo; Zhang, Ya-Qin; Sun, Jing-Lei; Liu, Zhi-Qiang; Shen, Yin-Chu; Chemical Communications; vol. 49; nb. 91; (2013); p. 10706 - 10708, View in Reaxys

Curini, Massimo; Epifano, Francesco; Genovese, Salvatore; Marcotullio, M. Carla; Rosati, Ornelio; Organic Letters; vol. 7; nb. 7; (2005); p. 1331 - 1333, View in Reaxys

Boukhris, Said; Souizi, Abdelaziz; Tetrahedron Letters; vol. 41; nb. 15; (2000); p. 2559 - 2562, View in Reaxys

Mizuno, Masanori; Shioiri, Takayuki; Tetrahedron Letters; vol. 39; nb. 50; (1998); p. 9209 - 9210, View in Reaxys

intermed. prod. to 7

Basavaiah, Deevi; Krishna, Peddinti Rama; Tetrahedron; vol. 51; nb. 8; (1995); p. 2403 - 2416, View in Reaxys

Zhou; Yuan; Xie; Synthetic Communications; vol. 24; nb. 1; (1994); p. 43 - 46, View in Reaxys

(+/-)-2

Jeromin, Guenter E.; Albertz, Michael; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 334; nb. 6; (1992); p. 526 - 528, View in Reaxys

Florac; Le Grel; Baudy-Floc'h; Robert; Synthesis; nb. 9; (1991); p. 741 - 743, View in Reaxys

19f

Katritzky, Alan R.; Yang, Zhijun; Lam, Jamshed N.; Synthesis; nb. 8; (1990); p. 666 - 669, View in Reaxys

XIIb

Bal'on, Ya. G.; Smirnov, V. A.; Journal of Organic Chemistry USSR (English Translation); vol. 26; nb. 11; (1990); p. 2051 - 2054; Zhurnal Organicheskoi Khimii; vol. 26; nb. 11; (1990); p. 2377 - 2381, View in Reaxys

XXIII

Bal'on, Ya. G.; Smirnov, V. A.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 12.1; (1989); p. 2249 - 2254; Zhurnal Organicheskoi Khimii; vol. 25; nb. 12; (1989); p. 2507 - 2513, View in Reaxys

8 (R= p-MeC6H4) Legrel, P.; Baudy-Floc'h, M.; Robert, A.; Tetrahedron; vol. 44; nb. 15; (1988); p. 4805 - 4814, View in Reaxys Tab. entry 9. col. 5.

Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Tetrahedron Letters; vol. 28; nb. 24; (1987); p. 2721 - 2722, View in Reaxys

5b=5e

Miura, Masahiro; Akase, Fumiaki; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 52; nb. 12; (1987); p. 2623 - 2625, View in Reaxys

Table 1, Entry 6

Moriarty, Robert M.; Hu, Henry; Tetrahedron Letters; vol. 22; nb. 29; (1981); p. 2747 - 2750, View in Reaxys

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table 1, entry 9, col.2

Reeve, Wilkins; McKee, James R.; Brown, Robert; Lakshmanan, Sitarama; McKee, Gertrude A.; Canadian Journal of Chemistry; vol. 58; (1980); p. 485 - 493, View in Reaxys

269

Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 24; (1963); p. 1,19,97, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Derivative (1) Comment (Derivative) S-Benzyl-isothiuronium-salz; IR, F: 161-162grad

Patent; Bristol-Myers Company; US3985738; (1976); (A1) English, View in Reaxys; Patent; Bristol-Myers Company; US4112228; (1978); (A1) English, View in Reaxys; Patent; Bristol-Myers Company; US4297489; (1981); (A1) English, View in Reaxys References Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 24; (1963); p. 1,19,97, View in Reaxys

Melting Point (16) 1 of 16

Melting Point [°C]

143.74

Solvent (Melting Point)

toluene

Von Langermann, Jan; Temmel, Erik; Seidel-Morgenstern, Andreas; Lorenz, Heike; Journal of Chemical and Engineering Data; vol. 60; nb. 3; (2015); p. 721 - 728, View in Reaxys 2 of 16

Melting Point [°C]

120 - 122

Shen, Ming-Gui; Shang, Shi-Bin; Song, Zhan-Qian; Wang, Dan; Rao, Xiao-Ping; Gao, Hong; Liu, He; Journal of Chemical Research; vol. 37; nb. 1; (2013); p. 51 - 52, View in Reaxys 3 of 16

