3-Bromo-4-methylbenzonitrile Chemical Properties

Melting point:

41-45 °C (lit.)

Boiling point:

259.1±20.0 °C(Predicted)

Density 

1.51±0.1 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

fused solid

Appearance

White to off-white Solid

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C8H6BrN/c1-6-2-3-7(5-10)4-8(6)9/h2-4H,1H3

InChIKey

VXUMRYMTYKDWMO-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

42872-74-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22

Safety Statements 

36

RIDADR 

UN3439

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

2926907090

3-Bromo-4-methylbenzonitrile Usage And Synthesis

Chemical Properties

Off-white crystalline

Uses

Used as pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 3-bromo-4-methylbenzonitrile from 4-methylbenzonitrile: 4-methylbenzonitrile (168 g, 1.46 mol) was dissolved in a mixed solution of H2SO4/H2O (800 mL, 1:1, v/v/v) at 10 °C and N-bromosuccinimide (NBS, 256 g, 1.43 mol) was added slowly. The reaction mixture was stirred under light-avoiding conditions for 48 hours. After completion of the reaction, the mixture was filtered and the filter cake was collected. The filter cake was dissolved in ethyl acetate (1000 mL) and the organic layer was washed sequentially with water and saturated saline. Subsequently, it was neutralized with NaOH solution to pH=7 and washed again with saturated saline. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 3-bromo-4-methylbenzonitrile (276.5 g, 89% yield) as a yellow solid.

References

[1] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 2, p. 217 - 223
[2] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 2, p. 248 - 255
[3] Patent: WO2011/22337, 2011, A1. Location in patent: Page/Page column 103-104
[4] Synlett, 2007, # 14, p. 2179 - 2184
[5] Organic Letters, 2006, vol. 8, # 4, p. 645 - 647

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