4437-20-1

Basic information

• Product Name: Difurfuryldisulfide
• Synonyms: Difurfuryl disulfide, Furfuryl disulfide;2-(Furan-2-ylmethyldisulfanylmethyl)furan;Bis(2-furanylmethyl) persulfide;Bis(furfuryl) persulfide;Di(furfuryl) persulfide;Difurfuryl persulfide;Difurfuryldisulfide,96%;Difurfuryl disulfide >=95.0%
• CAS NO: 4437-20-1
• Molecular Formula: C₁₀H₁₀O₂S₂
• Molecular Weight: 226.32
• EINECS: 224-649-6
• Product Categories: Sulfides flavors;Building Blocks;C8 to C11;Chemical Synthesis;Furans;Heterocyclic Building Blocks;Furan&Benzofuran;API intermediates;sulfide Flavor
• Mol File: 4437-20-1.mol
• Article Data: 46

Chemical Properties

• Melting Point: 10-11 °C(lit.)
• Boiling Point: 112-115 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.233 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000462mmHg at 25°C
• Refractive Index: n20/D 1.585(lit.)
• Storage Temp.: 0-10°C
• CAS DataBase Reference: Difurfuryldisulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Difurfuryldisulfide(4437-20-1)
• EPA Substance Registry System: Difurfuryldisulfide(4437-20-1)

Safety Data

• Safety Statements: 24/25
• RIDADR: UN 3334
• WGK Germany: 3
• Hazardous Substances Data: 4437-20-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Occurrence

Reported found in beef (boiled, cooked) and coffee

Uses

Furfuryl disulfide has been used in the preparation of poly(disulfido-imide)s by Diels-Alder (DA) reaction with the various bismaleimides.

Taste threshold values

Taste characteristics at 20 ppm: roasted, sulfuraceous, alliaceous, green and meaty.

General Description

Difurfuryl disulfide is a sulfur-containing volatile compound mainly found in roasted coffee. It is also the main degradation product of furfuryl mercaptan under Fenton-type reaction conditions.

InChI:InChI=1/C10H10O2S2/c1-3-9(11-5-1)7-13-14-8-10-4-2-6-12-10/h1-6H,7-8H2

Upstream product

• 98-02-2 2-thiolomethyl-furan 
• 696-63-9 4-Methoxybenzenethiol 
• 89712-86-7 potassium O-furfuryl dithiocarbonate 
• 10147-36-1 n-propanesulfonyl chloride 
• 50906-77-9 3,3′-dithiobis(propanoic dihydrazide) 
• 123-08-0 4-hydroxy-benzaldehyde 
• 72678-98-9 2-(2-furyl)-1,3-thiazolide-4-carboxylic acid 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 536-74-3 phenylacetylene 
• 431-03-8 dimethylglyoxal 
• 600-14-6 2,3-Pentanedione 
• 98-01-1 furfural 

Downstream Products

• 98-02-2 2-thiolomethyl-furan 
• 57500-00-2 methyl furfuryl disulfide 
• 3260-09-1 2-((phenylthio)methyl)furan 
• 13678-68-7 S-(furan-2-ylmethyl) ethanethioate 
• 126265-85-8 N-cyclohexylfuran-2-carbothioamide 
• 61296-23-9 furan-2-yl(morpholino)methanethione 

Relevant articles and documents

Green Aerobic Oxidation of Thiols to Disulfides by Flavin-Iodine Coupled Organocatalysis

Coupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.

Transition Metal-Free Oxidative Coupling of Primary Amines in Polyethylene Glycol at Room Temperature: Synthesis of Imines, Azobenzenes, Benzothiazoles, and Disulfides

A transition metal-free protocol has been developed for the oxidative coupling of primary amines to imines and azobenzenes, thiols to disulfides, and 2-aminothiophenols to benzothiazoles, offering excellent yields. The advantageous features of the present environmentally benign methodology include the usage of biocompatible and green reaction conditions such as, solvent, room temperature reactions and transition metal-free approach. Moreover, it offers a broader substrate scope.

Laccase-catalyzed in situ generation and regeneration of N-phenyltriazolinedione for the aerobic oxidative homo-coupling of thiols to disulfides

The first report on aerobic in situ generation and regeneration of N-phenyltriazolinedione, a valuable oxidizing agent, from a catalytic amount of N-phenyl urazole in the presence of a laccase enzyme is presented. The application of a 4-phenyl urazole/Laccase/O2 as a new cooperative catalytic oxidation system is reported for a transition-metal-free and halogen free oxidative homo-coupling reaction of structurally diverse thiols to their corresponding disulfides with good to excellent yields in a phosphate buffer solution under mild reaction conditions.