1438-91-1

Basic information

• Product Name: Furfuryl methyl sulfide
• Synonyms: 2-(Methylthio)methylfuran;2-[(methylthio)methyl]-fura;2-[(methylthio)methyl]-Furan;2-furfuryl methyl sulfide;2-Furfuryl methyl sulphide;Furan, 2-[(methylthio)methyl]-;methylfurfurysulfide;METHYL FURFURYL SULFIDE
• CAS NO: 1438-91-1
• Molecular Formula: C₆H₈OS
• Molecular Weight: 128.19
• EINECS: 215-874-0
• Product Categories: sulfide Flavor;Alphabetical Listings;E-F;Flavors and Fragrances
• Mol File: 1438-91-1.mol

Chemical Properties

• Boiling Point: 64-65 °C15 mm Hg(lit.)
• Flash Point: 146 °F
• Appearance: Clear yellow to green or light brown/Liquid
• Density: 1.07 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.58mmHg at 25°C
• Refractive Index: n20/D 1.521(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 107109
• CAS DataBase Reference: Furfuryl methyl sulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Furfuryl methyl sulfide(1438-91-1)
• EPA Substance Registry System: Furfuryl methyl sulfide(1438-91-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-37
• RIDADR: UN 3334
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1438-91-1(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Furfuryl methyl sulfide is used as a flavoring agent for its strong and pungent odor, which can add depth and complexity to various food products. Its unique combination of onion-garlic-radish-mustard notes, along with a coffee-like aroma, makes it a valuable addition to the flavor industry.
Used in Fragrance Industry:
Due to its strong sulfur and coffee-like odor, furfuryl methyl sulfide can be used as a component in the fragrance industry to create unique and distinct scents for perfumes, colognes, and other scented products.
Used in Chemical Research:
Furfuryl methyl sulfide's distinct chemical properties make it a valuable compound for research purposes in the chemical industry. It can be used in the development of new materials, the study of chemical reactions, and the exploration of various applications in different fields.
Used in Analytical Chemistry:
The unique odor and taste characteristics of furfuryl methyl sulfide make it useful in analytical chemistry for the detection and identification of certain compounds, as well as in the development of sensors and analytical methods for monitoring specific substances in various environments.

Preparation

From 2-furfuryl mercaptan and dimethyl sulfate.

InChI:InChI=1/C6H8OS/c1-8-5-6-3-2-4-7-6/h2-4H,5H2,1H3

Upstream product

• 124-41-4 sodium methylate 
• 98-02-2 2-thiolomethyl-furan 
• 77-78-1 dimethyl sulfate 
• 98-00-0 (2-furyl)methyl alcohol 
• 74-88-4 methyl iodide 
• 18185-54-1 (+/-)-2-furfuryl methyl sulfoxide 
• 170024-06-3 O-furfuryl-S-methyl dithiocarbonate 
• 75-15-0 carbon disulfide 

Relevant articles and documents

A Facile One-pot Synthesis of Sulfides from Alkyl Halides and Alcohols Using Tetramethylthiourea

Sulfides can be readily prepared under mild conditions by a reaction of tetramethylthiourea with alkyl halides and alcohols in the presence of sodium hydride in satisfactory yields.The scope and limitation of this method are also presented.

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

Structure-Odor Correlations in Homologous Series of Mercapto Furans and Mercapto Thiophenes Synthesized by Changing the Structural Motifs of the Key Coffee Odorant Furan-2-ylmethanethiol

Furan-2-ylmethanethiol (2-furfurylthiol; 2-FFT, 1) is long-known as a key odorant in roast and ground coffee and was also previously identified in a wide range of thermally treated foods such as meat, bread, and roasted sesame seeds. Its unique coffee-like odor quality elicited at very low concentrations, and the fact that only a very few compounds showing a similar structure have previously been described in foods make 1 a suitable candidate for structure-odor activity studies. To gain insight into the structural features needed to evoke a coffee-like odor at low concentrations, 46 heterocyclic mercaptans and thio ethers were synthesized, 32 of them for the first time, and their odor qualities and odor thresholds were determined. A movement of the mercapto group to the 3-position kept the coffee-like aroma but led to an increase in odor threshold. A separation of the thiol group from the furan ring by an elongation of the carbon side chain caused a loss of the coffee-like odor and also led to an increase in odor thresholds, especially for ω-(furan-2-yl)alkane-1-thiols with six or seven carbon atoms in the side chain. A displacement of the furan ring by a thiophene ring had no significant influence on the odor properties of most of the compounds studied, but the newly synthesized longer-chain 1-(furan-2-yl)- and 1-(thiophene-2-yl)alkane-1-thiols elicited interesting passion fruit-like scents. In total, only 4 out of the 46 compounds also showed a coffee-like odor quality like 1, but none showed a lower odor threshold. Besides the odor attributes, also retention indices, mass spectra, and NMR data of the synthesized compounds were elaborated, which are helpful in possible future identification of these compounds in trace levels in foods or other materials.

Potassium fluoride on alumina: A convenient synthesis of O-alkyl methyldithiocarbonates. Pyrolysis of O-benzyl-S-methyldithiocarbonates

Xanthates were easily prepared by adsorption of alcohol on KF-Al2O3 followed by treatment of carbon disulfide and iodomethane at room temperature. Pyrolysis of benzyl xanthate affords to a complex mixture of products. A radical process was proposed to explain the nature of products obtained.

Simple synthesis of furfuryl sulfides via extrusion of COS from the xanthates and its mechanistic aspects

Heating of O-furfuryl S-alkyl dithiocarbonates (xanthates) gave furfuryl alkyl sulfides together with S-furfuryl S-alkyl dithiocarbonates.The crossover reaction using differently substituted furfuryl xanthates in polar solvents indicates that the reaction proceeds intermolecularly, whereas the reaction in non-polar solvents showed intramolecular reaction behaviour.The reaction is first-order and the rates are considerably affected by a change in the solvent polarity.The activation enthalpy and entropy for the extrusion of O-furfuryl S-methyl xanthate in xylene are 28.0 +/- 1.3 kcal mol-1 and -2 +/- 4 cal K-1 mol-1, respectively.Based on these findings together with the MO calculation data, the mechanism for the conversion reaction of furfuryl xanthates to furfuryl alkyl sulfides is discussed.

Pharmaceutically useful furyl substituted dihydroxyethylbutyrolactones

The compounds 2-(5-methylthiomethyl-2-furyl)-2-hydroxy-3-keto-4- dihydroxyethylbutyrolactone and 2-(5-methoxymethyl-2- furyl)-2-furyl(-2-hydroxy-3-keto-4-dihydroxyethylbutyrolactone and pharmaceutical compositions containing them are useful to regulate the immune response in mammals.

Method of treating inflammation in mammals utilizing ketobutyrolactones and furylbutyrolactones

Treatment of inflammation in mammals utilizing selected ketobutyrolactones and furylbutyrolactones. Treatment is applicable to both acute or chronic inflammation. Antiviral activity of methylfurylbutyrolactone is also disclosed.