Melting Point [°C]

120 - 122

Curini, Massimo; Epifano, Francesco; Genovese, Salvatore; Marcotullio, M. Carla; Rosati, Ornelio; Organic Letters; vol. 7; nb. 7; (2005); p. 1331 - 1333, View in Reaxys 4 of 16

Melting Point [°C]

145 - 146

Solvent (Melting Point)

H2O

Claus; Kroseberg; Chemische Berichte; vol. 20; (1887); p. 2051, View in Reaxys; Ando; Nippon Kagaku Kaishi; vol. 56; (1935); p. 745,750; Chem.Abstr.; (1935); p. 7960, View in Reaxys; Bal'on, Ya. G.; Smirnov, V. A.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 12.1; (1989); p. 2249 - 2254; Zhurnal Organicheskoi Khimii; vol. 25; nb. 12; (1989); p. 2507 - 2513, View in Reaxys 5 of 16

Melting Point [°C]

145

Solvent (Melting Point)

toluene

Legrel, P.; Baudy-Floc'h, M.; Robert, A.; Tetrahedron; vol. 44; nb. 15; (1988); p. 4805 - 4814, View in Reaxys 6 of 16

Melting Point [°C]

88 - 89

Moriarty, Robert M.; Hu, Henry; Tetrahedron Letters; vol. 22; nb. 29; (1981); p. 2747 - 2750, View in Reaxys 7 of 16

Melting Point [°C]

145 - 147

Solvent (Melting Point)

benzene

Reeve, Wilkins; McKee, James R.; Brown, Robert; Lakshmanan, Sitarama; McKee, Gertrude A.; Canadian Journal of Chemistry; vol. 58; (1980); p. 485 - 493, View in Reaxys 8 of 16

Melting Point [°C]

145 - 146

v. Auwers; Chemische Berichte; vol. 49; (1916); p. 2400, View in Reaxys; Klingenberg et al.; Journal of Chemical and Engineering Data; vol. 23; (1978); p. 327,328, View in Reaxys 9 of 16

Melting Point [°C]

144

Merz; Synthesis; (1974); p. 724, View in Reaxys 10 of 16

Melting Point [°C]

144.5 - 145.5

Freeman; Scott; Journal of Organic Chemistry; vol. 35; (1970); p. 2989,2990, View in Reaxys 11 of 16

Melting Point [°C]

145

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Grundy,M.E. et al.; Journal of the Chemical Society; (1960); p. 372 - 376, View in Reaxys 12 of 16

Melting Point [°C]

144

Solvent (Melting Point)

H2O

Kindler; Metzendorf; Kwok; Chemische Berichte; vol. 76; (1943); p. 308,314, View in Reaxys 13 of 16

Melting Point [°C]

144

Solvent (Melting Point)

benzene

Kindler; Metzendorf; Kwok; Chemische Berichte; vol. 76; (1943); p. 308,314, View in Reaxys 14 of 16

Melting Point [°C]

145 - 145.5

Riebsomer; Irvine; Andrews; Journal of the American Chemical Society; vol. 60; (1938); p. 1015, View in Reaxys 15 of 16

Melting Point [°C]

145

Solvent (Melting Point)

benzene

Riebsomer et al.; Journal of the American Chemical Society; vol. 60; (1938); p. 2975; Journal of the American Chemical Society; vol. 64; (1942); p. 2080, View in Reaxys 16 of 16

Melting Point [°C]

144 - 145

Tiffeneau; Levy; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1738,1746, View in Reaxys Association (MCS) (19) 1 of 19

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

aq. acetic acid

Temperature (Association (MCS)) [°C]

14.85 - 29.85

Partner (Association (MCS))

bis(2,2'-bipyridyl)copper(II) permangamate

Satsangi, Baljeet Kaur; Kothari, Seema; Journal of the Indian Chemical Society; vol. 74; nb. 1; (1997); p. 16 - 20, View in Reaxys 2 of 19

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CHCl3

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Asopa, Rachna; Bhatt, Pallavi; Banerji, Kalyan K; Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry; vol. 31; nb. 9; (1992); p. 706 - 709, View in Reaxys 3 of 19

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CS2

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

1,2-dichloro-ethane

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Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

dimethylsulfoxide

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CH2Cl2

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

acetone

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

dimethylformamide

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

butan-2-one

Temperature (Association (MCS)) [°C]

