6975-60-6

Basic information

• Product Name: 2-FURYLACETONE
• Synonyms: (Furyl-2)-1-propanone-2;1-(2-furanyl)-2-propanon;1-(2-furyl)propan-2-one;2-Furfuryl methyl ketone;Furfuryl methyl ketone;1-(2-FURYL)-2-PROPANONE;2-FURYLACETONE;2-FURYL-2-PROPANONE
• CAS NO: 6975-60-6
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• EINECS: 230-234-0
• Mol File: 6975-60-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 28-30°C
• Boiling Point: 179-180°C
• Flash Point: 179-180°C
• Appearance: /
• Density: 1.1040
• Vapor Pressure: 0.938mmHg at 25°C
• Refractive Index: 1.5035 (estimate)
• Solubility: Soluble in alcohol, triacetin.
• CAS DataBase Reference: 2-FURYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FURYLACETONE(6975-60-6)
• EPA Substance Registry System: 2-FURYLACETONE(6975-60-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39
• TSCA: Yes
• Hazardous Substances Data: 6975-60-6(Hazardous Substances Data)

Usage

Description

(2-Furyl)-2-propanone has an odor and taste suggestive of radish. This substance is synthesized by heating the α-methyl-p-(α-furyl) glycidic acid ethyl in aqueous NaOH.

Chemical Properties

(2-Furyl)-2-propanone has an odor and taste suggestive of radish.

Occurrence

Reported found in roasted coffee, roasted onion, cooked potato, wheaten bread, fried beef, pork liver, sherry, soybeans and sukiyaki

Uses

Suitable for fragrance applications.2-Furylacetone is used as the reactant in the synthesis and transformations of furan derivatives

Preparation

By heating the α-methyl-β-(α-furyl) glydidic acid ethyl in aqueous NaOH.

InChI:InChI=1/C7H8O2/c1-6(8)5-7-3-2-4-9-7/h2-4H,5H2,1H3

Upstream product

• 109962-79-0 2,3-epoxy-3-[2]furyl-2-methyl-propionic acid methyl ester 
• 88795-82-8 ethyl ester of the 2-methyl-3-(2-furyl)-2,3-epoxypropionic acid 
• 75135-41-0 3-(2-Furyl)prop-1-ene 
• 98-01-1 furfural 
• 181211-54-1 2-nitro-1-(2-furyl)propane 
• 84784-37-2 1-Furan-2-yl-1-methylsulfanyl-propan-2-one 
• 66040-54-8 1-(furan-2-yl)-propan-2-ol 
• 110-00-9 furan 
• 67-64-1 acetone 
• 134538-48-0 (E)-2-(2-nitroprop-1-en-1-yl)furan 

Downstream Products

• 66040-54-8 1-(furan-2-yl)-propan-2-ol 

Relevant articles and documents

Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols

The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).

Gold catalysis: benzanellation versus alkylidenecyclopentenone synthesis

A series of different furan-yn-ols were prepared by a three-step sequence. Their reaction with Gagosz's catalyst Ph3PAuNTf2 depends strongly on the substitution pattern of the substrate and the quality of the leaving group. Benzofurans, alkylidenecyclopentenones or Meyer-Schuster type products can be obtained. Improving the leaving group quality leads to the preferred formation of benzofurans.

Novel Compounds

The invention relates to heteroaromatic carboxamides of formula (I), wherein A, R1, R2 and X are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.