5-(Bromomethyl)-1,3-benzodioxole [C8H7BrO2]

Query Query Br

Results

Date

3 substances in Reaxys

2018-02-09 04h:57m:05s (EST)

O

1. Query O

Search as: As drawn

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2018-02-09 05:02:19

Reaxys ID 135376 View in Reaxys

Br

1/3 CAS Registry Number: 2606-51-1 Chemical Name: 3,4-Methylenedioxybenzyl bromide; 3,4methylenedioxybenzyl bromide; 5-(bromomethyl)-1,3-benzodioxole Linear Structure Formula: BrCH2C6H3(OCH2O) Molecular Formula: C8H7BrO2 Molecular Weight: 215.046 Type of Substance: heterocyclic InChI Key: UNYHRXLMTSXVIB-UHFFFAOYSA-N Note:

O O

Substance Label (40) Label References 5m

Mohsin, Noor-ul-Amin; Seebacher, Werner; Faist, Johanna; Hochegger, Patrick; Kaiser, Marcel; Mäser, Pascal; Belaj, Ferdinand; Saf, Robert; Kretschmer, Nadine; Alajlani, Muaaz; Turek, Ivana; Brantner, Adelheid; Bauer, Rudolf; Bucar, Franz; Weis, Robert; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 97 - 106, View in Reaxys

2

González-Calderón, Davir; Aguirre-De Paz, José G.; González-González, Carlos A.; Fuentes-Benítes, Aydeé; González-Romero, Carlos; Tetrahedron Letters; vol. 56; nb. 13; (2015); p. 1713 - 1715, View in Reaxys; Procter, Richard J.; Dunsford, Jay J.; Rushworth, Philip J.; Hulcoop, David G.; Layfield, Richard A.; Ingleson, Michael J.; Chemistry - A European Journal; vol. 23; nb. 63; (2017); p. 15889 15893, View in Reaxys

9

Diaz-Muñoz, Gaspar; Isidorio, Raquel Geralda; Miranda, Izabel Luzia; de Souza Dias, Gabriel Nunes; Diaz, Marisa Alves Nogueira; Tetrahedron Letters; vol. 58; nb. 33; (2017); p. 3311 - 3315, View in Reaxys

26a

Wu, Deyan; Zhang, Tianhua; Chen, Yiping; Huang, Yadan; Geng, Haiju; Yu, Yanfa; Zhang, Chen; Lai, Zengwei; Wu, Yinuo; Guo, Xiaolei; Chen, Jianwen; Luo, Hai-Bin; Journal of Medicinal Chemistry; vol. 60; nb. 15; (2017); p. 6622 - 6637, View in Reaxys

Compound h

Patent; RIKEN; Nakano, Takeshi; ASAMI, Tadao; OSADA, Hiroyuki; (31 pag.); US2017/305886; (2017); (A1) English, View in Reaxys

14d

Wu, Xi-Shan; Wang, Rui; Xing, Yan-Li; Xue, Xiao-Qian; Zhang, Yan; Lu, Yong-Zhi; Song, Yu; Luo, XiaoYu; Wu, Chun; Zhou, Yu-Lai; Jiang, Jian-Qin; Xu, Yong; Acta Pharmacologica Sinica; vol. 37; nb. 11; (2016); p. 1516 - 1524, View in Reaxys

4o

Howieson, Vanessa M.; Tran, Elisa; Hoegl, Annabelle; Fam, Han Ling; Fu, Jonathan; Sivonen, Kate; Li, Xiao Xuan; Auclair, Karine; Saliba, Kevin J.; Antimicrobial Agents and Chemotherapy; vol. 60; nb. 12; (2016); p. 7146 - 7152, View in Reaxys

1

Fallon, Brendan J.; Corcé, Vincent; Amatore, Muriel; Aubert, Corinne; Chemla, Fabrice; Ferreira, Franck; Perez-Luna, Alejandro; Petit, Marc; New Journal of Chemistry; vol. 40; nb. 12; (2016); p. 9912 9916, View in Reaxys

16f

Aidhen, Indrapal S.; Mukkamala, Ramesh; Weidner, Christopher; Sauer, Sascha; Organic Letters; vol. 17; nb. 2; (2015); p. 194 - 197, View in Reaxys

19

Drew; Lawrence; Sherburn; Chemical Science; vol. 6; nb. 7; (2015); p. 3886 - 3890, View in Reaxys