14.9 - 44.9

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Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

nitrobenzene

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

benzene

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

cyclohexane

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

toluene

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

2-methyl-propan-2-ol

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

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Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

dioxane

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

1,2-dimethoxy-ethane

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

acetic acid

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

ethyl acetate

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

tetrahydrofuran

Temperature (Association (MCS)) [°C]

14.9 - 44.9

Partner (Association (MCS))

pyridinium fluorochromate

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Object of Investigation

References

Conformation

Mori et al.; Bulletin of the Chemical Society of Japan; vol. 42; (1969); p. 488, View in Reaxys

Crystal Property Description (3) Colour & Other Location Properties colourless

supporting information

References Moore, Desiree L.; Denton, Allison E.; Kohinke, Rose M.; Craig, Brandon R.; Brenzovich, William E.; Synthetic Communications; vol. 46; nb. 7; (2016); p. 604 - 612, View in Reaxys

yellow

Curini, Massimo; Epifano, Francesco; Genovese, Salvatore; Marcotullio, M. Carla; Rosati, Ornelio; Organic Letters; vol. 7; nb. 7; (2005); p. 1331 - 1333, View in Reaxys

Tafeln

Claus; Kroseberg; Chemische Berichte; vol. 20; (1887); p. 2051, View in Reaxys

Dissociation Exponent (1) 1 of 1

Comment (Dissociation Exponent)

(pk')pKa

Klingenberg et al.; Journal of Chemical and Engineering Data; vol. 23; (1978); p. 327,328, View in Reaxys Enthalpy of Fusion (1) Enthalpy of FuComment (Ension [Jmol-1] thalpy of Fusion) 25600

416.9 K

References Von Langermann, Jan; Temmel, Erik; Seidel-Morgenstern, Andreas; Lorenz, Heike; Journal of Chemical and Engineering Data; vol. 60; nb. 3; (2015); p. 721 - 728, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 24; (1963); p. 1,19,97, View in Reaxys

NMR Spectroscopy (8) 1 of 8

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Moore, Desiree L.; Denton, Allison E.; Kohinke, Rose M.; Craig, Brandon R.; Brenzovich, William E.; Synthetic Communications; vol. 46; nb. 7; (2016); p. 604 - 612, View in Reaxys 2 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy) [MHz]

200

Curini, Massimo; Epifano, Francesco; Genovese, Salvatore; Marcotullio, M. Carla; Rosati, Ornelio; Organic Letters; vol. 7; nb. 7; (2005); p. 1331 - 1333, View in Reaxys 3 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Frequency (NMR Spectroscopy) [MHz]

50.32

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Curini, Massimo; Epifano, Francesco; Genovese, Salvatore; Marcotullio, M. Carla; Rosati, Ornelio; Organic Letters; vol. 7; nb. 7; (2005); p. 1331 - 1333, View in Reaxys 4 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3; trifluoroacetic acid scopy) Frequency (NMR Spectroscopy) [MHz]

250

Boukhris, Said; Souizi, Abdelaziz; Tetrahedron Letters; vol. 41; nb. 15; (2000); p. 2559 - 2562, View in Reaxys 5 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- acetone-d6 scopy) Florac; Le Grel; Baudy-Floc'h; Robert; Synthesis; nb. 9; (1991); p. 741 - 743, View in Reaxys 6 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3; trifluoroacetic acid scopy) Legrel, P.; Baudy-Floc'h, M.; Robert, A.; Tetrahedron; vol. 44; nb. 15; (1988); p. 4805 - 4814, View in Reaxys 7 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Reeve, Wilkins; McKee, James R.; Brown, Robert; Lakshmanan, Sitarama; McKee, Gertrude A.; Canadian Journal of Chemistry; vol. 58; (1980); p. 485 - 493, View in Reaxys 8 of 8

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-1H

Reeve, Wilkins; McKee, James R.; Brown, Robert; Lakshmanan, Sitarama; McKee, Gertrude A.; Canadian Journal of Chemistry; vol. 58; (1980); p. 485 - 493, View in Reaxys IR Spectroscopy (6) 1 of 6

Description (IR Spectroscopy)

ATR (attenuated total reflectance); Bands

Location

supporting information

Moore, Desiree L.; Denton, Allison E.; Kohinke, Rose M.; Craig, Brandon R.; Brenzovich, William E.; Synthetic Communications; vol. 46; nb. 7; (2016); p. 604 - 612, View in Reaxys 2 of 6

