1-Cyano-1-cyclopropanecarboxylic acid Chemical Properties

Melting point:

140 °C (lit.)

Boiling point:

142 °C

Density 

1.3113 (rough estimate)

refractive index 

1.4260 (estimate)

storage temp. 

2-8°C

pka

2.31±0.20(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

6914-79-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

20/21/22-34

Safety Statements 

26-27-36/37/39-45-25

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29269090

MSDS

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

1-Cyano-1-cyclopropanecarboxylic acid Usage And Synthesis

Chemical Properties

white to light brown crystalline powder

Uses

1-Cyano-1-cyclopropanecarboxylic acid may be used in the synthesis of amidine-based nanomolar sphingosine kinase1 subtype-selective inhibitors.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 2969, 1975 DOI: 10.1021/jo00908a030

General Description

1-Cyano-1-cyclopropanecarboxylic acid (1-Cyanocyclopropanecarboxylic acid) is a substituted cyclopropane. It is the intermediate formed during homoconjugate addition of nucleophiles to cyclopropane-1,1-dicarboxylate derivative.

Synthesis

General procedure for the synthesis of 1-cyano-1-cyclopropanecarboxylic acid from methyl 1-cyanocyclopropanecarboxylate: KOH (13.78 g, 85%, 209 mmol) was dissolved in 80 mL of ethanol, and then this solution was added to a 100 mL ethanol solution of methyl 1-cyano-1-cyclopropanecarboxylate (25.64 g, 205 mmol), and the reaction was stirred for 1 hour. After completion of the reaction, the mixture was evaporated and concentrated, dissolved in 200 mL of water and the aqueous phase was washed with 30 mL of chloroform. Subsequently, the aqueous phase was acidified with hydrochloric acid to pH=1. 30 g of NaCl was added to the acidified mixture, followed by 6 extractions with 50 mL of chloroform. All organic layers were combined, dried with anhydrous MgSO4 and finally the solvent was evaporated under vacuum to afford the target product 1-cyano-1-cyclopropanecarboxylic acid (20.60 g, 90% yield). The product was characterized by 1H NMR (200 MHz, DMSO-d6): δ 1.73 (m, 4H), 11.08 (s, 1H).

References

[1] Tetrahedron, 2013, vol. 69, # 16, p. 3495 - 3505

1-Cyano-1-cyclopropanecarboxylic acid(6914-79-0)Related Product Information

• Cyclopropane
• Sodium cyanoborohydride
• Cyclopropanecarbonitrile
• Ethyl isocyanoacetate
• 1-Aminocyclopropanecarboxylic acid
• Cyclopropanecarboxylic acid
• Cyclopropyl bromide
• Folic acid
• 1,1-Bis(hydroxymethyl)cyclopropane
• ETHYL 2-CYANOACRYLATE
• Ethyl 2-(Chlorosulfonyl)acetate
• Methylene dithiocyanate
• Ascoric Acid
• ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE
• Ethyleneimine
• 1-CYANO-CYCLOPROPANECARBOXYLIC ACIDMETHYL ESTER
• aminocyclopropane-1-carboxylic acid
• 1-Cyano-1-cyclopropanecarboxylic acid