3-oxo-2-phenylbutanenitrile

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2016-08-08 00h:27m:45s (EST)

N

1. Query O

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

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Reaxys ID 743161 View in Reaxys

1/2 CAS Registry Number: 4468-48-8 Chemical Name: 1-phenyl-1-cyanopropan-2-one Linear Structure Formula: CH3COCH(C6H5)CN Molecular Formula: C10H9NO Molecular Weight: 159.188 Type of Substance: isocyclic InChI Key: KHNWFTMUBKJWRZ-UHFFFAOYSA-N Note:

N

O

Substance Label (22) Label References 3a

Bobylev; Kobrakov; Kuznetsov; Ruchkina; Fakhrutdinov; Russian Journal of Organic Chemistry; vol. 51; nb. 11; (2015); p. 1572 - 1577; Zh. Org. Khim.; vol. 51; nb. 11; (2015); p. 1603 - 1608,6, View in Reaxys

9g

Kim, Bo Ram; Lee, Hyung-Geun; Kang, Seung-Beom; Jung, Kwang-Ju; Sung, Gi Hyeon; Kim, JeumJong; Lee, Sang-Gyeong; Yoon, Yong-Jin; Tetrahedron; vol. 69; nb. 48; (2013); p. 10331 - 10336, View in Reaxys

3

Jonczyk, Andrzej; Gierczak, Agnieszka H; Tetrahedron; vol. 56; nb. 33; (2000); p. 6083 - 6087, View in Reaxys; Rodriguez, Cristina; de Gonzalo, Gonzalo; Torres Pazmino, Daniel E.; Fraaije, Marco W.; Gotor, Vicente; Tetrahedron Asymmetry; vol. 19; nb. 2; (2008); p. 197 - 203, View in Reaxys

starting to 2g

Chiba, Shunsuke; Hattori, Gaku; Narasaka, Koichi; Chemistry Letters; vol. 36; nb. 1; (2007); p. 52 - 53, View in Reaxys

2b

Aggarwal, Ranjana; Kumar, Vinod; Tyagi, Parikshit; Singh, Shiv P.; Bioorganic and Medicinal Chemistry; vol. 14; nb. 6; (2006); p. 1785 - 1791, View in Reaxys

10d

Kamila, Sukanta; Koh, Benjamin; Biehl, Edward R.; Synthetic Communications; vol. 36; nb. 23; (2006); p. 3493 - 3507, View in Reaxys

I-161

Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); (A1) English, View in Reaxys

26

Pavlik, James W.; St. Martin, Heather; Lambert, Karen A.; Lowell, Jennifer A.; Tsefrikas, Vikki M.; Eddins, Cheryl K.; Kebede, Naod; Journal of Heterocyclic Chemistry; vol. 42; nb. 2; (2005); p. 273 - 281, View in Reaxys

2, R'=Me

Yavari, Issa; Islami, Mohammad R.; Habibi, Azizollah; Tikdari, Ahmad M.; Ebrahimi, Lona; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 3; (2004); p. 575 - 583, View in Reaxys

10, X=H

Chen, Chen; Wilcoxen, Keith M.; Huang, Charles Q.; McCarthy, James R.; Chen, Takung; Grigoriadis, Dimitri E.; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 14; (2004); p. 3669 - 3673, View in Reaxys

1s

Gotor, Vicente; Liz, Ramon; Testera, Ana Ma; Tetrahedron; vol. 60; nb. 3; (2004); p. 607 - 618, View in Reaxys

13c

Dastrup, David M.; Yap, Amy H.; Weinreb, Steven M.; Henry, James R.; Lechleiter, Andrew J.; Tetrahedron; vol. 60; nb. 4; (2004); p. 901 - 906, View in Reaxys

educt to 9/10

Attanasi, Orazio A.; Filippone, Paolino; Perrulli, Francesca R.; Santeusanio, Stefania; European Journal of Organic Chemistry; nb. 14; (2002); p. 2323 - 2330, View in Reaxys

