| Identification | Back Directory | [Name]
1-CYCLOPENTYL-ETHANONE | [CAS]
6004-60-0 | [Synonyms]
Acetylcyclopentane
CYCLOPENTYLETHANONE
1-Acetylcyclopentane
1-CYCLOPENTYL-ETHANONE
1-cyclopentylethan-1-one
ethanone, 1-cyclopentyl-
Ketone, cyclopentyl methyl
Cyclopentyl(methyl) ketone
Cyclopentylmethylketone,98%
1-cyclopentylethanone
Chemical
Ethanone, 1-cyclopentyl- (9CI)
Ketone, cyclopentyl methyl (8CI)
1-cyclopentylethanone(SALTDATA: FREE) | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C7H12O | [MDL Number]
MFCD00060799 | [MOL File]
6004-60-0.mol | [Molecular Weight]
112.17 |
| Questions And Answer | Back Directory | [Synthesis]
In a reaction flask, 1,4-dibromobutane (216 g, 1.0 mol) and 40% sodium hydride (90 g, 1.5 mol) were added, and the mixture was slowly heated to 50°C under nitrogen protection. Methyl acetoacetate (116 g, 1.0 mol) was slowly added, maintaining the temperature below 55°C. After the addition was complete, the mixture was heated and stirred at 50°C for 3 hours. The reaction was monitored by TLC until the reactants were fully reacted. Then, 1N... The pH of the reaction solution was adjusted to 8-9 with HCl solution, and the temperature was maintained at 60℃ for 2 hours. Then the temperature was lowered to 40℃. The organic phase was separated, washed once with 100 mL of saturated sodium chloride solution, dried with 5 g of anhydrous magnesium sulfate, and finally concentrated under vacuum to obtain 102 g of 1-CYCLOPENTYL-ETHANONE, with a yield of 91%. |
| Chemical Properties | Back Directory | [Melting point ]
115-116 °C(Solvent: Ethanol) | [Boiling point ]
151-156℃ | [density ]
0.913 | [refractive index ]
1.4435 | [storage temp. ]
2-8°C | [form ]
clear liquid | [color ]
Colorless to Almost colorless | [Water Solubility ]
Miscible with water. | [InChI]
InChI=1S/C7H12O/c1-6(8)7-4-2-3-5-7/h7H,2-5H2,1H3 | [InChIKey]
LKENTYLPIUIMFG-UHFFFAOYSA-N | [SMILES]
C(=O)(C1CCCC1)C | [LogP]
1.340 (est) | [NIST Chemistry Reference]
Ethanone, 1-cyclopentyl-(6004-60-0) |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless Liquid | [Uses]
Cyclopentyl methyl ketone acts as a ligand for Suzuki coupling. Further, it reacts with benzo[1,2,5]oxadiazole 1-oxide to prepare 3-methylspiro(chinoxalin-2(3H),1'-cyclopentan)-3-amin-1,4-dioxide. | [Synthesis Reference(s)]
Tetrahedron, 39, p. 3207, 1983 DOI: 10.1016/S0040-4020(01)91568-6 | [Synthesis]
The preparation of 1-cyclopentylethanone: Condensation of 1,4-dibromobutane (XII) with tert-
butylacetoacetate (XIII) using NaOH in the presence of Bu4NBr,
or K2CO3 in the presence of Bu4NI in DMSO at 50 °C gives
tert-butyl 1-acetylcyclopentanecarboxylate (XIV), which
upon hydrolysis with HCl in i-prOH at 70 °C, TFA at 65 °C
or H2SO4 at 120 °C affords 1-cyclopentylethanone (XV) [1]. The reaction pathway is shown below:
 | [References]
[1] Tanturovska, B. S., Huwiler, A. (2020). Cenerimod. Sphingosine 1-phosphate receptor 1 (S1P1) agonist, Treatment of systemic lupus erythematosus. Drugs of The Future, 1 1. https://doi.org/10.1358/dof.2020.45.11.3176881 |
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