2j

Huang, Ju; Liu, Hongtao; Liu, Mingliang; Zhang, Rui; Li, Linhu; Wang, Bin; Wang, Minghua; Wang, Chunlan; Lu, Yu; Bioorganic and Medicinal Chemistry Letters; vol. 25; nb. 22; (2015); p. 5058 - 5063, View in Reaxys

8

Schaefer, Mark; Hanik, Nils; Kilbinger, Andreas F. M.; Macromolecules; vol. 45; nb. 17; (2012); p. 6807 6818, View in Reaxys; Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Angewandte Chemie - International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 - 4318,4, View in Reaxys; Astrand, O. Alexander H.; Sandberg, Marcel; Sylte, Ingebrigt; Goerbitz, Carl Henrik; Thoresen, G. Hege; Kase, Eili T.; Rongved, Pal; Bioorganic and Medicinal Chemistry; vol. 22; nb. 1; (2014); p. 643 - 650, View in Reaxys

18

Tuley, Alfred; Wang, Yane-Shih; Fang, Xinqiang; Kurra, Yadagiri; Rezenom, Yohannes H.; Liu, Wenshe R.; Chemical Communications; vol. 50; nb. 20; (2014); p. 2673 - 2675, View in Reaxys

5k

Sato, Kazuyuki; Inoue, Yuichi; Mori, Tomohisa; Sakaue, Atsushi; Tarui, Atsushi; Omote, Masaaki; Kumadaki, Itsumaro; Ando, Akira; Organic Letters; vol. 16; nb. 14; (2014); p. 3756 - 3759, View in Reaxys

65p

Yao, Yiwu; Liao, Chenzhong; Li, Zheng; Wang, Zhen; Sun, Qiao; Liu, Chunping; Yang, Yang; Tu, Zhengchao; Jiang, Sheng; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 639 - 652, View in Reaxys

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26

Hu, Weimin; Qin, Hua; Cui, Yuxin; Jia, Yanxing; Chemistry - A European Journal; vol. 19; nb. 9; (2013); p. 3139 - 3147, View in Reaxys

53

Sun, Qiao; Yao, Yiwu; Liu, Chunping; Li, Hua; Yao, Hequan; Xue, Xiaowen; Liu, Jinsong; Tu, Zhengchao; Jiang, Sheng; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 11; (2013); p. 3295 - 3299, View in Reaxys

6a

Feng, Lianshun; Lv, Kai; Liu, Mingliang; Wang, Shuo; Zhao, Jing; You, Xuefu; Li, Sujie; Cao, Jue; Guo, Huiyuan; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 125 - 136, View in Reaxys

3k

Tynebor, Robert M.; Chen, Meng-Hsin; Natarajan, Swaminathan R.; O'Neill, Edward A.; Thompson, James E.; Fitzgerald, Catherine E.; O'Keefe, Stephen J.; Doherty, James B.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 18; (2012); p. 5971 - 5975, View in Reaxys

2l

Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467,4, View in Reaxys; Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467, View in Reaxys

55

Nicolaou; Lister, Troy; Denton, Ross M.; Gelin, Christine F.; Tetrahedron; vol. 64; nb. 21; (2008); p. 4736 - 4757, View in Reaxys

38

Angle, Steven R.; Choi, Inchang; Tham, Fook S.; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6268 - 6278, View in Reaxys

Table1, entry17, RBr

Ranu, Brindaban C.; Banerjee, Subhash; Adak, Laksmikanta; Tetrahedron Letters; vol. 48; nb. 41; (2007); p. 7374 - 7379, View in Reaxys

3

Yoh, Soo-Dong; Cheong, Duk-Young; Lee, Chung-Heun; Kim, Sung-Hong; Park, Jong-Hwan; Fujio, Mizue; Tsuno, Yuho; Journal of Physical Organic Chemistry; vol. 14; nb. 3; (2001); p. 123 - 130, View in Reaxys; Harayama, Takashi; Hori, Akihiro; Abe, Hitoshi; Takeuchi, Yasuo; Heterocycles; vol. 67; nb. 1; (2006); p. 385 - 390, View in Reaxys; Imperio, Daniela; Pirali, Tracey; Galli, Ubaldina; Pagliai, Francesca; Cafici, Laura; Canonico, Pier Luigi; Sorba, Giovanni; Genazzani, Armando A.; Tron, Gian Cesare; Bioorganic and Medicinal Chemistry; vol. 15; nb. 21; (2007); p. 6748 - 6757, View in Reaxys

