934-42-9

Basic information

• Product Name: 2-butylcyclopentanone
• Synonyms: 2-butylcyclopentanone;2-Butyl-1-cyclopentanone;2-butylcyclopentan-1-one
• CAS NO: 934-42-9
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22274
• EINECS: 213-282-7
• Mol File: 934-42-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 200.1 °C at 760 mmHg
• Flash Point: 67.7 °C
• Appearance: /
• Density: 0.9 g/cm³
• Vapor Pressure: 0.33mmHg at 25°C
• Refractive Index: 1.448
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-butylcyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-butylcyclopentanone(934-42-9)
• EPA Substance Registry System: 2-butylcyclopentanone(934-42-9)

Safety Data

• Hazardous Substances Data: 934-42-9(Hazardous Substances Data)

Usage

General Description

2-butylcyclopentanone is a chemical compound with the molecular formula C11H20O. It is a cyclic ketone with a butyl group attached to the cyclopentane ring. 2-butylcyclopentanone is commonly used as a flavoring agent in food products and as a fragrance in perfumes and personal care products due to its pleasant and fruity odor. It is also used in the manufacture of pharmaceuticals and other organic compounds. 2-butylcyclopentanone is a colorless liquid at room temperature and is considered to be relatively stable under normal conditions. Its chemical structure and properties make it a versatile and valuable ingredient in various industrial applications.

InChI:InChI=1/C9H16O/c1-2-3-5-8-6-4-7-9(8)10/h8H,2-7H2,1H3

Upstream product

• 16424-32-1 2-Buthylidenecyclopentenone 
• 109-65-9 1-bromo-butane 
• 62803-93-4 2-(1-Butenyl)-2-cyclopentenon 
• 56292-34-3 2-Butylidencyclopentanol 
• 14090-60-9 2-cyclopentylidene-1,1-dimethylhydrazine 
• 5561-05-7 2-butylcyclopent-2-enone 
• 120-92-3 cyclopentanone 
• 1056246-36-6 2-bromocyclopentanone 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 85706-66-7 (E)-2-(cyclopropylmethylene)cyclopentanone 
• 81465-61-4 (E)-2-(iodomethylene)cyclopentanone 
• 42908-34-9 N-cyclohexyl-N-cyclopentylidenamine 
• 33948-35-5 2-iodo-cyclopent-2-enone 
• 930-30-3 cyclopent-2-enone 

Downstream Products

• 1497405-14-7 (3aS,8bS)-4-benzyl-8b-butyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole 
• 1497405-24-9 C₂₂H₂₇NO 
• 1337968-21-4 C₁₁H₂₀O₂ 
• 2801-82-3 cis-1,2-dibutylcyclopentane 
• 2801-82-3 trans-1,2-dibutylcyclopentane 
• 1239335-22-8 (1R,2S)-4-methoxy-N-(2-butylcyclopentyl)aniline 
• 102707-15-3 N-(2-butyl-cyclopentyl)-N-cyclopentyl-N'-phenyl-urea 
• 3301-94-8 6-Butyl-tetrahydro-pyran-2-one 

Relevant articles and documents

Strictly regiocontrolled α-monosubstitution of cyclic carbonyl compounds with alkynyl and alkyl groups via Pd-catalyzed coupling of cyclic α-iodoenones with organozincs

The conditions for the Pd-catalyzed cross coupling of cyclic α-iodoenones, such as 2-iodo-2-cyclohexenone, with alkynylzincs have been optimized. The use of tris(o-furyl)phosphine (TFP) as a ligand and DMF as a solvent has led to the formation of α-alkynylenones in excellent yields. This optimized procedure has been applied to the synthesis of (±)-harveynone and (±)-tricholomenyn A in high yields. Investigation of related α-alkylation reactions using alkylzincs has revealed the following. Methylzinc and primary alkylzinc derivatives readily undergo Pd-catalyzed cross coupling with α-iodoenones. Although (s-Bu)2Zn also undergoes Pd-catalyzed cross coupling, only the n-Bu-substituted products were obtained, α-Benzylation and α-homobenzylation can proceed satisfactorily, whereas allylzinc and propargylzinc derivatives undergo only addition to the carbonyl group. Although some promising results have been obtained in α-homoallylation and α-homopropargylation, these reactions need to be further improved. (C) 2000 Elsevier Science Ltd.

Consecutive 6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions

A range of substituted Se-phenyl 5,9-dieneselenoates, viz. 15a, 25, 26, 27, 42 and 52, have been synthesised and their reactions with Bu3SnH-AIBN investigated.The diene esters 15a, 42 and 52 are shown to lead to decalone and to perhydrophenanthrone derivatives, viz. 19, 43 and 53, respectively, via consecutive 6-endo trig modes of cyclisations starting from the corresponding 5,9-diene acyl radical intermediates.By contrast, the 5,9-dienoates 25 and 27 lacking alkyl substitution at C-9 instead underwent cyclisation to the indanones 36 and 37, respectively, and the 6-methyl substituted analogue 26 produced only the cyclopentanone 38 on treatment with Bu3SnH-AIBN.

An Organozinc Aid in Alkylation and Acylation of Lithium Enolates

The presence of dimethylzinc in the reaction of lithium enolates and electrophiles effectively suppresses undesired α-proton exchange reaction and enhances the efficiency of enolate alkylation and acylation.