1-PHENYL-1-CYCLOPROPANECARBONITRILE Chemical Properties

Boiling point:

133-137 °C30 mm Hg(lit.)

Density 

1 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.539(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

Specific Gravity

1.000

color 

Clear colorless to slightly yellow

InChI

InChI=1S/C10H9N/c11-8-10(6-7-10)9-4-2-1-3-5-9/h1-5H,6-7H2

InChIKey

ZHFURHRJUWYDKG-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC=C2)(C#N)CC1

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36

RIDADR 

UN3276

WGK Germany 

3

HazardClass 

6.1

HS Code 

29269095

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

1-PHENYL-1-CYCLOPROPANECARBONITRILE Usage And Synthesis

Chemical Properties

Clear colorless to slightly yellow liquid

Synthesis

Step 1: Preparation of 1-phenylcyclopropanecarbonitrile To a stirred mixture of phenylacetonitrile (100 g, 0.8547 mol) dissolved in aqueous KOH (447 g, dissolved in 420 mL of water) and 2.7 g of tetrabutylammonium bromide, 1,2-dibromoethane (147 mL, 1.709 mol) was added slowly dropwise, with the rate of dropwise acceleration being controlled to maintain the temperature of the reaction at 50 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 50 °C for 1 hour. Upon completion of the reaction, the mixture was poured into cold water and extracted with diisopropyl ether. The organic phases were combined and the crude product was purified by high vacuum distillation to give 90 g of colorless liquid 1-phenylcyclopropane carbonitrile in 73% yield.

References

[1] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1775 - 1779
[2] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 10, p. 2086 - 2091
[3] Tetrahedron Letters, 2006, vol. 47, # 23, p. 3871 - 3874
[4] Patent: WO2011/61760, 2011, A1. Location in patent: Page/Page column 17-18
[5] Organic Letters, 2015, vol. 17, # 20, p. 4944 - 4947

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