14a

Aslam, Shazia N.; Stevenson, Philip C.; Phythian, Sara J.; Veitch, Nigel C.; Hall, David R.; Tetrahedron; vol. 62; nb. 17; (2006); p. 4214 - 4226, View in Reaxys

13d

Raffaelli, Barbara; Waehaelae, Kristiina; Hase, Tapio; Organic and Biomolecular Chemistry; vol. 4; nb. 2; (2006); p. 331 - 341, View in Reaxys

Table 1

Elango, Shanmugam; Venugopal, Murugapillai; Suresh; Eni; Tetrahedron; vol. 61; nb. 6; (2005); p. 1443 1447, View in Reaxys

table 1, entry 5

Ranu, Brindaban C.; Jana, Ranjan; Advanced Synthesis and Catalysis; vol. 347; nb. 14; (2005); p. 1811 1818, View in Reaxys

educt to 4

Huther, Nathalie; McGrail, P. Terry; Parsons, Andrew F.; European Journal of Organic Chemistry; nb. 8; (2004); p. 1740 - 1749, View in Reaxys

2, entry 17

Bandgar, Babasaheb P.; Bettigeri, Sampada V.; Monatshefte fur Chemie; vol. 135; nb. 10; (2004); p. 1251 - 1255, View in Reaxys

4

Enders, Dieter; Backes, Michael; Tetrahedron Asymmetry; vol. 15; nb. 11; (2004); p. 1813 - 1817, View in Reaxys

Tab 1/7,2/6 RX

Ranu, Brindaban C.; Mandal, Tanmay; Journal of Organic Chemistry; vol. 69; nb. 17; (2004); p. 5793 5795, View in Reaxys

3,4Pohmakotr, Manat; Soorukram, Darunee; Tuchinda, Patoomratana; Prabpai, Samran; Kongsaeree, CH2(O)2PhCH2B Palangpon; Reutrakul, Vichai; Tetrahedron Letters; vol. 45; nb. 22; (2004); p. 4315 - 4318, View in Reaxys r Ar2CH2X for 26

Vanotti, Ermes; Bargiotti, Alberto; Biancardi, Roberto; Pinciroli, Vittorio; Ermoli, Antonella; Menichincheri, Maria; Tibolla, Marcello; Tetrahedron; vol. 58; nb. 17; (2002); p. 3361 - 3370, View in Reaxys

9a

Elango, Shanmugham; Wang, Ying-Chuan; Cheng, Chien-Liang; Yan, Tu-Hsin; Tetrahedron Letters; vol. 43; nb. 20; (2002); p. 3757 - 3759, View in Reaxys

6

Harrowven, David C.; Nunn, Michael I.T.; Blumire, Nigel J.; Fenwick, David R.; Tetrahedron; vol. 57; nb. 20; (2001); p. 4447 - 4454, View in Reaxys

23a

Hirano; Osawa; Yamaoka; Yokoi; Biological and Pharmaceutical Bulletin; vol. 24; nb. 11; (2001); p. 1277 1281, View in Reaxys

8h

Kamlage; Sefkow; Pool-Zobel; Peter; Chemical Communications; nb. 4; (2001); p. 331 - 332, View in Reaxys

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13

Ollero, Lourdes; Castedo, Luis; Dominguez, Domingo; Tetrahedron; vol. 55; nb. 14; (1999); p. 4445 4456, View in Reaxys

42

Pearson, William H.; Stevens, Erland P.; Journal of Organic Chemistry; vol. 63; nb. 26; (1998); p. 9812 9827, View in Reaxys

Patent-Specific Data (2) References Patent; RIKEN; Nakano, Takeshi; ASAMI, Tadao; OSADA, Hiroyuki; (31 pag.); US2017/305886; (2017); (A1) English, View in Reaxys Patent; Glacera Contour, Marie-Odile; Sidhu, Alban; Roubert, Pierre; Thurieau, Christophe; US2005/154039; (2005); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.312

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

1

TPSA

18.46

Lipinski Number

4

Veber Number

2

Melting Point (9) 1 of 9

Melting Point [°C]

51 - 53

Solvent (Melting Point)