1e

De Nino, Antonio; Dalpozzo, Renato; Cupone, Giovanna; Maiuolo, Loredana; Procopio, Antonio; Tagarelli, Antonio; Bartoli, Giuseppe; European Journal of Organic Chemistry; nb. 17; (2002); p. 2924 - 2927, View in Reaxys

1a

Dalpozzo, Renato; Bartoli, Giuseppe; Bosco, Marcella; De Nino, Antonio; Procopio, Antonio; Sambri, Letizia; Tagarelli, Antonio; European Journal of Organic Chemistry; nb. 15; (2001); p. 2971 - 2976, View in Reaxys

6

Glushkov; Karmanov; Feshina; Postanogova; Shklyaev; Chemistry of Heterocyclic Compounds; vol. 37; nb. 1; (2001); p. 103 - 108, View in Reaxys

IV

Gololobov; Galkina; Dovgan'; Krasnova; Petrovskii; Schmutzler; Karasar; Freitag; Jones; Russian Journal of Organic Chemistry; vol. 37; nb. 8; (2001); p. 1061 - 1067, View in Reaxys

ketone for 19

Chen, Ning; Lu, Yuelie; Gadamasetti, Kumar; Hurt, Clarence R.; Norman, Mark H.; Fotsch, Christopher; Journal of Organic Chemistry; vol. 65; nb. 8; (2000); p. 2603 - 2605, View in Reaxys

t.1,edd.,entry 6

Redman; Dumas; Scott; Organic letters; vol. 2; nb. 14; (2000); p. 2061 - 2063, View in Reaxys

4

Vedernikova, Irina V.; Haemers, Achiel; Ryabukhin, Yuryi I.; Journal of Heterocyclic Chemistry; vol. 36; nb. 1; (1999); p. 97 - 104, View in Reaxys

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Id

Emelina; Petrov; Russian Journal of Organic Chemistry; vol. 35; nb. 1; (1999); p. 119 - 123, View in Reaxys

6a

Attanasi, Orazio A.; Filippone, Paolino; Guidi, Barbara; Perrulli, Francesca R.; Santeusanio, Stefania; Heterocycles; vol. 51; nb. 10; (1999); p. 2423 - 2430, View in Reaxys

Patent-Specific Data (2) References Patent; Bold, Guido; Floersheimer, Andreas; Furet, Pascal; Imbach, Patricia; Masuya, Keiichi; Schoepfer, Joseph G.; US2005/222171; (2005); (A1) English, View in Reaxys Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70431; (2005); (A1) English, View in Reaxys Related Structure (2) Related Structure Referenced Com- References pound The following tau- α-acetylphenylatomers are discetonitrile cussed: /BRN= 4969228/

Kern, J. M.; Sauer, J. D.; Federlin, P.; Tetrahedron; vol. 38; nb. 20; (1982); p. 3023 3033, View in Reaxys

Malawski; Czerska; Roczniki Chemii; vol. 34; (1960); p. 491,495; Chem.Abstr.; nb. 23632f; (1960), View in Reaxys Derivative (4) Comment (Derivative) K-Enolat:E(1/2 ox.)

References Kern; Federlin; Tetrahedron; vol. 34; (1978); p. 661,663, View in Reaxys

Na-Salz: Rk. mit Ravoux,J.-P.; Decombe,J.; Bulletin de la Societe Chimique de France; (1969); p. 146 - 153, View in Reaxys N.N-Dimethylaminomethylferrocen-methojodid > 3-Ferrocenyl-2phenyl-propionitril Guanylhydrazonsulfat (C11H13N5)2*H2 SO4*2H2O: F.: 183-185grad (Zers.) (Tab.I)

Somasekhara et al.; Current Science; vol. 37; (1968); p. 669, View in Reaxys

phenylhydrazone Heller; Journal fuer Praktische Chemie (Leipzig); vol. <2> 120; (1929); p. 196, View in Reaxys (mp: 114 degree ) Melting Point (23) 1 of 23

Melting Point [°C]

