2,2'-(Dithiodimethylene)difuran
Basic information
- CAS
4437-20-1- Standard SMILES
c1coc(CSSCc2ccco2)c1- InChIKey
CBJPZHSWLMJQRI-UHFFFAOYSA-N- Molecular formula
- C10H10O2S2
- Average molar mass
- 226.3 g/mol
- Monoisotopic mass
- 226.0122219
Overview
Bis(2-furanylmethyl) disulfide is a heteroarene.
Names & identifiers
- Preferred name
- 2,2'-(Dithiodimethylene)difuran
- IUPAC
- 2-[(furan-2-ylmethyldisulfanyl)methyl]furan
- English name
- Difurfuryldisulfide
- Molecular formula
- C10H10O2S2
- Molecular weight
- 226.32
Names & synonyms
DIFURFURYL DISULFIDEFurfuryl disulfideFuran, 2,2'-[dithiobis(methylene)]bis-2,2'-(Dithiodimethylene)difuran2-Furfuryl disulfidecoffee difuranBis(2-furfuryl)disulfideBis(2-furfuryl) disulfideFEMA No. 31462,2'-(thiodimethylene)-difuran2,2'-(Dithiobis(methylene))bisfuran2,2'-[Dithiobis(methylene)]bisfuran
Show more names
DIFURFURYL DISULPHIDE1,2-Bis(furan-2-ylmethyl)disulfaneFEMA 3146DifurfuryL2-(Furan-2-ylmethyldisulfanylmethyl)furanDifuryl disulfideDifurfuryldisulfid
5IP6729ULFDIFURFURYL DISUFIDEEINECS 224-649-6Furan, 2,2'-(dithiodimethylene)di-Furan, 2,2'-(dithiobis(methylene))bis-DTXSID30634632,2'-(THIODIMETHYLENE)-DIFURAN [FHFI]RefChem:440152
Database identifiers
- CAS
4437-20-1- PubChem CID
- 20499
- DTXSID
DTXSID3063463- ChEMBL
CHEMBL1331840- ChEBI
CHEBI:171681- UNII
- 5IP6729ULF
- EC Number
- 224-649-6
- Nikkaji
- J68.898C
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 76.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 148
Experimental & physicochemical properties
FragrancesFragrance Ingredient (2,2'-(Dithiodimethylene)-difuran) -> IFRA transparency List
LogP4.030
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.229-1.248
Flavoring AgentsEU Flavoring substances
Solubility
Slightly soluble in water; soluble in oils
Miscible at room temperature (in ethanol)
Boiling Point
229.00 to 230.00 °C. @ 760.00 mm Hg
229-230 °C
Melting Point10 - 11 °C
Refractive Index1.585-1.598
Physical Description
Liquid
Pale yellowish oily liquid; powerful, repulsive sulfuraceous odour
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.7% (24 of 1413) of reports.
Warning
H302 (96.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1413 reports by companies from 9 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Furan, 2,2'-[dithiobis(methylene)]bis-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Furan, 2,2'-[dithiobis(methylene)]bis-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (96.2%)
Safety data
- PPE
- Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3334
- hs_code
- 29321900
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationFuran, 2,2'-[dithiobis(methylene)]bis-: ACTIVE
Applications
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.
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.
Preparation methods
PreparationDifurfuryl disulfide is produced from Furfural and Hydrogen sulfide gas.
Upstream & downstream products
Upstream raw materials
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Related reactions
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Compound notes
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