4-Cyanobenzyl bromide Chemical Properties

Melting point:

115-117 °C(lit.)

Boiling point:

143 °C / 12mmHg

Density 

1.5466 (rough estimate)

refractive index 

1.6550 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless to yellow

Water Solubility 

Soluble in chloroform and methanol. Insoluble in water.

BRN 

636717

InChI

InChI=1S/C8H6BrN/c9-5-7-1-3-8(6-10)4-2-7/h1-4H,5H2

InChIKey

UMLFTCYAQPPZER-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

17201-43-3(CAS DataBase Reference)

NIST Chemistry Reference

«ALPHA»-bromo-p-tolunitrile(17201-43-3)

EPA Substance Registry System

Benzonitrile, 4-(bromomethyl)- (17201-43-3)

Safety Information

Hazard Codes 

C

Risk Statements 

34-42/43

Safety Statements 

22-26-36/37/39-45-28A

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

10-19-21

Hazard Note 

Corrosive

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29269090

MSDS

• Language:English Provider:alpha-Bromo-p-tolunitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Cyanobenzyl bromide Usage And Synthesis

Uses

4-Cyanobenzyl bromide is an important intermediate for pharmaceutical production. It can be used for the synthesis of a series of piperidine-linked aromatic diimidazolines, which have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii (PCP) drug, Pentamidine.

Chemical Properties

4-Cyanobenzyl bromide (C8H6BrN, CAS registry No. 17201-43-3) is a white solid. Its melting point is 113-117°C, and flash point is 125.1°C. It is insoluble in water at 20°C. It is stable under normal temperatures and pressures. It should be stored at 0-5°C.

Chemical Properties

white to light yellow crystal powde

Uses

A benzyl halide as postemergence herbicides.

Uses

4-(Bromomethyl)benzonitrile is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.

Uses

4-(Bromomethyl)benzonitrile may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile.

General Description

4-(Bromomethyl)benzonitrile reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile.

Synthesis

GENERAL METHOD: Hydroxymethyl (1 mmol) and potassium bromide (1.5 mmol, 0.18 g) were dissolved in ethanol (5 mL) and phosphorus pentoxide (1.5 mmol, 0.23 g) was added. The reaction mixture was stirred at room temperature until the reaction was complete (monitored by TLC or GC). After completion of the reaction, the mixture was filtered and the residue was washed with ethyl acetate (3 x 8 mL). The organic layers were combined, washed with water (10 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude 4-cyanobenzyl bromide product. If further purification is required, column chromatography can be used.

References

[1] Tetrahedron Letters, 2016, vol. 57, # 2, p. 168 - 171
[2] Organic Letters, 2015, vol. 17, # 15, p. 3810 - 3813
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 11, p. 1731 - 1735
[4] Patent: US6384080, 2002, B1

4-Cyanobenzyl bromide(17201-43-3)Related Product Information

• Methyl 4-cyanobenzoate
• 4-Cyanobenzoyl chloride
• Ethidium bromide
• 4-Cyanophenol
• Sodium bromate
• Rocuronium bromide
• ETHYL 2-CYANOACRYLATE
• Sodium cyanoborohydride
• Ethyl cyanoformate
• 2-Cyanoacetamide
• Methylene dithiocyanate
• Diethylstilbestrol
• Benzyl bromide
• Allyl bromide
• Cyanoacetic acid
• α-Lipoic Acid
• 2-Fluoro-4-cyanobenzyl bromide
• Bromine