2-Fluoro-4-methylbenzonitrile Chemical Properties

Melting point:

52-53°C

Boiling point:

219.6±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 Orange to Green

Water Solubility 

Insoluble in water, soluble in chloroform, acetone and other organic solvents.

InChI

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

InChIKey

WCGNLBCJPBKXCN-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(C)C=C1F

CAS DataBase Reference

85070-67-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

37/38-41-36/37/38-20/21/22

Safety Statements 

26-39-36/37-9

RIDADR 

UN3439

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

2-Fluoro-4-methylbenzonitrile Usage And Synthesis

Chemical Properties

Off white crystalline

Uses

2-Fluoro-4-methylbenzonitrile is used in the synthesis of fluorobenzamidrazone thrombin inhibitors.

Synthesis

Example 59 Preparation of 2-fluoro-4-methylbenzonitrile: 3-fluoro-4-bromotoluene (70 g, 370 mmol) and cuprous cyanide (50 g, 555 mmol) were dissolved in N,N-dimethylformamide (300 mL), heated to reflux and maintained for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature, followed by the addition of concentrated ammonia (300 mL) and ether (200 mL) with continuous stirring for 1 hour. The reaction mixture was extracted with ether (3 x 200 mL). All organic phases were combined and washed sequentially with saturated saline (3 x 200 mL) and dried over anhydrous sodium sulfate. Finally, the solvent was removed by distillation under reduced pressure to afford the light yellow solid product 2-fluoro-4-methylbenzonitrile (44 g, 88% yield). Mass spectrometry analysis showed a molecular ion peak (M + H)+ of 136.

References

[1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 9, p. 1339 - 1352
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2925 - 2930
[3] Patent: WO2007/76092, 2007, A2. Location in patent: Page/Page column 74
[4] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 7, p. 1135 - 1139
[5] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 7, p. 1439 - 1444

2-Fluoro-4-methylbenzonitrile(85070-67-3)Related Product Information

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