75 - 77

Kim, Bo Ram; Lee, Hyung-Geun; Kang, Seung-Beom; Jung, Kwang-Ju; Sung, Gi Hyeon; Kim, Jeum-Jong; Lee, Sang-Gyeong; Yoon, Yong-Jin; Tetrahedron; vol. 69; nb. 48; (2013); p. 10331 - 10336, View in Reaxys 2 of 23

Melting Point [°C]

215

Patent; Bold, Guido; Floersheimer, Andreas; Furet, Pascal; Imbach, Patricia; Masuya, Keiichi; Schoepfer, Joseph G.; US2005/222171; (2005); (A1) English, View in Reaxys; Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70431; (2005); (A1) English, View in Reaxys; Patent; Sivasankaran, Rajeev; Zimmermann, Kaspar; US2009/69315; (2009); (A1) English, View in Reaxys 3 of 23

Melting Point [°C]

78 - 79

Kamila, Sukanta; Koh, Benjamin; Biehl, Edward R.; Synthetic Communications; vol. 36; nb. 23; (2006); p. 3493 3507, View in Reaxys 4 of 23

Melting Point [°C]

97

Solvent (Melting Point)

ethyl acetate; hexane

Itoh; Fukuda; Fujisawa; Bulletin of the Chemical Society of Japan; vol. 62; nb. 12; (1989); p. 3851 - 3855, View in Reaxys 5 of 23

Melting Point [°C]

92

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Bellec et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 281; (1975); p. 885, View in Reaxys; Bellec et al.; Journal of Heterocyclic Chemistry; vol. 16; (1979); p. 1611,1615, View in Reaxys 6 of 23

Melting Point [°C]

88.5 - 89.5

Miyano; Abe; Journal of Organic Chemistry; vol. 36; (1971); p. 2948, View in Reaxys 7 of 23

Melting Point [°C]

86 - 90

Patent; Tecnifax Corp.; US3558318; (1971); Chem.Abstr.; vol. 74; nb. 88683, View in Reaxys 8 of 23

Melting Point [°C]

88 - 89.5

De Jongh et al.; Journal of Organic Chemistry; vol. 36; (1971); p. 3160,3167, View in Reaxys 9 of 23

Melting Point [°C]

82

Biniecki; Herold; Acta poloniae pharmaceutica; vol. 27; nb. 6; (1970); p. 529 - 532, View in Reaxys; Ogata et al.; Tetrahedron; vol. 24; (1968); p. 1617,1620, View in Reaxys 10 of 23

Melting Point [°C]

85 - 86

Somasekhara et al.; Current Science; vol. 37; (1968); p. 669, View in Reaxys 11 of 23

Melting Point [°C]

88 - 89

Patent; Bristol-Banyu Res.Inst.; US3360527; (1966); Chem.Abstr.; vol. 69; nb. 36117g; (1968), View in Reaxys 12 of 23

Melting Point [°C]

88.5 - 89.5

Solvent (Melting Point)

aq. methanol

Kimball; Journal of the American Chemical Society; vol. 58; (1963); p. 1963,1968, View in Reaxys 13 of 23

Melting Point [°C]

87 - 88

Solvent (Melting Point)

petroleum ether

Furukawa,M. et al.; Chemical and Pharmaceutical Bulletin; vol. 9; (1961); p. 914 - 921, View in Reaxys 14 of 23

Melting Point [°C]

89

Normant; Angelo; Bulletin de la Societe Chimique de France; (1960); p. 357, View in Reaxys 15 of 23

Melting Point [°C]

86 - 88

Rossi et al.; Helvetica Chimica Acta; vol. 43; (1960); p. 1046,1052, View in Reaxys 16 of 23

Melting Point [°C]

90

Solvent (Melting Point)

ethanol

Mueller; Gawlick; Kreutzmann; Justus Liebigs Annalen der Chemie; vol. 515; (1935); p. 100,109, View in Reaxys; Arndt; Loewe; Ginkoek; Istanbul Universitesi Fen Fakultesi Mecmuasi; vol. <A> 11; (1946); p. 150,159; Chem.Abstr.; (1947); p. 3760, View in Reaxys; Michalek; Journal of the American Chemical Society; vol. 52; (1930); p. 4358,4360, View in Reaxys 17 of 23