Petroleum ether

Location

supporting information

Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Angewandte Chemie - International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 - 4318,4, View in Reaxys 2 of 9

Melting Point [°C]

43 - 44

Location

supporting information

Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467,4, View in Reaxys; Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467, View in Reaxys 3 of 9

Melting Point [°C]

39

Angle, Steven R.; Choi, Inchang; Tham, Fook S.; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6268 6278, View in Reaxys 4 of 9

Melting Point [°C]

97 - 98

Imperio, Daniela; Pirali, Tracey; Galli, Ubaldina; Pagliai, Francesca; Cafici, Laura; Canonico, Pier Luigi; Sorba, Giovanni; Genazzani, Armando A.; Tron, Gian Cesare; Bioorganic and Medicinal Chemistry; vol. 15; nb. 21; (2007); p. 6748 - 6757, View in Reaxys 5 of 9

Melting Point [°C]

45 - 47

Aslam, Shazia N.; Stevenson, Philip C.; Phythian, Sara J.; Veitch, Nigel C.; Hall, David R.; Tetrahedron; vol. 62; nb. 17; (2006); p. 4214 - 4226, View in Reaxys 6 of 9

Melting Point [°C]

45.6 - 47.2

Solvent (Melting Point)

hexane

Van Oeveren; Jansen; Feringa; Journal of Organic Chemistry; vol. 59; nb. 20; (1994); p. 5999 - 6007, View in Reaxys 7 of 9

Melting Point [°C]

49 - 50

Weinstein,B.; Craig,A.R.; Journal of Organic Chemistry; vol. 41; nb. 5; (1976); p. 875 - 878, View in Reaxys 8 of 9

Melting Point [°C]

48

MAMALIS; GREEN; OUTRED; RIX; Journal of the Chemical Society; vol. 65; (1965); p. 1829 - 1843, View in Reaxys 9 of 9

Melting Point [°C]

49

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Solvent (Melting Point)

light petroleum

Robinsin,G. M.; Robinson,R.; Journal of the Chemical Society; vol. 105; (1914); p. 1463, View in Reaxys Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

110

5

Mitra, Jayati; Mitra, Alok Kumar; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 33; nb. 10; (1994); p. 953 - 956, View in Reaxys

101 - 103

0.1

MAMALIS; GREEN; OUTRED; RIX; Journal of the Chemical Society; vol. 65; (1965); p. 1829 - 1843, View in Reaxys

Chromatographic Data (1) Chromatographic Location data TLC (Thin layer chromatography)

supporting information

Crystal Property Description (6) Colour & Other Location Properties

References Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467, View in Reaxys; Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Angewandte Chemie - International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 4318,4, View in Reaxys References

beige

supporting information

González-Calderón, Davir; Aguirre-De Paz, José G.; González-González, Carlos A.; Fuentes-Benítes, Aydeé; González-Romero, Carlos; Tetrahedron Letters; vol. 56; nb. 13; (2015); p. 1713 - 1715, View in Reaxys

white

supporting information

Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Angewandte Chemie International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 - 4318,4, View in Reaxys

green

supporting information

Roper, Kimberley A.; Lange, Heiko; Polyzos, Anastasios; Berry, Malcolm B.; Baxendale, Ian R.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 1648 - 1655, View in Reaxys

pink

supporting information

Yu, Wing-Yiu; Tsoi, Yuk-Tai; Zhou, Zhongyuan; Chan, Albert S. C.; Organic Letters; vol. 11; nb. 2; (2009); p. 469 - 472, View in Reaxys

light-yellow

Angle, Steven R.; Choi, Inchang; Tham, Fook S.; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6268 - 6278, View in Reaxys

Nadeln

Robinsin,G. M.; Robinson,R.; Journal of the Chemical Society; vol. 105; (1914); p. 1463, View in Reaxys

NMR Spectroscopy (23) 1 of 23

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

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

20

Frequency (NMR Spectroscopy) [MHz]

400

Wu, Deyan; Zhang, Tianhua; Chen, Yiping; Huang, Yadan; Geng, Haiju; Yu, Yanfa; Zhang, Chen; Lai, Zengwei; Wu, Yinuo; Guo, Xiaolei; Chen, Jianwen; Luo, Hai-Bin; Journal of Medicinal Chemistry; vol. 60; nb. 15; (2017); p. 6622 - 6637, View in Reaxys 2 of 23

