Cyclopropane carboxylic acid

Cyclopropane carboxylic acid
Identifiers
CAS Number	1759-53-1;
3D model (JSmol)	Interactive image;
Beilstein Reference	969839
ChEBI	CHEBI:23500;
ChEMBL	ChEMBL4649900;
ChemSpider	14890;
ECHA InfoCard	100.015.602
EC Number	217-162-5;
Gmelin Reference	2246
KEGG	C16267;
PubChem CID	15655;
UNII	008803351S;
CompTox Dashboard (EPA)	DTXSID1040665 ;
	InChI InChI=1S/C4H6O2/c5-4(6)3-1-2-3/h3H,1-2H2,(H,5,6) Key: YMGUBTXCNDTFJI-UHFFFAOYSA-N;
	SMILES C1CC1C(=O)O;
Properties
Chemical formula	C4H6O2
Molar mass	86.090 g·mol−1
Appearance	colorless 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:[1]
Pictograms
Signal word	Danger
Hazard statements	H302, H314
Precautionary statements	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). Infobox references

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

^ Chester M. McCloskey, George H. Coleman (1944). "Cyclopropanecarboxylic Acid". Organic Syntheses. 24: 36. doi:10.15227/orgsyn.024.0036.
^ 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.
^ 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.
^ 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.

[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.

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