Melting Point [°C]

89 - 90

Levine; Hauser; Journal of the American Chemical Society; vol. 68; (1946); p. 760, View in Reaxys 18 of 23

Melting Point [°C]

87

Solvent (Melting Point)

methanol

Bobranskii; Drabik; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 14; (1941); p. 410,413; Chem.Abstr.; (1942); p. 2531, View in Reaxys 19 of 23

Melting Point [°C]

90 - 91

Solvent (Melting Point)

benzene

Bougault; Bulletin de la Societe Chimique de France; vol. <4> 21; (1917); p. 187, View in Reaxys 20 of 23

Melting Point [°C]

90 - 91

Solvent (Melting Point)

ethyl acetate; light petroleum

Bougault; Bulletin de la Societe Chimique de France; vol. <4> 21; (1917); p. 187, View in Reaxys 21 of 23

Melting Point [°C]

90

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Beckh; Chemische Berichte; vol. 31; (1898); p. 3163, View in Reaxys 22 of 23

Melting Point [°C]

89 - 90

Solvent (Melting Point)

aq. ethanol

Walther; Schickler; Journal fuer Praktische Chemie (Leipzig); vol. <2> 55; (1897); p. 323, View in Reaxys 23 of 23

Melting Point [°C]

89 - 90

Solvent (Melting Point)

ethyl acetate; petroleum ether

Walther; Schickler; Journal fuer Praktische Chemie (Leipzig); vol. <2> 55; (1897); p. 323, View in Reaxys Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

Kim, Bo Ram; Lee, Hyung-Geun; Kang, Seung-Beom; Jung, Kwang-Ju; Sung, Gi Hyeon; Kim, JeumJong; Lee, Sang-Gyeong; Yoon, Yong-Jin; Tetrahedron; vol. 69; nb. 48; (2013); p. 10331 - 10336, View in Reaxys

Crystal Property Description (7) Colour & Other Location Properties yellow

References Kim, Bo Ram; Lee, Hyung-Geun; Kang, Seung-Beom; Jung, Kwang-Ju; Sung, Gi Hyeon; Kim, Jeum-Jong; Lee, Sang-Gyeong; Yoon, Yong-Jin; Tetrahedron; vol. 69; nb. 48; (2013); p. 10331 - 10336, View in Reaxys

light-yellow

Page/Page column 54

Patent; BIOENERGENIX; US2012/277224; (2012); (A1) English, View in Reaxys

brown

Page/Page column 74

Patent; BIOENERGENIX; US2012/277224; (2012); (A1) English, View in Reaxys

white

Patent; Bold, Guido; Floersheimer, Andreas; Furet, Pascal; Imbach, Patricia; Masuya, Keiichi; Schoepfer, Joseph G.; US2005/222171; (2005); (A1) English, View in Reaxys; Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70431; (2005); (A1) English, View in Reaxys; Patent; Sivasankaran, Rajeev; Zimmermann, Kaspar; US2009/69315; (2009); (A1) English, View in Reaxys

light-yellow

Kamila, Sukanta; Koh, Benjamin; Biehl, Edward R.; Synthetic Communications; vol. 36; nb. 23; (2006); p. 3493 - 3507, View in Reaxys; El-Hamamsy, Mervat H.R.I.; Smith, Anthony W.; Thompson, Andrew S.; Threadgill, Michael D.; Bioorganic and Medicinal Chemistry; vol. 15; nb. 13; (2007); p. 4552 - 4576, View in Reaxys

colorless

Page/Page column 97

Prismen

Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); (A1) English, View in Reaxys Bougault; Bulletin de la Societe Chimique de France; vol. <4> 21; (1917); p. 187, View in Reaxys

Dissociation Exponent (5) 1 of 5

Dissociation Exponent (pK)

-0.91

Dissociation Group

C=O (enol)

Temperature (Dissociation Exponent) [°C]

