3-CYANO-4-FLUOROBENZYL BROMIDE Chemical Properties

Boiling point:

272.7±25.0 °C(Predicted)

Density 

1.59±0.1 g/cm3(Predicted)

storage temp. 

Storage temp. 2-8°C

form 

fused solid

color 

White to off-white to faint yellow

Sensitive 

Lachrymatory

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

22

Hazard Note 

Corrosive/Lachrymatory

HS Code 

2926907090

3-CYANO-4-FLUOROBENZYL BROMIDE Usage And Synthesis

Uses

3-CYANO-4-FLUOROBENZYL BROMIDE is used in the synthetic preparations of thrombin inhibitors.

Synthesis

General procedure for the synthesis of 2-fluoro-5-(bromomethyl)benzonitrile from 2-fluoro-5-methylbenzonitrile: 2-fluoro-5-methylbenzonitrile (3.00 g, 22 mmol), N-bromosuccinimide (4.12 g, 23 mmol), and benzoyl peroxide (1.07 g, 4.4 mmol) were dissolved in carbon tetrachloride (100 mL) and heated to reflux for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently mixed with water. The organic phase was separated, dried with anhydrous magnesium sulfate and filtered through diatomaceous earth (Celite?). The filtrate was concentrated under reduced pressure and purified by fast column chromatography (n-hexane/ethyl acetate, 20:1) to afford 5-(bromomethyl)-2-fluorobenzonitrile (1.58 g, 33% yield) as an oil.1H NMR (CDCl3, 400 MHz) data were as follows: δ 4.45 (s, 2H), 7.21 (m, 1H), 7.65 (m, 2H).

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 20, p. 9422 - 9430
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2925 - 2930
[3] Helvetica Chimica Acta, 2017, vol. 100, # 12,
[4] Patent: WO2010/93845, 2010, A1. Location in patent: Page/Page column 86
[5] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 7, p. 715 - 720

3-CYANO-4-FLUOROBENZYL BROMIDE(180302-35-6)Related Product Information

• 4-Fluorobenzyl bromide