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Difurfuryldisulfide

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  • CAS:4437-20-1
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Difurfuryldisulfide Basic information
Product Name:Difurfuryldisulfide
Synonyms:BIS-(2-FURFURYL)DISULFIDE;FURFURYL DISULFIDE;FEMA 3146;DIFURFURYL DISUFIDE;DIFURFURYL DISULFIDE;DIFURFURYL DISULPHIDE;LABOTEST-BB LT00159862;2-FURFURYLDISULPHIDE
CAS:4437-20-1
MF:C10H10O2S2
MW:226.32
EINECS:224-649-6
Product Categories:Building Blocks;C8 to C11;Chemical Synthesis;Furans;Heterocyclic Building Blocks;Sulfides flavors;Furan&Benzofuran;API intermediates;sulfide Flavor
Mol File:4437-20-1.mol
Difurfuryldisulfide Structure
Difurfuryldisulfide Chemical Properties
Melting point 10-11 °C (lit.)
Boiling point 112-115 °C/0.5 mmHg (lit.)
density 1.233 g/mL at 25 °C (lit.)
FEMA 3146 | 2,2'-(DITHIODIMETHYLENE)-DIFURAN
refractive index n20/D 1.585(lit.)
Fp >230 °F
storage temp. Keep in dark place,Inert atmosphere,2-8°C
form clear liquid
color Colorless to Yellow
Specific Gravity1.235 (20/4℃)
Odorat 0.01 % in propylene glycol. sulfury coffee roasted chicken meaty onion cabbage
Odor Typecoffee
biological sourcesynthetic
JECFA Number1081
Major Applicationflavors and fragrances
InChI1S/C10H10O2S2/c1-3-9(11-5-1)7-13-14-8-10-4-2-6-12-10/h1-6H,7-8H2
InChIKeyCBJPZHSWLMJQRI-UHFFFAOYSA-N
SMILESC(SSCc1ccco1)c2ccco2
LogP4.03
CAS DataBase Reference4437-20-1(CAS DataBase Reference)
NIST Chemistry ReferenceBis(2-furfuryl)disulfide(4437-20-1)
EPA Substance Registry SystemFuran, 2,2'-[dithiobis(methylene)]bis- (4437-20-1)
Safety Information
Safety Statements 24/25
RIDADR UN 3334
WGK Germany 3
TSCA TSCA listed
HS Code 29321900
Storage Class10 - Combustible liquids
MSDS Information
ProviderLanguage
2,2'-(Dithiodimethylene)-difuran English
ACROS English
SigmaAldrich English
Difurfuryldisulfide Usage And Synthesis
Chemical PropertiesPale yellowish oily liquid. Slightly soluble in water, soluble in alcohol and oils.
OccurrenceReported found in beef (boiled, cooked) and coffee
UsesFurfuryl disulfide has been used in the preparation of poly(disulfido-imide)s by Diels-Alder (DA) reaction with the various bismaleimides.
DefinitionChEBI: Bis(2-furanylmethyl) disulfide is a heteroarene.
PreparationDifurfuryl disulfide is produced from Furfural and Hydrogen sulfide gas.
Taste threshold valuesTaste characteristics at 20 ppm: roasted, sulfuraceous, alliaceous, green and meaty.
General DescriptionDifurfuryl 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.
Synthesis
Furfuryl mercaptan

98-02-2

Difurfuryldisulfide

4437-20-1

The general procedure for the synthesis of difurfuryldisulfide from furfuryl(base)thiols was as follows: a non-homogeneous mixture of 4-chlorobenzenethiol (0.145 g, 1 mmol) with KBrO3 (0.167 g, 1 mmol), (NH4)6Mo7O24-4H2O (0.124 g, 10 mmol), and CH3CN/H2O (7:3, 5 mL) was mixed. The reaction mixture was stirred in a fume hood for 4 min under ambient atmosphere and at room temperature. The reaction progress was monitored by thin layer chromatography (TLC) using EtOAc/n-C6H14 (1:13) as eluent. Upon completion of the reaction, CH2Cl2 (20 mL) was added and the reaction mixture was filtered. The filtrate was washed sequentially with 5% NaOH solution and water and then dried with anhydrous MgSO4. Finally, the difurfuryldisulfide product of sufficient purity was obtained by evaporating the solvent.

References[1] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 3, p. 685 - 691
[2] Synthesis, 2007, # 21, p. 3286 - 3289
[3] Journal of Chemical Research - Part S, 2002, # 11, p. 564 - 566
[4] Synthetic Communications, 2011, vol. 41, # 2, p. 170 - 176
[5] Journal of Organic Chemistry, 1995, vol. 60, # 11, p. 3266 - 3267
Tag:Difurfuryldisulfide(4437-20-1) Related Product Information
Piperonyl butoxide DL-Dithiothreitol Diallyldisulfide Dimethyl disulfide Methylene dithiocyanate Selenium sulfide Difurfuryl sulfide Acetoin Dibromomethane 3-(Methylthio)propionaldehyde Furfuryl propionate ester Methyl furfuryl disulfide Furan-2-yl-methanethiol 2-Methylfuran Diethyl disulfide GGKPDLRPCHPPCHYIPRPKPR Difurfuryldisulfide