25

Solvent (Dissociation Exponent)

dimethylsulfoxide

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a1/apparent

Kern, J. M.; Sauer, J. D.; Federlin, P.; Tetrahedron; vol. 38; nb. 20; (1982); p. 3023 - 3033, View in Reaxys 2 of 5

Type (Dissociation Exponent)

a1

Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys

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3 of 5

Comment (Dissociation Exponent)

(pk')pK(a): 5.72

Cosofret et al.; Revista de Chimie (Bucharest, Romania); vol. 30; (1979); p. 580, View in Reaxys 4 of 5

Comment (Dissociation Exponent)

(pk')pK(a)

Kern; Federlin; Tetrahedron; vol. 34; (1978); p. 661,663, View in Reaxys 5 of 5

Comment (Dissociation Exponent)

(pk')pK

Le Guillanton; Bulletin de la Societe Chimique de France; (1973); p. 3458,3459, 3460, View in Reaxys Electrochemical Behaviour (2) Description (Elec- References trochemical Behaviour) Electrolytic dissociation / protonation equilibrium

Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys

Electrochemical properties

Cosofret et al.; Revista de Chimie (Bucharest, Romania); vol. 30; (1979); p. 580, View in Reaxys

Electrochemical Characteristics (2) 1 of 2

Description (Electrochemical Characteristics)

oxidation potential

Kern; Federlin; Journal of Electroanalytical Chemistry and Interfacial Electrochemistry; vol. 96; (1979); p. 209,214,218, View in Reaxys; Kern; Federlin; Tetrahedron Letters; (1977); p. 837,838, View in Reaxys; Kern, J. M.; Sauer, J. D.; Federlin, P.; Tetrahedron; vol. 38; nb. 20; (1982); p. 3023 - 3033, View in Reaxys 2 of 2

Description (Electrochemical Characteristics)

polarographic half-wave potential

Le Guillanton; Bulletin de la Societe Chimique de France; (1973); p. 3458,3459, 3460, View in Reaxys Further Information (1) Description (Fur- References ther Information) Further information

Ravoux,J.-P.; Decombe,J.; Bulletin de la Societe Chimique de France; (1969); p. 146 - 153, View in Reaxys

NMR Spectroscopy (15) 1 of 15

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

1H

Coupling Nuclei

1H

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

300

Location

supporting information

Kim, Bo Ram; Lee, Hyung-Geun; Kang, Seung-Beom; Jung, Kwang-Ju; Sung, Gi Hyeon; Kim, Jeum-Jong; Lee, Sang-Gyeong; Yoon, Yong-Jin; Tetrahedron; vol. 69; nb. 48; (2013); p. 10331 - 10336, View in Reaxys 2 of 15

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

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Frequency (NMR Spectroscopy) [MHz]

75

Location

supporting information

Kim, Bo Ram; Lee, Hyung-Geun; Kang, Seung-Beom; Jung, Kwang-Ju; Sung, Gi Hyeon; Kim, Jeum-Jong; Lee, Sang-Gyeong; Yoon, Yong-Jin; Tetrahedron; vol. 69; nb. 48; (2013); p. 10331 - 10336, View in Reaxys 3 of 15

Nucleus (NMR Spectroscopy)

1H

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

300

Original Text (NMR Spectroscopy)

1H-NMR

Location

Page/Page column 54

Comment (NMR Spectroscopy)

Signals given

(300 MHz, CDCl3) δ 7.40-7.50 (m, 5H), 4.70 (s, 1H), 2.29 (s, 3H)

Signals [ppm]

7.4 - 7.5; 4.7; 2.29

Kind of signal

m, 5H; s, 1H; s, 3H

Patent; BIOENERGENIX; US2012/277224; (2012); (A1) English, View in Reaxys 4 of 15

