Chemistry:Cyclopentanecarboxylic acid

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Cyclopentanecarboxylic acid
Cyclopentanecarboxylic acid.svg
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 222-269-5
UNII
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 pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
P261, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P271, P280, P302+352, P304+340, P305+351+338, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P332+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P403+233, 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 C
5
H
9
CO
2
H
. It is a colorless nonvolatile oil. It can be produced by the palladium-catalyzed hydrocarboxylation of cyclopentene:[2]

C
5
H
8
+ CO + H
2
O → C
5
H
9
CO
2
H

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" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/18840#section=Safety-and-Hazards. 
  2. Sang, Rui; Kucmierczyk, Peter; Dühren, Ricarda; Razzaq, Rauf; Dong, Kaiwu; Liu, Jie; Franke, Robert; Jackstell, Ralf et al. (2019). "Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation". Angewandte Chemie International Edition 58 (40): 14365–14373. doi:10.1002/anie.201908451. PMID 31390131. 
  3. D. W. Goheen, W. R. Vaughan (1959). "Methyl Cyclopentanecarboxylate". Organic Syntheses 39: 37. doi:10.15227/orgsyn.039.0037.