4-Bromo-2-cyanobenzyl bromide Chemical Properties

Boiling point:

307.2±27.0 °C(Predicted)

Density 

1.92±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

white solid

InChI

InChI=1S/C8H5Br2N/c9-4-6-1-2-8(10)3-7(6)5-11/h1-3H,4H2

InChIKey

RPQAJIVYLBTILC-UHFFFAOYSA-N

SMILES

C(#N)C1=CC(Br)=CC=C1CBr

Safety Information

HS Code 

2926907090

4-Bromo-2-cyanobenzyl bromide Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-bromo-2-(bromomethyl)benzonitrile from 5-bromo-2-methylbenzonitrile: 5-bromo-2-methylbenzonitrile (10.0 g, 51.01 mmol), N-bromosuccinimide (NBS, 9.99 g, 56.11 mmol) and benzoyl peroxide (BPO, 0.62 g, 2.6 mmol) were reacted in carbon tetrachloride ( CCl4, 100 mL) The mixture was stirred and reacted at 80 °C for 8 h under nitrogen (N2) atmosphere. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a mixed solvent of ethyl acetate/petroleum ether (gradient elution, 0-100%) to afford 5-bromo-2-(bromomethyl)benzonitrile (9.8 g, 70% yield) as a light yellow oil.1H NMR (400 MHz, CDCl3) δ 7.80 (d, J = 2.0 Hz, 1H), 7.72 (dd, J = 8.4, 2.0 Hz, 1H), 7.43 (d, J = 8.4 Hz, 1H), 4.58 (s, 2H).

References

[1] Organic Letters, 2003, vol. 5, # 7, p. 1131 - 1134
[2] Journal of Materials Chemistry, 2011, vol. 21, # 26, p. 9523 - 9531
[3] Patent: US2017/362228, 2017, A1. Location in patent: Paragraph 0464; 0465
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 2, p. 120 - 124
[5] Patent: US2016/376283, 2016, A1. Location in patent: Paragraph 0341; 0342

4-Bromo-2-cyanobenzyl bromide(156001-53-5)Related Product Information

• Lithium hydride
• Propane
• 4-Bromo-2-cyanobenzyl bromide
• 5-BROMO-2-METHYLBENZONITRILE
• 2-Cyanobenzyl bromide