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.)

refractive index 

n20/D 1.585(lit.)

FEMA 

3146 | 2,2'-(DITHIODIMETHYLENE)-DIFURAN

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

clear liquid

color 

Colorless to Yellow

Specific Gravity

1.235 (20/4℃)

Odor

at 0.01 % in propylene glycol. sulfury coffee roasted chicken meaty onion cabbage

Odor Type

coffee

biological source

synthetic

JECFA Number

1081

LogP

4.03

CAS DataBase Reference

4437-20-1(CAS DataBase Reference)

NIST Chemistry Reference

Bis(2-furfuryl)disulfide(4437-20-1)

EPA Substance Registry System

Furan, 2,2'-[dithiobis(methylene)]bis- (4437-20-1)

Safety Information

Safety Statements 

24/25

RIDADR 

UN 3334

WGK Germany 

3

HS Code 

29321900

MSDS

• Language:English Provider:2,2'-(Dithiodimethylene)-difuran
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Difurfuryldisulfide Usage And Synthesis

Chemical Properties

Pale yellowish oily liquid. Slightly soluble in water, soluble in alcohol and oils.

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.

Definition

ChEBI: Bis(2-furanylmethyl) disulfide is a heteroarene.

Preparation

Difurfuryl disulfide is produced from Furfural and Hydrogen sulfide gas.

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.

Synthesis

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

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