1-Phenyl-1-cyclohexanecarbonitrile Chemical Properties

Boiling point:

141°C/7mmHg(lit.)

Density 

1.01

refractive index 

1.5332-1.5352

Flash point:

121°

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C13H15N/c14-11-13(9-5-2-6-10-13)12-7-3-1-4-8-12/h1,3-4,7-8H,2,5-6,9-10H2

InChIKey

AUXIEQKHXAYAHG-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC=C2)(C#N)CCCCC1

NIST Chemistry Reference

1-Phenyl-1-cyclohexanecarbonitrile(2201-23-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

36/37/39-26

RIDADR 

UN 3276 6.1/PG III

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269095

MSDS

• Language:English Provider:1-Phenylcyclohexane-1-carbonitrile
• Language:English Provider:ACROS

1-Phenyl-1-cyclohexanecarbonitrile Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO PALE BROWN LIQUID

Synthesis

GENERAL STEPS: A mixture of benzeneacetonitrile (50.0 g, 426.8 mmol) and 1,5-dibromopentane (58.1 mL, 426.8 mmol) was added slowly and dropwise to a dimethylsulfoxide (600.0 mL) suspension of NaH (42.7 g, 1067.0 mmol, 60%) at 0 °C. The mixture was pre-dissolved in a solvent mixture of dimethyl sulfoxide and ether (1:1, 200.0 mL). After dropwise addition, the reaction mixture was continued to be stirred at 0°C for 2 hours. Upon completion of the reaction, water and 10% HCl solution were added to the mixture, followed by extraction with ethyl acetate. The organic layers were combined, washed sequentially with water and brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by conventional silica gel column chromatography (eluent: hexane) to afford 1-phenyl-1-cyclohexanecarbonitrile (52.0 g, yield 65.76%) as a colorless oil.GC-MS analysis showed that the molecular ion peak m/z was 185.0.

References

[1] Patent: US2014/194431, 2014, A1. Location in patent: Paragraph 0940-0942
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3913 - 3924
[3] Journal of Organic Chemistry, 1971, vol. 36, p. 1308 - 1309
[4] Chemische Berichte, 1973, vol. 106, p. 2890 - 2903
[5] Bulletin de la Societe Chimique de France, 1965, p. 2030 - 2037

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