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.84; 7.04; 6.68; 3.21; 2.03

Kind of signal

d, 9.0 Hz, 2H; t, 9.0 Hz, 2H; t, 9.0 Hz, 1H; s/broad, 1H, CH; s, 3H, CH&3%

(400 MHz, DMSO-d6): 7.84 (d, 9.0 Hz, 2H), 7.04 (t, 9.0 Hz, 2H), 6.68 (t, 9.0 Hz, 1H), 3.21 (s/broad, 1H, CH), 2.03 (s, 3H, CH3)

Patent; Sivasankaran, Rajeev; Zimmermann, Kaspar; US2009/69315; (2009); (A1) English, View in Reaxys 5 of 15

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

1H

Solvents (NMR Spectro- CDCl3 scopy) Kern, J. M.; Sauer, J. D.; Federlin, P.; Tetrahedron; vol. 38; nb. 20; (1982); p. 3023 - 3033, View in Reaxys; Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys; Itoh; Fukuda; Fujisawa; Bulletin of the Chemical Society of Japan; vol. 62; nb. 12; (1989); p. 3851 - 3855, View in Reaxys; El-Hamamsy, Mervat H.R.I.; Smith, Anthony W.; Thompson, Andrew S.; Threadgill, Michael D.; Bioorganic and Medicinal Chemistry; vol. 15; nb. 13; (2007); p. 4552 - 4576, View in Reaxys 6 of 15

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

1H

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

400

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Kamila, Sukanta; Koh, Benjamin; Biehl, Edward R.; Synthetic Communications; vol. 36; nb. 23; (2006); p. 3493 3507, View in Reaxys 7 of 15

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Kamila, Sukanta; Koh, Benjamin; Biehl, Edward R.; Synthetic Communications; vol. 36; nb. 23; (2006); p. 3493 3507, View in Reaxys 8 of 15

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1H-NMR

Location

Page/Page column 97

Comment (NMR Spectroscopy)

Signals given

(CDCl3)δ: 2.27 (3H, s), 4.68 (1H, s), 7.36-7.52 (5H, m).

Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); (A1) English, View in Reaxys 9 of 15

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR (400 MHz, DMSO-d6): 7.84 (d, 9.0 Hz, 2H), 7.04 (t, 9.0 Hz, 2H), 6.68 (t, 9.0 Hz, 1H), 3.21 (s/broad, 1H, CH), 2.03 (s, 3H, CH3)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.84; 7.04; 6.68; 3.21; 2.03

Kind of signal

d, 9.0 Hz, 2H; t, 9.0 Hz, 2H; t, 9.0 Hz, 1H; s/broad, 1H, CH; s, 3H, CH&3%

Patent; Bold, Guido; Floersheimer, Andreas; Furet, Pascal; Imbach, Patricia; Masuya, Keiichi; Schoepfer, Joseph G.; US2005/222171; (2005); (A1) English, View in Reaxys 10 of 15

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

'H-NMR (400 MHz, DMSO-de) : 7.84 (d, 9.0 Hz, 2H), 7.04 (t, 9.0 Hz, 2H), 6.68 (t, 9.0 Hz, 1H), 3.21 (s/broad, 1H, CH), 2.03 (s, 3H, CH3).

Comment (NMR Spectroscopy)

Signals given

Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70431; (2005); (A1) English, View in Reaxys 11 of 15

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

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

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Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys 12 of 15

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

1H

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys 13 of 15

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

1H

Solvents (NMR Spectro- ethanol-d6 scopy) Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys 14 of 15

Description (NMR Spec- NMR troscopy) De Jongh et al.; Journal of Organic Chemistry; vol. 36; (1971); p. 3160,3167, View in Reaxys

15 of 15

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

1H

Aspart-Pascot,L.; Lematre,J.; Bulletin de la Societe Chimique de France; (1971); p. 483 - 490, View in Reaxys IR Spectroscopy (6) 1 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Kim, Bo Ram; Lee, Hyung-Geun; Kang, Seung-Beom; Jung, Kwang-Ju; Sung, Gi Hyeon; Kim, Jeum-Jong; Lee, Sang-Gyeong; Yoon, Yong-Jin; Tetrahedron; vol. 69; nb. 48; (2013); p. 10331 - 10336, View in Reaxys 2 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3050 - 1140 cm**(-1)

