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

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

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

Downstream Products

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

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.

Preparation and characterization of Cu (II) Schiff base complex functionalized boehmite nanoparticles and its application as an effective catalyst for oxidation of sulfides and thiols

The synthesis, characterization, and evaluation of a Schiff base Cu (II) complex functionalized boehmite nanoparticles (Cu-complex-boehmite) as a new catalyst for oxidation of sulfides and thiols in the presence of hydrogen peroxide with complete selectivity and high conversion under solvent-free and mild reaction conditions were reported. Characterization of the catalyst was performed with various physicochemical methods. This effective catalyst was evaluated in terms of activity and reusability. It indicated high catalytic activity, good recoverability and reusability, and supplied the corresponding products in high yields and short reaction times. In addition, it shows notable advantages such as simplicity of operation, heterogeneous nature, easy work up, and it could be used at least eight times with no significant loss of its activity.

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.

Unsymmetrical Disulfides Synthesis via Sulfenium Ion

An umpolung approach for the synthesis of unsymmetrical disulfides via sulfenium ion is reported. In situ generated electrophilic sulfenium ion from electron-rich thiols reacted with second thiols to yield unsymmetrical disulfides. Using an iodine catalyst and 4-dimethylaminopyridine (DMAP)/water as promoter, the target syntheses were achieved in one pot under aerobic condition.

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.

Thermal conversion of primary alcohols to disulfides: Via xanthate intermediates: An extension to the Chugaev elimination

Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination which yields olefins. The current research provides easy access to dialkyl disulfides from commercially available primary alkanols.

Oxidative dimerization of thiols to disulfide using recyclable magnetic nanoparticles

Abstract: Dimerization of thiol groups to disulfide is an important transformation in chemical processes. In this study, magnetic ion exchanged Montmorillonite-k10 was synthesized and characterized using FTIR, X-ray diffraction and scanning electron microscope techniques. Then, the application of the synthesized catalyst as an efficient oxidizing agent was evaluated in oxidative dimerization of different thiols to corresponding disulfides under optimal reaction conditions. The reaction was easily performed with aromatic, aliphatic and heterocyclic thiols. The magnetic catalyst was easily recovered by applying an external magnet and, further, was reused in successive reactions. Graphical Abstract: [Figure not available: see fulltext.]

An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor

A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented. Water is used as the source of oxygen to enable the oxidation process. The oxidation reaction utilizes the same reagents in all scenarios and the selectivity is solely governed by the applied potential. The procedure exhibits a broad scope and good functional group compatibility providing access to various sulfoxides (15 examples), sulfones (15 examples) and disulfides (6 examples). The use of continuous flow allows the optimal reaction parameters (e.g. residence time, applied voltage) to be rapidly assessed, to avoid mass- and heat-transfer limitations and to scale the electrochemistry.

Metal-Free Photocatalytic Aerobic Oxidation of Thiols to Disulfides in Batch and Continuous-Flow

Disulfides represent significant molecular and structural features in various biologically active compounds and fine chemicals. Therefore, the development of mild, efficient and sustainable methods to access disulfides is of great importance. Here, we describe the development of a mild metal-free photocatalytic aerobic oxidation of thiols to disulfides using Eosin Y and visible-light irradiation. A continuous flow procedure was developed to accelerate the photocatalytic process, enabling the preparation of disulfides with high purity in a timeframe of minutes. The mildness and applicability of our method was exemplified by the flow synthesis of the cyclic peptide hormone, oxytocin, requiring only a 200s reaction time and an efficient one-pot batch protocol for the preparation of the therapeutic thiuram disulfide, disulfiram.

Ultrasound-Accelerated Synthesis of Asymmetrical Thiosulfonate S-Esters by Base-Promoted Reaction of Sulfonyl Chlorides with Thiols

Amberlyst A-26, Mg-Al hydrotalcite, potassium fluoride absorbed on alumina, triethylamine and pyridine have been tested as base catalysts and reagents for the reaction of sulfonyl chlorides with thiols to prepare thiosulfonate S-esters. The reactions were performed under solvent-free conditions or with a minimum amount of solvent assisted by magnetic stirring, ultrasound irradiation and microwave irradiation. Ultrasound irradiation has good effects on the synthesis of sterically hindered thiosulfonate S-esters in solvent-free media as well as in a minimum amount of anhydrous diethyl ether.