Cyclopropane carboxylic acid

Last updated
Cyclopropane carboxylic acid
C3H5CO2H.svg
Identifiers
3D model (JSmol)
969839
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.015.602 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 217-162-5
2246
KEGG
PubChem CID
UNII
  • InChI=1S/C4H6O2/c5-4(6)3-1-2-3/h3H,1-2H2,(H,5,6)
    Key: YMGUBTXCNDTFJI-UHFFFAOYSA-N
  • C1CC1C(=O)O
Properties
C4H6O2
Molar mass 86.090 g·mol−1
Appearancecolorless oil
Density 1.0829 g/cm3
Melting point 18.5 °C (65.3 °F; 291.6 K)
Boiling point 76 °C (169 °F; 349 K) 12 Torr
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H314
P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclopropane carboxylic acid is the organic compound with the formula C3H5CO2H. It is the carboxylic acid derivative of cyclopropane. It can be prepared by hydrolysis of cyanocyclopropane, which is obtained by base-induced cyclization of 4-chlorobutyronitrile. [1]

Reactions

Cyclopropane carboxylic acid has al pKa of 4.65, fairly typical for similar compounds. [2] Esterification is conveniently done with Lewis acid catalysts. [3]

The compound has been used to probe the biosynthesis of ethylene. [4]

References

  1. Chester M. McCloskey, George H. Coleman (1944). "Cyclopropanecarboxylic Acid". Organic Syntheses. 24: 36. doi:10.15227/orgsyn.024.0036.
  2. Wiberg, Kenneth B.; Ross, Brenda S.; Isbell, John J.; McMurdie, Neil (1993). "2-Substituted Bicyclo[1.1.1]pentanes". The Journal of Organic Chemistry. 58 (6): 1372–1376. doi:10.1021/jo00058a015.
  3. Ishihara, Kazuaki; Nakayama, Masaya; Ohara, Suguru; Yamamoto, Hisashi (2002). "Direct Ester Condensation from a 1:1 Mixture of Carboxylic Acids and Alcohols Catalyzed by Hafnium(IV) or Zirconium(IV) Salts". Tetrahedron. 58 (41): 8179–8188. doi:10.1016/s0040-4020(02)00966-3.
  4. Tian, Qiu-Ying; Sun, Pei; Zhang, Wen-Hao (2009). "Ethylene is Involved in Nitrate-Dependent Root Growth and Branching in Arabidopsis thaliana". New Phytologist. 184 (4): 918–931. Bibcode:2009NewPh.184..918T. doi:10.1111/j.1469-8137.2009.03004.x. PMID   19732351.