4-BROMOMETHYLBIPHENYL Chemical Properties

Melting point:

83-86 °C

Boiling point:

140 °C / 10mmHg

Density 

1.341±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Powder

color 

Pale yellow to beige

InChI

InChI=1S/C13H11Br/c14-10-11-6-8-13(9-7-11)12-4-2-1-3-5-12/h1-9H,10H2

InChIKey

HZQLUIZFUXNFHK-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC=C2)=CC=C(CBr)C=C1

CAS DataBase Reference

2567-29-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-34

Safety Statements 

37/39-26-45-36/37/39

RIDADR 

3261

HazardClass 

IRRITANT

HS Code 

29029090

MSDS

• Language:English Provider:ACROS

4-BROMOMETHYLBIPHENYL Usage And Synthesis

Chemical Properties

Pale yellow to beige powder

Uses

4-(Bromomethyl)biphenyl is a biphenyl derivative used in the preparation of various pharmaceutical compounds such as protein tyrosine phosphatase 1B inhibitors. 4-(Bromomethyl)biphenyl is useful as as atom transfer radical polymerization initiator.

Synthesis

General procedure for the synthesis of 4-bromomethylbiphenyl from 4-biphenylmethanol: Carbon tetrabromide (8.99 g, 27.1 mmol) and triphenylphosphine (7.11 g, 27.1 mmol) were sequentially added to a solution of dichloromethane (100 mL) containing biphenyl-4-ylmethanol (5.00 g, 27.1 mmol) at room temperature with continuous stirring. The reaction mixture was stirred at room temperature for 1.5 h before the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography with an eluent ratio of 1:20 ether/cyclohexane, resulting in 4-bromomethylbiphenyl (6.37 g, 95% yield) as a white solid.1H NMR (400 MHz, CDCl3) data were as follows: δ 7.60 (4H), 7.45 (4H), 7.35 (1H), 4.55 (2H).

References

[1] Organic Letters, 2013, vol. 15, # 9, p. 2210 - 2213
[2] Patent: WO2005/26120, 2005, A1. Location in patent: Page/Page column 21
[3] Patent: WO2004/110974, 2004, A1. Location in patent: Page 22
[4] Organic Letters, 2012, vol. 14, # 21, p. 5428 - 5431,4
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064

4-BROMOMETHYLBIPHENYL(2567-29-5)Related Product Information

• 4-BROMOMETHYLBIPHENYL
• 4'-BROMOMETHYLBIPHENYL-2-CARBOXYLIC
• 5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole
• 4,4'-Bis(bromomethyl)biphenyl
• METHYL-(4-BROMOMETHYLBIPHENYL-2-YL)CARBOXYLATE,4-BROMOMETHYLBIPHENYL-2-CARBONYLATE,4'-Bromomethylbiphenyl-2-carboxylate
• 4-Bromomethyl-2-cyanobiphenyl
• 3-BROMOMETHYLBIPHENYL
• 4'-(Bromomethyl)biphenyl-2-carboxamide
• 4-BROMOMETHYLBIPHENYL-2'-CARBOXYLIC ACID
• 5-[4'-(Bromomethyl)-[1,1'-biphenyl]-2-yl]-2-(triphenylmethyl)-2H-tetrazole
• 8-BROMOMETHYLFLUORANTHENE
• 2-CYANO-4-BROMO METHYL BIPHENYL
• N-Triphenylmethyl-5-(4'-bromomethylbiphenyl)-2-Tetrazole
• t-Butyl-4'(bromomethyl)-biphenyl-2-carboxylate
• 4'-BROMOMETHYL-3'-CHLORO-1,1'-BIPHENYL-2-CARBONITRILE
• 4-bromomethylbiphenyl-2'-carboxylic acid t-butyl ester
• 4-bromomethylbiphenyl-2-formic acid methyl ester
• 2-phenyl-(5-(bromomethyl)phenyl)methanamine