Description (IR Spectroscopy)

Bands

Curini, Massimo; Epifano, Francesco; Genovese, Salvatore; Marcotullio, M. Carla; Rosati, Ornelio; Organic Letters; vol. 7; nb. 7; (2005); p. 1331 - 1333, View in Reaxys

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3 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Boukhris, Said; Souizi, Abdelaziz; Tetrahedron Letters; vol. 41; nb. 15; (2000); p. 2559 - 2562, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

3407 - 1710 cm**(-1)

Legrel, P.; Baudy-Floc'h, M.; Robert, A.; Tetrahedron; vol. 44; nb. 15; (1988); p. 4805 - 4814, View in Reaxys; Florac; Le Grel; Baudy-Floc'h; Robert; Synthesis; nb. 9; (1991); p. 741 - 743, View in Reaxys 5 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3450 - 580 cm**(-1)

Reeve, Wilkins; McKee, James R.; Brown, Robert; Lakshmanan, Sitarama; McKee, Gertrude A.; Canadian Journal of Chemistry; vol. 58; (1980); p. 485 - 493, View in Reaxys 6 of 6

Description (IR Spectroscopy)

Spectrum

Mori et al.; Bulletin of the Chemical Society of Japan; vol. 42; (1969); p. 488, View in Reaxys

Reaxys ID 2576209 View in Reaxys

2/13 CAS Registry Number: 18584-20-8; 31284-89-6; 58690-84-9; 75172-62-2 Chemical Name: (S)-2-hydroxy-2-(p-tolyl)acetic acid; (S)-4methylmandelic acid; (S)-p-methylmandelic acid; (S)-p-methylmandelic acid; p-Methyl-phenylglyoxylsaeure Linear Structure Formula: C9H10O3 Molecular Formula: C9H10O3 Molecular Weight: 166.177 Type of Substance: isocyclic InChI Key: SFGURAWGCAPHON-QMMMGPOBSA-N Note:

OH H HO

Substance Label (4) Label References 3j

Yan, Pu-Cha; Xie, Jian-Hua; Zhang, Xiang-Dong; Chen, Kang; Li, Yuan-Qiang; Zhou, Qi-Lin; Che, DaQing; Chemical Communications; vol. 50; nb. 100; (2014); p. 15987 - 15990, View in Reaxys; Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; Yan, Pucha; Che, Daqing; Lin, Yuanqiang; Zhang, Xiangdong; Chen, Kang; Yan, Yongliang; (12 pag.); CN105481677; (2016); (A) Chinese, View in Reaxys

Von Langermann, Jan; Temmel, Erik; Seidel-Morgenstern, Andreas; Lorenz, Heike; Journal of Chemical and Engineering Data; vol. 60; nb. 3; (2015); p. 721 - 728, View in Reaxys

(S)-1b

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys

3, R=4-CH3

Effenberger, Franz; Hoersch, Brigitte; Foerster, Siegfried; Ziegler, Thomas; Tetrahedron Letters; vol. 31; nb. 9; (1990); p. 1249 - 1252, View in Reaxys

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound

10/19

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Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; Yan, Pucha; Che, Daqing; Lin, Yuanqiang; Zhang, Xiangdong; Chen, Kang; Yan, Yongliang; (12 pag.); CN105481677; (2016); (A) Chinese, View in Reaxys prophetic product

Sheet 35

Derivative (1) Comment (Derivative)

References

Patent; BASF Enzymes LLC; Chaplin, Jennifer A.; Chi, Ellen; DeSantis, Grace; Madden, Mark; Milan, Aileen; Robertson, Dan E.; Short, Jay M.; Weiner, David P.; US9217164; (2015); (B2) English, View in Reaxys

By formation of Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; salt/complex with (1991); p. 2322 - 2326, View in Reaxys (-)-α-phenylethylamine. Melting point at: 189 C 200 C. Additional data: <α>28 D = 47 (c 1.25, CH3OH) Purification (1) Purification (method) fractional recrystallization of the (-)-α-phenylethylamine salts from methanol

References Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

131.44

Solvent (Melting Point)

toluene

Von Langermann, Jan; Temmel, Erik; Seidel-Morgenstern, Andreas; Lorenz, Heike; Journal of Chemical and Engineering Data; vol. 60; nb. 3; (2015); p. 721 - 728, View in Reaxys 2 of 3

Melting Point [°C]

128 - 132

Solvent (Melting Point)

toluene

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys 3 of 3

Melting Point [°C]

