19639-02-2

Basic information

• Product Name: 3-butyl-5-methyldihydrofuran-2(3H)-one
• Synonyms: 2(3H)-Furanone, 3-butyldihydro-5-methyl-
• CAS NO: 19639-02-2
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.2221
• Mol File: 19639-02-2.mol

Chemical Properties

• Boiling Point: 246.5°C at 760 mmHg
• Flash Point: 95.6°C
• Density: 0.936g/cm³
• Vapor Pressure: 0.027mmHg at 25°C
• Refractive Index: 1.434
• CAS DataBase Reference: 3-butyl-5-methyldihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-butyl-5-methyldihydrofuran-2(3H)-one(19639-02-2)
• EPA Substance Registry System: 3-butyl-5-methyldihydrofuran-2(3H)-one(19639-02-2)

Safety Data

• Hazardous Substances Data: 19639-02-2(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 693-02-7 hex-1-yne 
• 74-88-4 methyl iodide 
• 94124-51-3 2-butyl-pent-4-enoic acid ethyl ester 
• 107-92-6 butyric acid 

Relevant articles and documents

Enantioselective, Catalytic One-Pot Synthesis of γ-Butyrolactone-Based Fragrances

Herein the preparative (1 g scale), stereoselective syntheses of various alkyl-substituted γ-butyrolactone fragrances 1 is described. The α,β-unsaturated γ-keto esters 2 as starting materials were synthesized by a Horner-Wadsworth-Emmons reaction and are further reduced by an ene reductase and alcohol dehydrogenase in a one-pot enzyme cascade to nine desired γ-butyrolactones 1, among them whisky (1 c) and cognac lactone (1 d). The products 1 were obtained in moderate to good yields and very good diastereoselectivities. Furthermore, the position of a nBu-substituent was permutated to study the effect on the enzyme cascade.

Economical, Green, and Safe Route Towards Substituted Lactones by Anodic Generation of Oxycarbonyl Radicals

A new electrochemical methodology has been developed for the generation of oxycarbonyl radicals under mild and green conditions from readily available hemioxalate salts. Mono- and multi-functionalised γ-butyrolactones were synthesised through exo-cyclisation of these oxycarbonyl radicals with an alkene, followed by the sp3–sp3 capture of the newly formed carbon-centred radical. The synthesis of functionalised valerolactone derivatives was also achieved, demonstrating the versatility of the newly developed methodology. This represents a viable synthetic route towards pharmaceutically important fragments and further demonstrates the practicality of electrosynthesis as a green and economical method to activate small organic molecules.

A convenient method for lactonization of α-allyl esters using iodine in dimethylsulphoxide

A simple method for the synthesis of α-γ-disubstituted-γ-butyrolactones by cyclization of α-allyl esters using iodine in dimethylsulphoxide is reported. This method is efficient and operationally simple in comparison to methods using transition metal comp

Phase-Transfer-Catalyzed Conversion of Alkynes to Lactones Induced by Manganase Carbonyl Complexes

Alkynes react with methyl iodide, bromopentacarbonylmanganese (or dimanganese decacarbonyl), and carbon monoxide, under phase-transfer catalysis conditions, to give γ-butyrolactones; the reaction conditions are mild , and the process is a regiospecific one