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

1H

Solvents (NMR Spectro- chloroform-d1 scopy)

5/12

2018-02-09 05:02:19

Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

González-Calderón, Davir; Aguirre-De Paz, José G.; González-González, Carlos A.; Fuentes-Benítes, Aydeé; González-Romero, Carlos; Tetrahedron Letters; vol. 56; nb. 13; (2015); p. 1713 - 1715, View in Reaxys 3 of 23

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

13C

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

75

Location

supporting information

González-Calderón, Davir; Aguirre-De Paz, José G.; González-González, Carlos A.; Fuentes-Benítes, Aydeé; González-Romero, Carlos; Tetrahedron Letters; vol. 56; nb. 13; (2015); p. 1713 - 1715, View in Reaxys 4 of 23

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

1H

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

400

Original Text (NMR Spectroscopy)

1H NMR (400 MHz, CDCI3) 6: 3.84 (s, 3H), 3.87 (s, 6H), 4.47(s, 2H), 6.62 (s, 2H).

Location

Page/Page column 55

Patent; DUBLIN CITY UNIVERSITY; O'BRIEN, Christopher; WO2014/140353; (2014); (A1) English, View in Reaxys 5 of 23

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

1H

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

400.1

Location

supporting information

Coyle, Emma E.; Doonan, Bryan J.; Holohan, Andrew J.; Walsh, Killian A.; Lavigne, Florie; Krenske, Elizabeth H.; O'Brien, Christopher J.; Angewandte Chemie - International Edition; vol. 53; nb. 47; (2014); p. 12907 12911; Angew. Chem.; vol. 126; nb. 47; (2014); p. 13121 - 13125,5, View in Reaxys 6 of 23

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

1H

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

400

Location

supporting information

Qin, Hua; Xu, Zhengren; Cui, Yuxin; Jia, Yanxing; Angewandte Chemie - International Edition; vol. 50; nb. 19; (2011); p. 4447 - 4449, View in Reaxys; Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Ange-

6/12

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wandte Chemie - International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 - 4318,4, View in Reaxys 7 of 23

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

13C

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

100

Location

supporting information

Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467, View in Reaxys; Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Angewandte Chemie - International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 - 4318,4, View in Reaxys 8 of 23

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

13C

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

100

Location

supporting information

Qin, Hua; Xu, Zhengren; Cui, Yuxin; Jia, Yanxing; Angewandte Chemie - International Edition; vol. 50; nb. 19; (2011); p. 4447 - 4449, View in Reaxys; Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467,4, View in Reaxys 9 of 23

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

1H

Schaefer, Mark; Hanik, Nils; Kilbinger, Andreas F. M.; Macromolecules; vol. 45; nb. 17; (2012); p. 6807 - 6818, View in Reaxys 10 of 23

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

Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467,4, View in Reaxys; Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467, View in Reaxys 11 of 23

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

1H

Solvents (NMR Spectro- chloroform-d1 scopy)

7/12

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Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Roper, Kimberley A.; Lange, Heiko; Polyzos, Anastasios; Berry, Malcolm B.; Baxendale, Ian R.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 1648 - 1655, View in Reaxys 12 of 23

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

13C

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

150

Location

supporting information

Roper, Kimberley A.; Lange, Heiko; Polyzos, Anastasios; Berry, Malcolm B.; Baxendale, Ian R.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 1648 - 1655, View in Reaxys 13 of 23

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

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Yu, Wing-Yiu; Tsoi, Yuk-Tai; Zhou, Zhongyuan; Chan, Albert S. C.; Organic Letters; vol. 11; nb. 2; (2009); p. 469 - 472, View in Reaxys 14 of 23

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Yu, Wing-Yiu; Tsoi, Yuk-Tai; Zhou, Zhongyuan; Chan, Albert S. C.; Organic Letters; vol. 11; nb. 2; (2009); p. 469 - 472, View in Reaxys 15 of 23

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

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

300

Angle, Steven R.; Choi, Inchang; Tham, Fook S.; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6268 6278, View in Reaxys

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16 of 23

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

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

75

Angle, Steven R.; Choi, Inchang; Tham, Fook S.; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6268 6278, View in Reaxys 17 of 23