100

Rindt et al.; Tetrahedron; vol. 29; (1973); p. 3051, View in Reaxys Circular Dichroism (1) Solvent (Circular Comment (CircuDichroism) lar Dichroism) methanol

278 - 222 nm

Crystal Property Description (1) Colour & Other Location Properties white

supporting information

Enthalpy of Fusion (1) Enthalpy of FuComment (Ension [Jmol-1] thalpy of Fusion) 22400

404.6 K

Liquid Phase (1) Description (Liquid Phase)

References

References Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys References Yan, Pu-Cha; Xie, Jian-Hua; Zhang, Xiang-Dong; Chen, Kang; Li, Yuan-Qiang; Zhou, Qi-Lin; Che, Da-Qing; Chemical Communications; vol. 50; nb. 100; (2014); p. 15987 - 15990, View in Reaxys References Von Langermann, Jan; Temmel, Erik; Seidel-Morgenstern, Andreas; Lorenz, Heike; Journal of Chemical and Engineering Data; vol. 60; nb. 3; (2015); p. 721 - 728, View in Reaxys

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Self-association in solution

Rindt et al.; Tetrahedron; vol. 29; (1973); p. 3051, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.09 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

145

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Yan, Pu-Cha; Xie, Jian-Hua; Zhang, Xiang-Dong; Chen, Kang; Li, Yuan-Qiang; Zhou, Qi-Lin; Che, Da-Qing; Chemical Communications; vol. 50; nb. 100; (2014); p. 15987 - 15990, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Location

supporting information

Yan, Pu-Cha; Xie, Jian-Hua; Zhang, Xiang-Dong; Chen, Kang; Li, Yuan-Qiang; Zhou, Qi-Lin; Che, Da-Qing; Chemical Communications; vol. 50; nb. 100; (2014); p. 15987 - 15990, View in Reaxys UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 252; 220 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

170; 6900

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys

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2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 273; 268; 264; 257 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

160; 180; 250; 190

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys

Reaxys ID 3198865 View in Reaxys

3/13 CAS Registry Number: 18584-20-8; 58690-84-9; 75172-62-2; 31284-89-6 Chemical Name: (R)-4-methylmandelic acid; (R)-p-methylmandelic acid; R-4-methylmandelic acid; 4-methyl-D-mandelic acid; 4-Methyl-D-mandelsaeure; (R)-(-)-4-methylmandelic acid; (R)p-methyl-mandelic acid Linear Structure Formula: C9H10O3 Molecular Formula: C9H10O3 Molecular Weight: 166.177 Type of Substance: isocyclic InChI Key: SFGURAWGCAPHON-MRVPVSSYSA-N Note:

Substance Label (5) Label References (R)-1l

Xue, Ya-Ping; Zheng, Yu-Guo; Zhang, Ya-Qin; Sun, Jing-Lei; Liu, Zhi-Qiang; Shen, Yin-Chu; Chemical Communications; vol. 49; nb. 91; (2013); p. 10706 - 10708, View in Reaxys

(R)-1b

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys

(R)-1e

Effenberger, Franz; Hopf, Martin; Ziegler, Thomas; Hudelmayer, Jochen; Chemische Berichte; vol. 124; (1991); p. 1651 - 1659, View in Reaxys

(R)-3c

Ziegler, Thomas; Hoersch, Brigitte; Effenberger, Franz; Synthesis; nb. 7; (1990); p. 575 - 578, View in Reaxys

Tab.I

Hoover; Dunn; Jakas; Lam; Taggart; Guarini; Phillips; Journal of Medicinal Chemistry; vol. 17; nb. 1; (1974); p. 34 - 41, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Sheet 35

Derivative (1) Comment (Derivative)

References

cinchonine salt Fujise; Iwakiri; Biochemische Zeitschrift; vol. 283; (1936); p. 298, View in Reaxys (mp: 145 degree ; <alpha>=76.2 degree ); Further Data see Handbook Purification (1) Purification (method)

References

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(+)-α-methylbenzylamine

Hoover; Dunn; Jakas; Lam; Taggart; Guarini; Phillips; Journal of Medicinal Chemistry; vol. 17; nb. 1; (1974); p. 34 - 41, View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

132 - 134

Hoover; Dunn; Jakas; Lam; Taggart; Guarini; Phillips; Journal of Medicinal Chemistry; vol. 17; nb. 1; (1974); p. 34 - 41, View in Reaxys 2 of 3

