2,5-dihydro-1$l^{6}-thiophene-1,1-dione

• ChemBase ID: 84968
• Molecular Formular: C4H6O2S
• Molecular Mass: 118.15424
• Monoisotopic Mass: 118.00885043
• SMILES: S1(=O)(=O)CC=CC1
• Canonical SMILES: O=S1(=O)CC=CC1
• InChI: InChI=1S/C4H6O2S/c5-7(6)3-1-2-4-7/h1-2H,3-4H2
• InChIKey: MBDNRNMVTZADMQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dihydro-1$l^{6}-thiophene-1,1-dione; 2,5-dihydro-1λ^6-thiophene-1,1-dione
• IUPAC Traditional name: sulfolene
• Synonyms: 2,5-Dihydrothiophene-1,1-dioxide; Butadiene sulfone; 3-Sulfolene; Butadiene sulfone; 3-Sulfolene; Sulfolene; 2,5-dihydro-1H-1lambda~6~-thiophene-1,1-dione; 2,5-dihydrothiophene 1,1-dioxide; BUTADIENE SULFONE; 2,5-二氢噻吩-1,1-二氧化物; 3-环丁烯砜; 丁二烯砜; 3-环丁烯砜; 环丁烯砜

Database IDs

• CAS Number: 77-79-2
• EC Number: 201-059-7
• MDL Number: MFCD00005481
• Beilstein Number: 107004
• Merck Index: 148956
• PubChem SID: 24892071; 24888550; 162072084
• PubChem CID: 6498
• Chemspider ID: 6253
• Wikipedia Title: Sulfolene

CALCULATED PROPERTIES

• Acid pKa: 16.104263
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.6409026
• LogD (pH = 7.4): -0.6409026
• Log P: -0.6409026
• Molar Refractivity: 28.7166 cm^3
• Polarizability: 11.343716 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 63-67°C; 64-67 °C; 65-66 °C; 65-66 °C(lit.)
• Flash Point: 112 °C; 112°C(233°F); 233.6 °F
• Density: 1.314

Safety Information

• RTECS: XM9100000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 41
• Safety Statements: 26-37/39; 26-39; R
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338; P280-P305+P351+P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C4H6O2S

DETAILS

MP Biomedicals - 05215718

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B84505

Packaging
100, 500 g in glass bottle

Sigma Aldrich - 86160

Other Notes
Source of cisoid butadiene for Diels-Alder reactions1,2; Convenient source of sulfur dioxide3

REFERENCES

• Convenient crystalline source of 1,3-butadiene, which is generated on heating to about 110^oC: Rec. Trav. Chim., 61, 785 (1942). For an example of its use in the Diels-Alder reaction, see: Org. Synth. Coll., 6, 454 (1988).
• Also behaves as a dienophile in with reactive dienes, for example 1,3-Diphenylisobenzofuran, L00101: J. Org. Chem., 34, 538 (1969).
• In the presence of Pd(OAc)₂, couples with aryldiazonium fluoroborates to give 3-aryl-4-sulfolenes which are readily isomerized with triethylamine to the 3-aryl-3-sulfolenes, providing a source of the corresponding 2-arylbutadienes: Synth. Commun., 26, 231 (1996).
• Lithiation occurs at the 2-position; subsequent alkylation and thermal extrusion of SO₂ gave a polyene intermediate in a synthesis of the taxane ring system: J. Org. Chem., 62, 2957 (1997).