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

13C

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

75

Imperio, Daniela; Pirali, Tracey; Galli, Ubaldina; Pagliai, Francesca; Cafici, Laura; Canonico, Pier Luigi; Sorba, Giovanni; Genazzani, Armando A.; Tron, Gian Cesare; Bioorganic and Medicinal Chemistry; vol. 15; nb. 21; (2007); p. 6748 - 6757, View in Reaxys; Angle, Steven R.; Choi, Inchang; Tham, Fook S.; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6268 - 6278, View in Reaxys 18 of 23

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

1H

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

300

Imperio, Daniela; Pirali, Tracey; Galli, Ubaldina; Pagliai, Francesca; Cafici, Laura; Canonico, Pier Luigi; Sorba, Giovanni; Genazzani, Armando A.; Tron, Gian Cesare; Bioorganic and Medicinal Chemistry; vol. 15; nb. 21; (2007); p. 6748 - 6757, View in Reaxys; Angle, Steven R.; Choi, Inchang; Tham, Fook S.; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6268 - 6278, View in Reaxys 19 of 23

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

1H

Solvents (NMR Spectro- CDCl3 scopy) Beard, Andrew R.; Hazell, Sarah J.; Mann, John; Palmer, Christopher; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1993); p. 1235 - 1238, View in Reaxys; Asakawa, Yoshinori; Takikawa, Keiko; Tori, Motoo; Phytochemistry (Elsevier); vol. 26; nb. 4; (1987); p. 1023 1026, View in Reaxys; Van Oeveren; Jansen; Feringa; Journal of Organic Chemistry; vol. 59; nb. 20; (1994); p. 5999 - 6007, View in Reaxys; Mitra, Jayati; Mitra, Alok Kumar; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 33; nb. 10; (1994); p. 953 - 956, View in Reaxys; Yoh, Soo-Dong; Cheong, Duk-Young; Lee, Chung-Heun; Kim, Sung-Hong; Park, Jong-Hwan; Fujio, Mizue; Tsuno, Yuho; Journal of Physical Organic Chemistry; vol. 14; nb. 3; (2001); p. 123 - 130, View in Reaxys; Aslam, Shazia N.; Stevenson, Philip C.; Phythian, Sara J.; Veitch, Nigel C.; Hall, David R.; Tetrahedron; vol. 62; nb. 17; (2006); p. 4214 4226, View in Reaxys; Hirano; Osawa; Yamaoka; Yokoi; Biological and Pharmaceutical Bulletin; vol. 24; nb. 11; (2001); p. 1277 - 1281, View in Reaxys 20 of 23

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

13C

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Solvents (NMR Spectro- CDCl3 scopy) Van Oeveren; Jansen; Feringa; Journal of Organic Chemistry; vol. 59; nb. 20; (1994); p. 5999 - 6007, View in Reaxys; Mitra, Jayati; Mitra, Alok Kumar; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 33; nb. 10; (1994); p. 953 - 956, View in Reaxys; Aslam, Shazia N.; Stevenson, Philip C.; Phythian, Sara J.; Veitch, Nigel C.; Hall, David R.; Tetrahedron; vol. 62; nb. 17; (2006); p. 4214 - 4226, View in Reaxys; Hirano; Osawa; Yamaoka; Yokoi; Biological and Pharmaceutical Bulletin; vol. 24; nb. 11; (2001); p. 1277 - 1281, View in Reaxys 21 of 23

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- CDCl3 scopy) Aslam, Shazia N.; Stevenson, Philip C.; Phythian, Sara J.; Veitch, Nigel C.; Hall, David R.; Tetrahedron; vol. 62; nb. 17; (2006); p. 4214 - 4226, View in Reaxys; Hirano; Osawa; Yamaoka; Yokoi; Biological and Pharmaceutical Bulletin; vol. 24; nb. 11; (2001); p. 1277 - 1281, View in Reaxys 22 of 23

Nucleus (NMR Spectroscopy)

1H

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

400

Original Text (NMR Spectroscopy)

NMR 1H (DMSO-d6, 400 MHz) δ: 7.02-6.98 (m, 1H, arom.); 6.96-6.93 (m, 1H, arom); 6.88-6.86 (m, 1H, arom); 6.02 (s, 2H, CH2); 4.66 (s, 2H, CH2).

