| Identification | More | [Name]
Difurfuryldisulfide | [CAS]
4437-20-1 | [Synonyms]
2,2-DITHIOBIS(METHYLENE)BISFURAN
2,2-(DITHIODIMETHYLENE) DIFURAN
2,2'-(DITHIODIMETHYLENE)DIFURAN
BIS-(2-FURFURYL)DISULFIDE
DIFURFURYL DISUFIDE
DIFURFURYL DISULFIDE
DIFURFURYL DISULPHIDE
FEMA 3146
FURFURYL DISULFIDE
LABOTEST-BB LT00159862
2-([(2-Furylmethyl)disulfanyl]methyl)furan
2,2’-[dithiobis(methylene)]bis-fura
bis(2-furylmethyl) disulphide
bis(2-furylmethyl)disulfide
bis-(Furylmethyl) disulfide
bis-Furfuryl disulfide
di-2-furfuryl disulfide
Furan, 2,2'-[dithiobis(methylene)]bis-
2 2'-(DITHIODIMETHYLENE)DIFURAN 95+%
2-FURFURYLDISULPHIDE | [EINECS(EC#)]
224-649-6 | [Molecular Formula]
C10H10O2S2 | [MDL Number]
MFCD00010082 | [Molecular Weight]
226.32 | [MOL File]
4437-20-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [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 | [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 Gravity]
1.235 (20/4℃) | [Odor]
at 0.01 % in propylene glycol. sulfury coffee roasted chicken meaty onion cabbage | [biological source]
synthetic | [Odor Type]
coffee | [JECFA Number]
1081 | [Major Application]
flavors and fragrances | [InChI]
1S/C10H10O2S2/c1-3-9(11-5-1)7-13-14-8-10-4-2-6-12-10/h1-6H,7-8H2 | [InChIKey]
CBJPZHSWLMJQRI-UHFFFAOYSA-N | [SMILES]
C(SSCc1ccco1)c2ccco2 | [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]
4437-20-1(EPA Substance) |
| Safety Data | Back Directory | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3334 | [WGK Germany ]
3
| [TSCA ]
TSCA listed | [HS Code ]
29321900 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [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. | [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 |
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