13678-67-6

Basic information

• Product Name: Difurfurylsulfide
• Synonyms: 2-([(2-Furylmethyl)sulfanyl]methyl)furan;2,2’-[thiobis(methylene)]bis-fura;2,2’-[Thiobis(methylene)]bisfuran;2,2’-[thiobis(methylene)]bis-Furan;bis(2-furylmethyl) sulfide;di-2-furfuryl sulfide;Furan, 2,2'-[thiobis(methylene)]bis-;Furan,2,2’-[thiobis(methylene)]bis-
• CAS NO: 13678-67-6
• Molecular Formula: C₁₀H₁₀O₂S
• Molecular Weight: 194.25
• EINECS: 237-172-3
• Product Categories: sulfide Flavor;Building Blocks;C8 to C11;Chemical Synthesis;Furans;Heterocyclic Building Blocks
• Mol File: 13678-67-6.mol

Chemical Properties

• Melting Point: 29-34 °C(lit.)
• Boiling Point: 135-143 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to brown/Low Melting Solid or Liquid
• Density: 139
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: n20/D 1.556(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• BRN: 1371700
• CAS DataBase Reference: Difurfurylsulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Difurfurylsulfide(13678-67-6)
• EPA Substance Registry System: Difurfurylsulfide(13678-67-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 13678-67-6(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Difurfurylsulfide is used as an additive in the flavor industry to enhance the aroma and taste of various products. Its strong coffee-like scent makes it a popular choice for creating natural and artificial flavors for the food and beverage sector.
Difurfurylsulfide is used as a flavor enhancer for coffee, cocoa, sesame oil, and meat products, providing a rich and authentic roasted coffee aroma that improves the overall sensory experience of these items.

Preparation

By refluxing a mixture of 2-furyl-methanethiol in ethanolic KOH and furfuryl bromide in ether.

InChI:InChI=1/C10H10O2S/c1-3-9(11-5-1)7-13-8-10-4-2-6-12-10/h1-6H,7-8H2

Upstream product

• 98-02-2 2-thiolomethyl-furan 
• 431-03-8 dimethylglyoxal 
• 28588-74-1 2-methylfuran-3-thiol 
• 1395105-45-9 difurfuryl sulfoxide 

Downstream Products

• 1383805-16-0 diphenyl[(furfurylsulfidyl)sulfonium triflate] 

Relevant articles and documents

SULFUR EXTRUSION FROM DISULFIDES BY CARBENES

The present invention relates to a method for preparing a compound T having a thioether group from a compound D having a disulfide group in the presence of a carbene.

Oxo-rhenium(V) complexes containing heterocyclic ligands as catalysts for the reduction of sulfoxides

This work reports the catalytic activity of a large variety of oxo-rhenium(V) complexes (1 mol-%) containing the ligands 2-(2-hydroxy-5- methylphenyl)benzotriazole (Hhmpbta), 2-(2-hydroxyphenyl)benzothiazole (Hhpbt), 2-(2-hydroxyphenyl)benzoxazole (Hhpbo), and 2-(2-hydroxyphenyl)-1H-benzimidazole (Hhpbi) in the deoxygenation of sulfoxides with silanes or boranes as the reducing agents. In general, all of the complexes are excellent catalysts, although the PhSiH3/[ReOBr2(hmpbta)(PPh3)] and pinacolborane/[ReOBr2(hmpbta)(PPh3)] systems are the most efficient for the reduction of aromatic and aliphatic sulfoxides and tolerate different functional groups. Copyright

Oxo-Rhenium(V) Complexes Containing Heterocyclic Ligands as Catalysts for the Reduction of Sulfoxides

This work reports the catalytic activity of a large variety of oxo-rhenium(V) complexes (1 mol-%) containing the ligands 2-(2-hydroxy-5-methylphenyl)benzotriazole (Hhmpbta), 2-(2-hydroxyphenyl)benzothiazole (Hhpbt), 2-(2-hydroxyphenyl)benzoxazole (Hhpbo), and 2-(2-hydroxyphenyl)-1H-benzimidazole (Hhpbi) in the deoxygenation of sulfoxides with silanes or boranes as the reducing agents. In general, all of the complexes are excellent catalysts, although the PhSiH3/[ReOBr2(hmpbta)(PPh3)] and pinacolborane/[ReOBr2(hmpbta)(PPh3)] systems are the most efficient for the reduction of aromatic and aliphatic sulfoxides and tolerate different functional groups.

Highly efficient rhenium-catalyzed deoxygenation of sulfoxides without adding any reducing agent

This work reports a novel method for the deoxygenation of aromatic and aliphatic sulfoxides catalyzed by oxo-rhenium complexes without adding any reducing agent. The oxo-rhenium complex ReOCl3(PPh3) 2 proved to be very efficient for the deoxygenation of several sulfoxides with tolerance of different functional groups.

Some Novel Meatlike Aroma Compounds from the Reactions of Alkanediones with Hydrogen Sulfide and Furanthiols

The products of reactions of hydrogen sulfide with 2,3-butanedione and with 2,3-pentanedione in dilute ethanolic solution were analyzed by GC-MS and GC-odor port analysis.Components were also collected from the GC column and analyzed by 1H NMR.Mercaptoketones were formed which readily oxidized to the corresponding disulfides with traces of mono- and trisulfides.When 2-methyl-3-furanthiol or 2-furylmethanethiol was added to the reaction mixtures, a series of disulfides containing alkanone, 2-methyl-3-furyl and 2-furanmethyl moieties were formed.Some of these compounds have been found recently in the volatiles of cooked meat and in meatlike model systems.GC-odor port evaluation of the components of the reaction systems showed that disulfides containing the 2-methyl-3-furyl group had meaty aromas, whereas those without this group were sulfurous or onion-like in character.Keywords: Aroma; meat; mercaptoketones; disulfides