Comment (NMR Spectroscopy)

Signals given

Patent; Glacera Contour, Marie-Odile; Sidhu, Alban; Roubert, Pierre; Thurieau, Christophe; US2005/154039; (2005); (A1) English, View in Reaxys 23 of 23

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Van Oeveren; Jansen; Feringa; Journal of Organic Chemistry; vol. 59; nb. 20; (1994); p. 5999 - 6007, View in Reaxys; Mitra, Jayati; Mitra, Alok Kumar; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 33; nb. 10; (1994); p. 953 - 956, View in Reaxys IR Spectroscopy (6) 1 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Angewandte Chemie - International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 - 4318,4, View in Reaxys 2 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Location

supporting information

Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467,4, View in Reaxys; Pelletier, Guillaume; Lie, Sharon; Mousseau, James J.; Charette, Andre B.; Organic Letters; vol. 14; nb. 21; (2012); p. 5464 - 5467, View in Reaxys

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3 of 6

Description (IR Spectroscopy)

ATR-FTIR (attenuated total reflectance Fourier transform infrared spectroscopy); Intensity of IR bands; Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Roper, Kimberley A.; Lange, Heiko; Polyzos, Anastasios; Berry, Malcolm B.; Baxendale, Ian R.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 1648 - 1655, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Imperio, Daniela; Pirali, Tracey; Galli, Ubaldina; Pagliai, Francesca; Cafici, Laura; Canonico, Pier Luigi; Sorba, Giovanni; Genazzani, Armando A.; Tron, Gian Cesare; Bioorganic and Medicinal Chemistry; vol. 15; nb. 21; (2007); p. 6748 - 6757, View in Reaxys 5 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1600 - 1450 cm**(-1)

Mitra, Jayati; Mitra, Alok Kumar; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 33; nb. 10; (1994); p. 953 - 956, View in Reaxys 6 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Comment (IR Spectroscopy)

1490 - 930 cm**(-1)

Briggs et al.; Analytical Chemistry; vol. 29; (1957); p. 904,905, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry)

References

electron impact (EI); IT (ion trap); spectrum

supporting information

Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Angewandte Chemie International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 - 4318,4, View in Reaxys

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

supporting information

Drew, Samuel L.; Lawrence, Andrew L.; Sherburn, Michael S.; Angewandte Chemie International Edition; vol. 52; nb. 15; (2013); p. 4221 - 4224; Angew. Chem.; vol. 125; nb. 15; (2013); p. 4315 - 4318,4, View in Reaxys

HRMS (High res- supporting inforolution mass mation spectrometry); EI (Electron impact); FT-ICR (Fourier transform ion cyclotron resonance); Spectrum

Roper, Kimberley A.; Lange, Heiko; Polyzos, Anastasios; Berry, Malcolm B.; Baxendale, Ian R.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 1648 - 1655, View in Reaxys

spectrum; electron impact (EI)

Aslam, Shazia N.; Stevenson, Philip C.; Phythian, Sara J.; Veitch, Nigel C.; Hall, David R.; Tetrahedron; vol. 62; nb. 17; (2006); p. 4214 - 4226, View in Reaxys

Reaxys ID 23356850 View in Reaxys

2/3

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2H

O

CAS Registry Number: 1445606-00-7 Linear Structure Formula: C8H5 (2)H2BrO2 Molecular Formula: C8H7BrO2 Molecular Weight: 217.03 InChI Key: UNYHRXLMTSXVIB-APZFVMQVSA-N Note:

2H

Br

O

Substance Label (1) Label References S-2

Hu, Weimin; Qin, Hua; Cui, Yuxin; Jia, Yanxing; Chemistry - A European Journal; vol. 19; nb. 9; (2013); p. 3139 - 3147, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.312

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

1

TPSA

18.46

Lipinski Number

4

Veber Number

2

Reaxys ID 9996501 View in Reaxys

3/3 Linear Structure Formula: C7 (14)CH7BrO2 Molecular Formula: C8H7BrO2 Molecular Weight: 217.035 Type of Substance: heterocyclic InChI Key: UNYHRXLMTSXVIB-DOMIDYPGSA-N Note:

H

14C 2

Br

O O

Substance Label (1) Label References 5

Ray, Tapan; Ciszewska, Grazyna; Allentoff, Alban J.; Wu, Amy; Jones, Lawrence; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 47; nb. 14; (2004); p. 1029 - 1033, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.312

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

1

TPSA

18.46

Lipinski Number

4

Veber Number

2

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