Cyclopentanecarboxylic acid

Cyclopentanecarboxylic acid
Identifiers
CAS Number	3400-45-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1902018;
ChemSpider	17789;
ECHA InfoCard	100.020.245
EC Number	222-269-5;
PubChem CID	18840;
UNII	Z6691VH94A;
CompTox Dashboard (EPA)	DTXSID70187610 ;
	InChI InChI=1S/C6H10O2/c7-6(8)5-3-1-2-4-5/h5H,1-4H2,(H,7,8) Key: JBDSSBMEKXHSJF-UHFFFAOYSA-N;
	SMILES C1CCC(C1)C(=O)O;
Properties
Chemical formula	C6H10O2
Molar mass	114.144 g·mol−1
Appearance	colorless oil
Density	1.0510 g/cm3
Melting point	−7 °C (19 °F; 266 K)
Boiling point	212 °C (414 °F; 485 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclopentanecarboxylic acid is an organic compound with the formula C₅H₉CO₂H. It is a colorless nonvolatile oil. It can be produced by the palladium-catalyzed hydrocarboxylation of cyclopentene:^[2]

C₅H₈ + CO + H₂O → C₅H₉CO₂H

An alternative route involves base-induced ring contraction of 2-chlorocyclohexanone to give the ester methyl cyclopentanecarboxylate, which can be hydrolyzed to the carboxylic acid.^[3]

References

^ "Cyclopentanecarboxylic acid". pubchem.ncbi.nlm.nih.gov.
^ Sang, Rui; Kucmierczyk, Peter; Dühren, Ricarda; Razzaq, Rauf; Dong, Kaiwu; Liu, Jie; Franke, Robert; Jackstell, Ralf; Beller, Matthias (2019). "Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation". Angewandte Chemie International Edition. 58 (40): 14365–14373. doi:10.1002/anie.201908451. PMID 31390131. S2CID 199466915.
^ D. W. Goheen, W. R. Vaughan (1959). "Methyl Cyclopentanecarboxylate". Organic Syntheses. 39: 37. doi:10.15227/orgsyn.039.0037.

[1] "Cyclopentanecarboxylic acid". pubchem.ncbi.nlm.nih.gov.

[2] Sang, Rui; Kucmierczyk, Peter; Dühren, Ricarda; Razzaq, Rauf; Dong, Kaiwu; Liu, Jie; Franke, Robert; Jackstell, Ralf; Beller, Matthias (2019). "Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation". Angewandte Chemie International Edition. 58 (40): 14365–14373. doi:10.1002/anie.201908451. PMID 31390131. S2CID 199466915.

[3] D. W. Goheen, W. R. Vaughan (1959). "Methyl Cyclopentanecarboxylate". Organic Syntheses. 39: 37. doi:10.15227/orgsyn.039.0037.

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