2-BROMO-4-METHYLBENZONITRILE Chemical Properties

Melting point:

51-53°C

Boiling point:

110°C/5mm

Density 

1.51±0.1 g/cm3(Predicted)

Flash point:

110 °C

storage temp. 

Inert atmosphere,Room Temperature

form 

powder

Appearance

White to off-white Solid

InChI

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

InChIKey

JWCMJJIZYDCGTE-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(C)C=C1Br

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39

RIDADR 

3439

WGK Germany 

3

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

2926907090

2-BROMO-4-METHYLBENZONITRILE Usage And Synthesis

Chemical Properties

off-white crystalline

Uses

3-Bromo-4-cyanotoluene reacts with magnesium to form Grignard reagent, which can be used as a catalyst for the polymerization of acetylene.

Synthesis

Example 10 Synthesis of 2-bromo-4-methylbenzonitrile: To a chloroform suspension of 2-bromo-4-methylbenzamide (14.8 g, 69.1 mmol) was added phosphorus pentoxide (24.5 g, 172.8 mmol), and the reaction mixture was refluxed for 12 hours. After completion of the reaction, it was cooled to room temperature and slowly poured into ice water with stirring. The organic layer was separated and the aqueous layer was extracted twice with chloroform (150 mL x 2). The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 2-bromo-4-methylbenzonitrile (13.3 g, 98% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 2.41 (s, 3H), 7.20 (d, J=8.0 Hz, 1H), 7.51-7.54 (m, 2H).

References

[1] Patent: US2009/203657, 2009, A1. Location in patent: Page/Page column 45
[2] Patent: US2009/203677, 2009, A1. Location in patent: Page/Page column 48
[3] Patent: US2009/197871, 2009, A1. Location in patent: Page/Page column 47-48
[4] Patent: WO2009/100169, 2009, A1. Location in patent: Page/Page column 122
[5] Patent: WO2007/68905, 2007, A1. Location in patent: Page/Page column 128

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