63759-55-7

Basic information

• Product Name: 3-methyleneoctan-2-one
• Synonyms: 3-methyleneoctan-2-one;2-Octanone, 3-methylene-;2-PENTYL-1-BUTEN-3-ONE;3-METHYLIDENEOCTAN-2-ONE;3-Methylene-2-octanone
• CAS NO: 63759-55-7
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22274
• EINECS: 264-448-0
• Mol File: 63759-55-7.mol

Chemical Properties

• Boiling Point: 198.3°C at 760 mmHg
• Flash Point: 71.6°C
• Appearance: /
• Density: 0.829g/cm³
• Vapor Pressure: 0.361mmHg at 25°C
• Refractive Index: 1.426
• CAS DataBase Reference: 3-methyleneoctan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyleneoctan-2-one(63759-55-7)
• EPA Substance Registry System: 3-methyleneoctan-2-one(63759-55-7)

Safety Data

• Hazardous Substances Data: 63759-55-7(Hazardous Substances Data)

Usage

Chemical Properties

2-Pentyl-1-buten-3-one has a musty, mushroom odor.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 2483, 1986 DOI: 10.1016/S0040-4039(00)84562-1

InChI:InChI=1/C9H16O/c1-4-5-6-7-8(2)9(3)10/h2,4-7H2,1,3H3

Upstream product

• 111-13-7 hexyl-methyl-ketone 
• 71268-61-6 3-phenylsulfanylmethyl-octan-2-one 
• 69843-65-8 3-methoxymethyl-octan-2-one 
• 50-00-0 formaldehyd 
• 69843-64-7 trimethyl-(1-methyl-hept-1-enyloxy)-silane 
• 106729-35-5 2-Acetoxymethyl-2-acetyl-heptanoic acid allyl ester 

Relevant articles and documents

PROCESS FOR THE DIRECT ALPHA-METHYLENATION OF KETONES

The invention relates to a process for preparing an α-methylene ketone comprising the step of reacting a ketone with formaldehyde in the presence of a catalyst which is an organic compound comprising at least one acid function or the corresponding salt, ester or amide thereof and at least one amine function or the corresponding ammonium salt, or a zwitterion thereof.

α-ALKYLATION AND α-ALKYLIDENATION OF CARBONYL COMPOUNDS BY O-SILYLATED ENOLATE PHENYLTHIOALKYLATION

For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates.In the case of α-alkylation of carbonyl compounds, Lewis acid (TiCl4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, Bui, and Me3Si), followed by reductive sulphur removal by Raney nickel, 5->6, is found to be a reliable method for this synthetically important C-C bond forming step.An alternative sulphur elimination pathway via the sulphoxide, 5->7, allows the regio- and stereocontrolled α-alkylidenation of carbonyl compounds.The phenylthioalkylation reaction is applicable to ketones, aldehydes, esters, and lactones.

PREPARATION OF α-METHYLENE KETONES BY THE PALLADIUM-CATALYZED DECARBOXYLATION-DEACETOXYLATION OF ALLYL α-ACETOXYMETHYL-β-KETO CARBOXYLATES UNDER MILD CONDITIONS

α-Methylene ketones are prepared in high yields by the palladium-catalyzed decarboxylation-deacetoxylation of allyl α-acetoxymethyl-β-keto carboxylates.The reaction proceeds rapidly at room temperature under neutral conditions in acetonitrile.