ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE Chemical Properties

Boiling point:

217 °C (lit.)

Density 

1.077 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.445(lit.)

Flash point:

211 °F

storage temp. 

Sealed in dry,Room Temperature

form 

liquid

color 

colorless

InChI

InChI=1S/C7H9NO2/c1-2-10-6(9)7(5-8)3-4-7/h2-4H2,1H3

InChIKey

FDZLCIITHLSEQK-UHFFFAOYSA-N

SMILES

C1(C#N)(C(OCC)=O)CC1

CAS DataBase Reference

1558-81-2(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich

ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE Usage And Synthesis

Uses

Ethyl 1-cyano-1-cyclopropanecarboxylate may be used as a monomer in the preparation of poly(ethyl trimethylene-1-cyano-1-carboxylate)s.

General Description

Ethyl 1-cyano-1-cyclopropanecarboxylate (ethyl 1-cyanocyclopropanecarboxylate) is an alkyl 1-cyanocyclopanecarboxylate. It can be prepared by reacting ethyl cyanoacetate, 1,2-dibromoethane, potassium carbonate and DMSO.

Synthesis

The general procedure for the synthesis of ethyl 1-cyanocyclopropanecarboxylate from 1,2-dibromoethane and ethyl cyanoacetate was as follows: a suspension of ethyl cyanoacetate (11.3 g, 0.1 mol), 1,2-dibromoethane, tetrabutylammonium bromide (Na 4 (n-Bu)4Br) and potassium carbonate (K 2 CO 3 ) in N,N-dimethylformamide (DMF, 100 mL) was heated to 80 °C and reacted overnight. Upon completion of the reaction, the mixture was poured into water (600 mL) and extracted with ethyl acetate (EtOAc, 3 x 50 mL). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate (Na 2 SO 4 ) and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1) to afford ethyl 1-cyanocyclopropanecarboxylate (10 g, yield: 72%).1H NMR (CDCl3, 400 MHz): δ 4.21 (q, J = 7.2 Hz, 2H), 1.65-1.61 (m, 2H), 1.58-1.55 (m, 2H) , 1.28 (t, J = 7.2 Hz, 3H).

References

[1] Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 474 - 480
[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 541 - 548
[3] Synthetic Communications, 1996, vol. 26, # 3, p. 525 - 530
[4] Tetrahedron Letters, 2005, vol. 46, # 4, p. 635 - 638
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 420 - 422

ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE(1558-81-2)Related Product Information

• Methyl cyanoacetate
• Ethyl cyanoacetate
• Ethyl 2-cyanopropanoate
• 1-METHYLCYCLOPROPANE-1-CARBOXYLIC ACID METHYL ESTER
• 1-Methylcyclopropanemethanol
• Cyclopropanecarboxylic acid
• 3-Methoxypropionitrile
• 3-Ethoxypropionitrile
• Trimethylacetonitrile
• Cyanoacetic acid
• Ethyl cyclopropanecarboxylate
• ETHYL 1-METHYLCYCLOPROPANE-1-CARBOXYLATE
• Methyl cyclopropane carboxylate
• ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE
• Cyclopropanecarbonitrile
• 1-Cyano-1-cyclopropanecarboxylic acid
• ETHYL 2-CYANOBUTANOATE
• 2-cyano-2-methylpropanoic acid