13679-56-6

Basic information

• Product Name: 4-(5-Methyl-2-furyl)butan-2-one
• Synonyms: 4-(5-Methyl-2-furyl)butan-2-one;4-(5-METHYL-2-FURYL)-2-BUTANONE;2-Methyl-5-(3-oxobutyl)furan;4-(5-Methyl-2-furanyl)-2-butanone;4-(5-Methylfuran-2-yl)-2-butanone
• CAS NO: 13679-56-6
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19038
• Mol File: 13679-56-6.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 209.6°Cat760mmHg
• Flash Point: 87.1°C
• Appearance: /
• Density: 1.004g/cm³
• Vapor Pressure: 0.201mmHg at 25°C
• Refractive Index: 1.469
• CAS DataBase Reference: 4-(5-Methyl-2-furyl)butan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-Methyl-2-furyl)butan-2-one(13679-56-6)
• EPA Substance Registry System: 4-(5-Methyl-2-furyl)butan-2-one(13679-56-6)

Safety Data

• Hazardous Substances Data: 13679-56-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 4183, 1991 DOI: 10.1016/S0040-4039(00)79899-6

InChI:InChI=1/C9H12O2/c1-7(10)3-5-9-6-4-8(2)11-9/h4,6H,3,5H2,1-2H3

Upstream product

• 534-22-5 2-methylfuran 
• 78-94-4 methyl vinyl ketone 
• 66434-99-9 (E)-4-(5-Methyl-furan-2-yl)-but-3-en-2-one 
• 67935-23-3 trans-3-methoxybut-2-en-1-ol 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 554-14-3 2-Methylthiophene 
• 598-32-3 2-hydroxy-3-butene 
• 23120-57-2 4-(5-methyl-2-furanyl)-3-buten-2-one 
• 1245713-17-0 4-(5-hydroxy methyl)-2-furanyl-2-butanone 
• 888014-45-7 3-(hydroxymethyl)-2-furaldehyde 
• 620-02-0 5-Methylfurfural 

Downstream Products

• 30502-73-9 2,8-nonanedione 
• 25234-82-6 nonane-2,5-dione 
• 38284-28-5 nonane-2,5,8-trione 
• 67137-66-0 4-(5-methylthiophene-2-yl)butan-2-one 
• 111-84-2 nonane 

Relevant articles and documents

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in water: Synthesis of DE-bicycles of the pectenotoxins

Photooxygenations of 2-(γ,ε-dihydroxyalkyl) furans in H 2O followed by in situ reduction and ketalization affords, in one synthetic operation, DE-bicyclic ketals of the pectenotoxins.

Effect of water on chemo- and endo-selectivity in high pressure Diels-Alder furan reactions. Hydrophobic or polar effects?

Diels-Alder furan additions are less sensitive to pressure in aqueous solution than in organic solvents. In some cases, water affects chemo- and stereoselectivity. The interpretation takes into account hydrophobic as well as polar effects induced by water.

CHEMOSELECTIVE REDUCTION IN CARBONYL-CONJUGATED VINYLFURANS BY THE Mg/MeOH SYSTEM

Chemoselective reduction of double bonds conjugated with carbonyl groups and furan rings has been accomplished by using Mg/MeOH reducing system.

Michael Additions Catalyzed by a β-Diketiminate-Supported Aluminum Complex

A β-diketiminate-supported aluminum bistriflate complex (DipLAl(OTf)2·Na[BArCl4]; DipL = CH(CMe)2(N-C6H3-iPr2)2; Tf = O2SCF

Copper(II) bromide-catalyzed conjugate addition of furans to α,β-unsaturated carbonyl compounds

[Figure not available: see fulltext.] A simple method for the synthesis of 2-(3-oxoalkyl)furan derivatives based on conjugate addition of 2-substituted furans to various α,β-unsaturated carbonyl compounds in the presence of copper(II) bromide as catalyst was developed.

Synthesis of Renewable Triketones, Diketones, and Jet-Fuel Range Cycloalkanes with 5-Hydroxymethylfurfural and Ketones

A series of renewable C9–C12triketones with repeating [COCH2CH2] units were synthesized in high carbon yields (ca. 90 %) by the aqueous-phase hydrogenation of the aldol-condensation products of 5-hydroxylmethylfurfural (HMF) and ketones over an Au/TiO2catalyst. Compared with the reported routes, this new route has many advantages such as being environmentally friendly, having fewer steps, using a cheaper and reusable catalyst, etc. The triketones as obtained can be used as feedstocks in the production of conducting or semi-conducting polymers. Through a solvent-free intramolecular aldol condensation over solid-base catalysts, the triketones were selectively converted to diketones, which can be used as intermediates in the synthesis of useful chemicals or polymers. As another application, the tri- and diketones can also be utilized as precursors for the synthesis of jet-fuel range branched cycloalkanes with low freezing points (224–248 K) and high densities (ca. 0.81 g mL?1).