methyl 1,1-dioxo-2,5-dihydro-1λ6-thiophene-3-carboxylate

• ChemBase ID: 152035
• Molecular Formular: C6H8O4S
• Molecular Mass: 176.19032
• Monoisotopic Mass: 176.01432974
• SMILES: COC(=O)C1=CCS(=O)(=O)C1
• Canonical SMILES: COC(=O)C1=CCS(=O)(=O)C1
• InChI: InChI=1S/C6H8O4S/c1-10-6(7)5-2-3-11(8,9)4-5/h2H,3-4H2,1H3
• InChIKey: YHHZABJZHHCDNW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 1,1-dioxo-2,5-dihydro-1λ^6-thiophene-3-carboxylate
• IUPAC Traditional name: methyl 1,1-dioxo-2,5-dihydro-1λ^6-thiophene-3-carboxylate
• Synonyms: 3-Carbomethoxy-3-sulfolene; 3-Methoxycarbonyl-3-sulfolene; 3-Methoxycarbonyl-2,5-dihydrothiophene-1,1-dioxide; 3-Methoxycarbonyl-3-sulfolene; Methyl 3-sulfolene-3-carboxylate; 3-甲氧基羰基-3-亚砜; 3-甲氧羰基-2,5-二氢噻吩-1,1-二氧化物; 3-甲氧基羰基-3-亚砜; 3-环丁烯砜-3-甲酸甲酯

Database IDs

• CAS Number: 67488-50-0
• EC Number: 266-700-5
• MDL Number: MFCD00042754
• Beilstein Number: 1368581
• PubChem SID: 24883658; 162246181
• PubChem CID: 368979

CALCULATED PROPERTIES

• Acid pKa: 12.740401
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.82662135
• LogD (pH = 7.4): -0.8266233
• Log P: -0.8266213
• Molar Refractivity: 39.4849 cm^3
• Polarizability: 15.88789 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 60-62 °C; 60-64°C

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (S); 98%
• Empirical Formula (Hill Notation): C6H8O4S

DETAILS

Sigma Aldrich - 64945

Other Notes
A stable precursor of 2-methoxycarbonyl-1,3-butadiene, useful for cycloadditions1
Packaging
1 g in glass bottle

REFERENCES

• Precursor of 2-methoxycarbonyl-1,3-butadiene (cf 3-Sulfolene, A13887), useful in cycloaddition reactions: J. Org. Chem., 43, 4431 (1978).