2,5-Dihydrothiophene 1,1-dioxide

HCID 6498CAS 20966-34-1

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Basic information

Standard SMILES: O=S1(=O)CC=CC1
InChIKey: MBDNRNMVTZADMQ-UHFFFAOYSA-N
Molecular formula: C4H6O2S
Average molar mass: 118.157 g/mol
Monoisotopic mass: 118.00885043

Names & identifiers

Preferred name: 2,5-Dihydrothiophene 1,1-dioxide
IUPAC: 2,5-Dihydro-1H-1lambda~6~-thiophene-1,1-dione
English name: 3-Sulfolene
Molecular formula: C4H6O2S
Molecular weight: 118.15

Names & synonyms

BUTADIENE SULFONESULFOLENE2,5-DIHYDROTHIOPHENE-1,1-DIOXIDESulfol-3-enebeta-SulfoleneNCI-C045573-Sulfolene3-SULPHOLENE3-Sulfolene,98%3-Sulfolene >

Database identifiers

CAS: 20966-34-1、28452-93-9、77-79-2
PubChem CID: 6498
DTXSID: DTXSID6021294
ChEMBL: CHEMBL3182104
ChEBI: CHEBI:194619
UNII: Z6003L44MN
EC Number: 201-059-7、693-220-7

Properties

Physicochemical properties

Melting point: 65 · 65-66 °C(lit.)
Boiling point: 190.71 °C · 190.71°C (rough estimate)
bulk density: 840 kg/m3 · 840kg/m3
Density: 1.3 · 1.3
refractive index: 1.4765 · 1.4765 (estimate)
Flash point: 230 °F · >230 °F
storage temp.: 30 °C · Store below +30°C.
solubility: 130 g/l · 130g/l
form: Powder
color: Yellow to orange or light brown
Water Solubility: Soluble in water, ethanol, benzene, ether.
Merck: 14 · 14,8956
BRN: 107004 · 107004
Henry's Law Constant: 2.3 · 2.3×100 mol/(m3Pa) at 25℃, HSDB (2015)
Stability: Stable, but decomposes above the melting point. Combustible. Incompatible with strong oxidizing agents.
InChI: 1S/C4H6O2S/c5-7(6)3-1-2-4-7/h1-2H,3-4H2
InChIKey: MBDNRNMVTZADMQ-UHFFFAOYSA-N
SMILES: O=S1(=O)CC=CC1
Toxicology and Carcinogenesis: 3 · Bioassay of 3-Sulfolene for Possible Carcinogenicity (CASRN 77-79-2)
CAS DataBase Reference: 77 · 77-79-2(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 6003 L44MN · Z6003L44MN
EPA Substance Registry System: 3 · 3-Sulfolene (77-79-2)
UNSPSC Code: 12352119 · 12352119
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 319 · H319
Precautionary statements: 264 · P264-P280-P305+P351+P338-P337+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 41 · 41
Safety Statements: 26 · 26-37/39
RIDADR: 3335 · UN 3335
WGK Germany: 1 · 1
RTECS: 9100000 · XM9100000
TSCA: TSCA listed
HS Code: 2934 · 2934 99 90
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 · Eye Irrit. 2
Hazardous Substances Data: 77 · 77-79-2(Hazardous Substances Data)
Toxicity: 50 orally · LD50 orally in Rabbit: 2547 mg/kg LD50 dermal Rabbit > 5000 mg/kg

Safety & regulation

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 1
tsca: TSCA listed
rtecs: XM9100000
ridadr: UN 3335
hs_code: 2934 99 90
Toxicity: LD50 orally in Rabbit: 2547 mg/kg LD50 dermal Rabbit > 5000 mg/kg
risk_code: 41
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-37/39
Storage Class: 11 - Combustible Solids
Hazard statements: H319
Hazard Classifications: Eye Irrit. 2
Precautionary statements: P264-P280-P305+P351+P338-P337+P313
Hazardous Substances Data: 77-79-2(Hazardous Substances Data)

Chemistry & industry

Applications

Uses3-SULFOLENE was used in the isomerization of isoprene rubber. Sulfolene is also an analytical reagent used in the investigation of role of adducts in protein supercharging with sulfolane.

UsesIt is a source of cisoid butadiene for Diels-Alder reactions. This chemical is also a convenient source of sulfur dioxide. It is a solvent used in the petrochemical industry for the extraction of aromatics from hydrocarbon streams.