Melting Point [°C]

131

Solvent (Melting Point)

H2O

Veibel; Hansen; Enzymol.; vol. 9; (1940); p. 180,183, View in Reaxys 3 of 3

Melting Point [°C]

131

Solvent (Melting Point)

benzene

Fujise; Iwakiri; Biochemische Zeitschrift; vol. 283; (1936); p. 298, View in Reaxys Optical Rotatory Power (4) 1 of 4

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.34 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-135.3

Wavelength (Optical Ro- 578 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Ziegler, Thomas; Hoersch, Brigitte; Effenberger, Franz; Synthesis; nb. 7; (1990); p. 575 - 578, View in Reaxys 2 of 4

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.3 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-153

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Hoover; Dunn; Jakas; Lam; Taggart; Guarini; Phillips; Journal of Medicinal Chemistry; vol. 17; nb. 1; (1974); p. 34 - 41, View in Reaxys 3 of 4

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-148.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Veibel; Hansen; Enzymol.; vol. 9; (1940); p. 180,183, View in Reaxys

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4 of 4

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-148

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Fujise; Iwakiri; Biochemische Zeitschrift; vol. 283; (1936); p. 298, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- acetone-d6 scopy) Ziegler, Thomas; Hoersch, Brigitte; Effenberger, Franz; Synthesis; nb. 7; (1990); p. 575 - 578, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1705 cm**(-1)

Ziegler, Thomas; Hoersch, Brigitte; Effenberger, Franz; Synthesis; nb. 7; (1990); p. 575 - 578, View in Reaxys

Reaxys ID 5477748 View in Reaxys

4/13 CAS Registry Number: 18584-20-8; 31284-89-6; 58690-84-9; 75172-62-2 Chemical Name: (-)-p-methylmandelic acid Linear Structure Formula: C9H10O3 Molecular Formula: C9H10O3 Molecular Weight: 166.177 Type of Substance: isocyclic InChI Key: SFGURAWGCAPHON-UHFFFAOYSA-N Note:

HO HO O (-)-enantiomer

Substance Label (1) Label References (-)-2 Purification (1) Purification (method)

Jeromin, Guenter E.; Albertz, Michael; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 334; nb. 6; (1992); p. 526 - 528, View in Reaxys References

separation of Jeromin, Guenter E.; Albertz, Michael; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 334; nb. 6; racemat via reac- (1992); p. 526 - 528, View in Reaxys tion with vinyl acetate in the presence of Pseudomonas sp. lipase Optical Rotatory Power (1)

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1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.5 g/100ml

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-147

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Jeromin, Guenter E.; Albertz, Michael; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 334; nb. 6; (1992); p. 526 - 528, View in Reaxys

Reaxys ID 22900784 View in Reaxys

5/13 Linear Structure Formula: C9H10O3 Molecular Formula: C9H10O3 Molecular Weight: 166.177 InChI Key: SFGURAWGCAPHON-QMMMGPOBSA-N Note:

OH HO O rel-configuration

Reaxys ID 21156481 View in Reaxys

6/13 Linear Structure Formula: C9H9 (2)HO3 Molecular Formula: C9H10O3 Molecular Weight: 167.169 InChI Key: SFGURAWGCAPHON-BNEYPBHNSA-N Note:

OH OH 2H

Reaxys ID 2989288 View in Reaxys 2H

7/13 Chemical Name: p-Methylperdeuteromandelsaeure Linear Structure Formula: C9H3D7O3 Molecular Formula: C9H10O3 Molecular Weight: 173.121 Type of Substance: isocyclic InChI Key: SFGURAWGCAPHON-AAYPNNLASA-N Note:

2H 2

2H 2H

HO O 2H

Melting Point (1) 1 of 1

Melting Point [°C]

144 - 146

Karafiloglou et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1977); p. 1545,1546,1547, View in Reaxys

Reaxys ID 4771899 View in Reaxys

8/13

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CAS Registry Number: 132699-02-6 Chemical Name: (S)-p-methylmandelic acid potassium salt Linear Structure Formula: C9H9O3 (1-)*K(1+) Molecular Formula: C9H9O3*K Molecular Weight: 204.267 Type of Substance: isocyclic InChI Key: AVFGYIOETVIAQZ-QRPNPIFTSA-M Note:

K+ HO O O–

Substance Label (1) Label References (S)-3b

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys

Circular Dichroism (1) Solvent (Circular Comment (CircuDichroism) lar Dichroism)

