2-Fluoro-4-cyanobenzyl bromide Chemical Properties

Melting point:

77 °C

Boiling point:

276.4±30.0 °C(Predicted)

Density 

1.59±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Solid

color 

Off-white

Sensitive 

Lachrymatory

InChI

InChI=1S/C8H5BrFN/c9-4-7-2-1-6(5-11)3-8(7)10/h1-3H,4H2

InChIKey

ZESZAIOGACKOMB-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(CBr)C(F)=C1

CAS DataBase Reference

105942-09-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

RIDADR 

3439

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

8

PackingGroup 

III

HS Code 

29269090

2-Fluoro-4-cyanobenzyl bromide Usage And Synthesis

Chemical Properties

White to yellow fine crystalline powder

Uses

2-Fluoro-4-cyanobenzyl bromide can be used in organic synthesis.

Synthesis

General procedure for the synthesis of 4-cyano-2-fluorobenzyl bromide from 3-fluoro-4-methylbenzonitrile: 3-fluoro-4-methylbenzonitrile (40 g, 296 mmol), N-bromosuccinimide (NBS, 63.2 g, 356 mmol), and benzoyl peroxide (3.6 g, 14.8 mmol) were dissolved in carbon tetrachloride (490 mL), and the reaction was performed at reflux for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated and purified by fast column chromatography (eluent: 0-5% ethyl acetate/hexane) to afford the target product 4-(bromomethyl)-3-fluorobenzonitrile (35.4 g, 56% yield).

References

[1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 12, p. 1647 - 1650
[2] Organic and Biomolecular Chemistry, 2004, vol. 2, # 9, p. 1339 - 1352
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 12, p. 1203 - 1207
[4] Patent: WO2016/109361, 2016, A2. Location in patent: Paragraph 00144
[5] Patent: US2010/240719, 2010, A1. Location in patent: Page/Page column 11

2-Fluoro-4-cyanobenzyl bromide(105942-09-4)Related Product Information

• alpha-Chloro-o-fluorotoluene
• Ethidium bromide
• BENDROFLUMETHIAZIDE
• Vecuronium bromide
• Ethyl bromodifluoroacetate
• Allyl bromide
• Rocuronium bromide
• Sodium bromate
• Dimidium bromide
• Bromofluoromethane
• Benzyl bromide
• Fluorine
• 3-CYANO-4-FLUOROBENZYL BROMIDE
• 4-Cyanobenzyl bromide
• 2-FLUORO-4-METHYLBENZYL BROMIDE
• Methyl bromide
• 2-Fluorobenzyl bromide
• 4-Nitrobenzyl bromide