Itoh; Fukuda; Fujisawa; Bulletin of the Chemical Society of Japan; vol. 62; nb. 12; (1989); p. 3851 - 3855, View in Reaxys 3 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

2240 - 1640 cm**(-1)

Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

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Comment (IR Spectroscopy)

2245 - 1735 cm**(-1)

Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys 5 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

3100 - 1635 cm**(-1)

Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys 6 of 6

Description (IR Spectroscopy)

Bands

Aspart-Pascot,L.; Lematre,J.; Bulletin de la Societe Chimique de France; (1971); p. 483 - 490, View in Reaxys Mass Spectrometry (6) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

Peak

high resolution mass spectrometry (HRMS); electron impact (EI); spectrum

Kim, Bo Ram; Lee, Hyung-Geun; Kang, Seung-Beom; Jung, Kwang-Ju; Sung, Gi Hyeon; Kim, Jeum-Jong; Lee, Sang-Gyeong; Yoon, Yong-Jin; Tetrahedron; vol. 69; nb. 48; (2013); p. 10331 - 10336, View in Reaxys

ESI (Electrospray ionisation) FAB (Fast atom bombardment)

References

Molecular peak

Page/Page column 97

157.9 m/z

Molecular peak

Patent; Sivasankaran, Rajeev; Zimmermann, Kaspar; US2009/69315; (2009); (A1) English, View in Reaxys Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); (A1) English, View in Reaxys

spectrum

Pavlik, James W.; St. Martin, Heather; Lambert, Karen A.; Lowell, Jennifer A.; Tsefrikas, Vikki M.; Eddins, Cheryl K.; Kebede, Naod; Journal of Heterocyclic Chemistry; vol. 42; nb. 2; (2005); p. 273 - 281, View in Reaxys

ESI (Electrospray ionisation)

Molecular peak

Patent; Bold, Guido; Floersheimer, Andreas; Furet, Pascal; Imbach, Patricia; Masuya, Keiichi; Schoepfer, Joseph G.; US2005/222171; (2005); (A1) English, View in Reaxys

ESI (Electrospray ionisation)

Molecular peak

Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70431; (2005); (A1) English, View in Reaxys

UV/VIS Spectroscopy (3) 1 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 263.5 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

11780

Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys 2 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

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

13760

Bankowska, Zofia; Krawczyk, Marta; Polish Journal of Chemistry; vol. 55; nb. 3; (1981); p. 623 - 630, View in Reaxys 3 of 3

Description (UV/VIS Spectroscopy)

UV/VIS

Le Guillanton; Bulletin de la Societe Chimique de France; (1973); p. 3458,3459, 3460, View in Reaxys

Reaxys ID 4038276 View in Reaxys

2/2 CAS Registry Number: 70230-40-9 Chemical Name: α-Acetyl-α-cyan-benzyl-Na Linear Structure Formula: C10H8NO(1-)*Na(1+) Molecular Formula: C10H8NO*Na Molecular Weight: 181.169 Type of Substance: isocyclic InChI Key: AMOQCIAUXQQACG-UHFFFAOYSA-N Note:

N C– O Na +

Substance Label (2) Label References 2a

Filimonov; Chirkova; Sharunov; Abramov; Stashina; Firgang; Suponitsky; Chemistry of Heterocyclic Compounds; vol. 48; nb. 3; (2012); p. 427 - 435, View in Reaxys

15(-)

Abbotto, Alessandro; Bradamante, Silvia; Pagani, Giorgio A.; Journal of Organic Chemistry; vol. 58; nb. 2; (1993); p. 449 - 455, View in Reaxys

NMR Spectroscopy (1) 1 of 1

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

13C

Solvents (NMR Spectro- dimethylsulfoxide scopy) Temperature (NMR Spectroscopy) [°C]

25

Abbotto, Alessandro; Bradamante, Silvia; Pagani, Giorgio A.; Journal of Organic Chemistry; vol. 58; nb. 2; (1993); p. 449 - 455, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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