References

methanol; aq. KOH

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys

280 - 239 nm

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol; aq. KOH

Absorption Maxima (UV/ 273; 265; 259; 222 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

240; 300; 240; 8100

Colon, Diana F.; Pickard, Simeon T.; Smith, Howard E.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2322 - 2326, View in Reaxys

Reaxys ID 27994950 View in Reaxys

9/13 Chemical Name: pyiridine R-4-methylmandelic acid Linear Structure Formula: C9H10O3*C5H5N Molecular Formula: C5H5N*C9H10O3 Molecular Weight: 245.278 InChI Key: BLZUTAFIWZUXKM-DDWIOCJRSA-N Note:

OH OH N O

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Buchard, Antoine; Carbery, David R.; Davidson, Matthew G.; Ivanova, Petya K.; Jeffery, Ben J.; Kociok-Köhn, Gabriele I.; Lowe, John P.; Angewandte Chemie - International Edition; vol. 53; nb. 50; (2014); p. 13858 - 13861; Angew. Chem.; vol. 126; nb. 50; (2014); p. 14078 - 14081,4, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Reaxys ID 3752036 View in Reaxys O

O–

10/13 Linear Structure Formula: Ag(1+)*OCOCH(OH)C6H4CH3 (1-)=AgCO CH(OH)C H CH 2 6 4 3 Molecular Formula: Ag*C9H9O3 Molecular Weight: 273.037 Type of Substance: isocyclic InChI Key: LAQXUNOURXYJTL-UHFFFAOYSA-M Note:

Ag+

Reaxys ID 9085037 View in Reaxys

11/13 Linear Structure Formula: C9H10O3*C8H11N Molecular Formula: C8H11N*C9H10O3 Molecular Weight: 287.359 Type of Substance: isocyclic InChI Key: JPIGDCRVTCSTQL-UHFFFAOYSA-N Note:

H 2N HO HO O

Substance Label (1) Label References 2*6

Kinbara, Kazushi; Tagawa, Yoshiyuki; Saigo, Kazuhiko; Tetrahedron Asymmetry; vol. 12; nb. 21; (2001); p. 2927 - 2930, View in Reaxys

Crystal Phase (1) Description (Crys- References tal Phase) Crystal structure determination

Kinbara, Kazushi; Tagawa, Yoshiyuki; Saigo, Kazuhiko; Tetrahedron Asymmetry; vol. 12; nb. 21; (2001); p. 2927 - 2930, View in Reaxys

Crystal System (1) Crystal System References rhombic Space Group (1) Space Group 19

Kinbara, Kazushi; Tagawa, Yoshiyuki; Saigo, Kazuhiko; Tetrahedron Asymmetry; vol. 12; nb. 21; (2001); p. 2927 - 2930, View in Reaxys References Kinbara, Kazushi; Tagawa, Yoshiyuki; Saigo, Kazuhiko; Tetrahedron Asymmetry; vol. 12; nb. 21; (2001); p. 2927 - 2930, View in Reaxys

Reaxys ID 3811970 View in Reaxys

12/13

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CAS Registry Number: 93731-99-8 Chemical Name: 4-methyl-mandelic acid; S-benzyl-thiuroniumsalt; 4-Methyl-mandelsaeure; S-Benzyl-thiouronium-Salz Linear Structure Formula: C9H10O3*C8H10N2S Molecular Formula: C8H10N2S*C9H10O3 Molecular Weight: 332.423 Type of Substance: isocyclic InChI Key: DVBWWQIXBHOQON-UHFFFAOYSA-N Note:

HN S H 2N HO HO O

Melting Point (1) 1 of 1

Melting Point [°C]

164 - 165

Solvent (Melting Point)

ethanol

Friediger; Pedersen; Acta Chemica Scandinavica (1947-1973); vol. 9; (1955); p. 1425,1428, View in Reaxys

Reaxys ID 15650806 View in Reaxys

13/13

Chemical Name: tert-butyl rac-(SR,SR)-2-aminocyclopentylcarbamate (R)-(-)-4-methylmandelate Linear Structure Formula: C9H10O3*C10H20N2O2 Molecular Formula: C9H10O3*C10H20N2O2 Molecular Weight: 366.458 InChI Key: OXUWQRMUSSUEMK-BCGLFXBXSA-N Note:

HO O O O HN H 2N racemate

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