13678-59-6

Basic information

• Product Name: 5-METHYL-2-(METHYLTHIO)FURAN
• Synonyms: 5-METHYL-2-(METHYLTHIO)FURAN;2-METHYL-5-(METHYLMERCAPTO)FURAN;2-METHYL-5-(METHYLTHIO)FURAN;FEMA 3366;METHYL 5-METHYLFURYL SULFIDE;2-Methyl-5-(methylsulfanyl)furan;2-methyl-5-(methylthio)-fura;5-Methyl-2-methylthiofurane
• CAS NO: 13678-59-6
• Molecular Formula: C₆H₈OS
• Molecular Weight: 128.19
• EINECS: 237-170-2
• Product Categories: sulfide Flavor
• Mol File: 13678-59-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 79-81°C 50mm
• Flash Point: 79-81°C/50mm
• Appearance: COA
• Density: 1.063
• Vapor Pressure: 2.85mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 5-METHYL-2-(METHYLTHIO)FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-2-(METHYLTHIO)FURAN(13678-59-6)
• EPA Substance Registry System: 5-METHYL-2-(METHYLTHIO)FURAN(13678-59-6)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22
• Safety Statements: 16
• RIDADR: 3271
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 13678-59-6(Hazardous Substances Data)

Usage

Description

5-METHYL-2-(METHYLTHIO)FURAN, also known as 2-Methyl-5-(methylthio)furan, is an organic compound with a very strong sulfurated odor. It is characterized by its musty, mustard, onion, garlic, mushroom, coffee, and savory nuances when present at a concentration of 50 ppm. 5-METHYL-2-(METHYLTHIO)FURAN can be synthesized from 2-methylfuran using CH3SCl or an organolithium compound.

Uses

Used in Flavor and Fragrance Industry:
5-METHYL-2-(METHYLTHIO)FURAN is used as a flavoring agent for its musty, mustard, onion, garlic, mushroom, coffee, and savory nuances. Its strong sulfurated odor makes it suitable for enhancing the taste and aroma of various food products.
Used in Coffee Industry:
5-METHYL-2-(METHYLTHIO)FURAN is used as a flavoring agent in the coffee industry, where it contributes to the characteristic taste and aroma of coffee. Its presence as a constituent of coffee adds depth and complexity to the overall flavor profile.
Used in Chemical Synthesis:
5-METHYL-2-(METHYLTHIO)FURAN can be used as a starting material or intermediate in the synthesis of various organic compounds, particularly those with sulfur-containing functional groups. Its strong sulfurated odor and unique chemical properties make it a valuable building block for the development of new molecules with potential applications in various industries.

Preparation

From 2-methylfuran with CH3SCl; from 2-methylfuran with an organolithium compound.

InChI:InChI=1/C6H8OS/c1-5-3-4-6(7-5)8-2/h3-4H,1-2H3

Upstream product

• 534-22-5 2-methylfuran 
• 624-92-0 Dimethyldisulphide 
• 13129-38-9 2-(methylsulfanyl)-furan 
• 116394-76-4 methyl 2-(5-methylfuryl) sulfoxide 

Downstream Products

• 26246-30-0 2-methyl-5-(methylthio)benzoic acid 
• 113789-82-5 (E)-4-Oxo-pent-2-enethioic acid S-methyl ester 
• 113789-81-4 (Z)-4-Oxo-pent-2-enethioic acid S-methyl ester 

Relevant articles and documents

Preparation and Reaction of Methylthiofurans

By lithiation of 3,4-dimethoxyfuran, 2-methylfuran and furan, followed by reaction with dimethyldisulfide, the methylthiofurans 2, 8, and 10 have been prepared.Reaction of 8 with maleic anhydride has yielded 6-methy1-3-(methylthio)phthalic anhydride (9), a yellow substance with a strong greenish fluorescence, obviously formed by elimination of H2O from an unstable cycloadduct.An analogous reaction of 2 resulted in an unexpected mixture from which the following yellow compounds were isolated: 3-hydroxy-4,5-dimethoxy-6-(methylthio)phthalic anhydride (3), 4hydroxy-5-methoxy-3,6-bis(methylthio)phthalic anhydride (4), and bis(S-methyl) (2Z,4E,6Z)-2,3,6,7 -tetramethoxy-4,5-bis(methylthio)-2,4,6-octatrienethioate (5).Compound 5 is also formed on standing of 2 at RT.Mild acid hydrolysis of 2 results in ring-opening accompanied by an intramolecular oxido-reduction to yield S-methyl(3Z)-3-methoxy-4-(methylthio)-2-oxo-3-butenethioate (6a).The structures of compounds 5 and 6a have been determined by X-ray analysis.

An analysis of substituent effects on 1H and 13C NMR parameters of substituted furans. Linear free energy relationships and PM3 semiempirical calculations

Forty five furans have been obtained in a synthetic project designed to evaluate monothiosubstituted furans as potential food flavourings. A full NMR (1H and 13C) study and PM3 molecular orbital semiempirical calculations have been carried out. Substituent-induced chemical shifts (SCS) for six and nine substituents at the 2- and 3-positions have been calculated and a separation of inductive and resonance effects of these substituents has been proposed. Finally, a linear correlation between the net atomic charges localized at ring carbons and their 13C NMR chemical shifts has been established.

A Tandem Oxidation-Intramolecular Diels-Alder Reaction

Oxidation of the furan (4) with pyridinium chlorochromate gave the intramolecular Diels-Alder cycloadduct (6) as the major product, presumably via the intermediate.