4-Fluoro-2-methylbenzonitrile Chemical Properties

Melting point:

70-74 °C (lit.)

Boiling point:

214.6±20.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C8H6FN/c1-6-4-8(9)3-2-7(6)5-10/h2-4H,1H3

InChIKey

BJBXUIUJKPOZLV-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(F)C=C1C

CAS DataBase Reference

147754-12-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN3439

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich

4-Fluoro-2-methylbenzonitrile Usage And Synthesis

Chemical Properties

White to light yellow crystalline powder

Uses

As organic intermediate, pharmaceutical intermediate. In chemical synthesis.

Synthesis

The general procedure for the synthesis of 4-fluoro-2-methylbenzonitrile from 4-fluoro-2-methylbenzenemethanol was as follows: in a 25 mL Schlenk tube equipped with a magnetic stirrer, CuCl (0.05 mmol, 5 mol%), DABCO (0.10 mmol, 10 mol%) and 4-HO-TEMPO (0.05 mmol, 5 mol%). Subsequently, a solution of acetonitrile (2 mL) with 4-fluoro-2-methylbenzenemethanol (1 mmol) and an aqueous ammonia solution (25-28%, 3 mmol, 3.0 equiv) was added. The reaction mixture was stirred at room temperature under argon protection for 24 h. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate. The organic layers were combined and dried with anhydrous magnesium sulfate. Subsequently, the organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography to afford the target product 4-fluoro-2-methylbenzonitrile.

References

[1] Organic Letters, 2013, vol. 15, # 8, p. 1850 - 1853
[2] Chinese Chemical Letters, 2018, vol. 29, # 3, p. 464 - 466

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