4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile
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![4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220811/d7511fb674c24a418bbe47b941ea6fac.png "4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile")
4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile
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CAS No:
209911-63-7
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Formula:
C14H9Br2N
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Chemical Name:
4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile
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Synonyms:
2'-Cyano-4-(dibroMoMethyl)-1,1'-biphenyl;2'-Cyano-4-(dibroMoMethyl)biphenyl;4,4-DibroMoMethyl-2'-cyanobiphenyl;4'-(Dibromomethyl);4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile;[1,1'-Biphenyl]-2-carbonitrile, 4'-(dibromomethyl)-;2-(4-DibroMoMethylphenyl)benzonitrile;Valsartan Impurity 30
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CAS No:
4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile Basic Attributes
351.03596
348.910156
DTXSID40455217
2926909090
4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile Use and Manufacturing
23 g of 2-(4-methylphenyl)benzonitrile [MPB], 22g of N-bromosuccinic acid imide [NBS] and 47 mg of 2, 2'-azobis(2, 4-dimethylvaleronitrile) were suspended in 44 ml of dichoromethane, and the reaction was allowed to proceed at 45 to 50°C for 5 hours under stirring. A jacketed 1, 000 mL 3-neck flask was charged with 4'-methylbiphenyl-2-carbonitrile (Compound 1, 100.0 g) and CHProduction Example; Chlorobenzene (652.5 g) was added with 4'-methyl-2-cyanobiphenyl (416.2 g, 2.251 mole) and sodium bromate (57.41 g, 0.38 mole) dissolved in water (109 g), and the mixture was warmed at 75 to 80°C. A solution of 2, 2'-azobis(2-methylbutyronitrile) (8.31 g, 0.043 mole) dissolved in monochlorobenzene (87 g) was dropped together with bromine (217.5 g, 1.116 mole) into the mixed solution above at 70 to 80°C over 5 hours, then leaving it for 1 hour with maintaining its temperature. The solution was set still at about 80°C and then subjected to phase separation. The organic layer was added with 217.5 g of water, washed at about 80°C and then subjected to phase separation. The separated solution was concentrated under a reduced pressure to eliminate 91.4 g of chlorobenzene. The residual solution was added with 304.5 g of chlorobenzene to filter at 75 to 80°C by a filter pre-coated with 11 g of diatomaceous earth. Washing with 208.8 g of chlorobenzene, then the filtrate was cooled down after confirming no precipitation of crystal observed therein. The filtrate was added with 450 mg of seed crystal at the temperature thereof of about 50°C, and stirred at 55°C for 6 hours. Then, this solution was cooled down in the rate of 10°C/hour, followed by stirring at the temperature thereof of 30 to 35°C for 5 hours and at the temperature thereof of 0 to -5°C for 10 hours, and then being subjected to filtration. By rinsing the crystal with heptane, 404.6 g of 4'-bromomethyl-2-cyanobiphenyl was obtained in the yield of 69 percent.
A di-substituted biphenol derivative.
Computed Properties
Molecular Weight:351.04
XLogP3:4.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:350.90813
Monoisotopic Mass:348.91017
Topological Polar Surface Area:23.8
Heavy Atom Count:17
Complexity:286
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4'-(Dibromomethyl)-[1,1'-Biphenyl]-2-Carbonitrile
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