Cyclopentanecarboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.020.245
EC Number
  • 222-269-5
UNII
  • InChI=1S/C6H10O2/c7-6(8)5-3-1-2-4-5/h5H,1-4H2,(H,7,8)
    Key: JBDSSBMEKXHSJF-UHFFFAOYSA-N
  • C1CCC(C1)C(=O)O
Properties
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:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
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

  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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