1-oxo-1λ4-thiolan-1-ium-1-olate

• ChemBase ID: 89548
• Molecular Formular: C4H8O2S
• Molecular Mass: 120.17012
• Monoisotopic Mass: 120.0245005
• SMILES: S1(=O)(=O)CCCC1
• Canonical SMILES: O=S1(=O)CCCC1
• InChI: InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
• InChIKey: HXJUTPCZVOIRIF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-oxo-1λ^4-thiolan-1-ium-1-olate; 1λ^6-thiolane-1,1-dione; 1$l^{6}-thiolane-1,1-dione
• IUPAC Traditional name: 1-oxo-1λ^4-thiolan-1-ium-1-olate; sulfolane
• Synonyms: SULFOLANE; sulfolane; tetramethylene sulfone; Tetrahydrothiophene 1,1-dioxide; Sulfolane; Thiolane 1,1-dioxide; Sulpholane; Tetrahydrothiophene 1,1-dioxide; 四亚甲基砜; 四氢噻吩-1,1-二氧化物; 环丁砜

Database IDs

• CAS Number: 126-33-0
• EC Number: 204-783-1
• MDL Number: MFCD00005484
• Beilstein Number: 107765
• Merck Index: 148955
• PubChem SID: 24900023; 24889157; 162076425
• PubChem CID: 31347
• Chemspider ID: 29080
• Unique Ingredient Identifier: Y5L06AH4G5
• Wikipedia Title: Sulfolane

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.5907958
• LogD (pH = 7.4): -0.5907958
• Log P: -0.5907958
• Molar Refractivity: 27.908 cm^3
• Polarizability: 11.594025 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: miscible in water
• Apperance: clear colorless liquid
• Melting Point: 0-5°C; 20-26 °C(lit.); 25-28°C; 26 - 27°C; 27°C; 27.5 °C
• Boiling Point: 104 °C/0.2 mmHg(lit.); 285 °C(lit.); 285°C; 285 °C; 285°C
• Flash Point: 165 °C; 166°C(330°F); 177 °C; 350.6 °F
• Auto Ignition Point: 528 °C
• Density: 1.212; 1.261; 1.261 g/cm^3, liquid; 1.261 g/ml; 1.261 g/mL at 25 °C(lit.)
• Refractive Index: 1.4825; n20/D 1.484(lit.); n20/D 1.485
• Vapor Pressure: 0.01 mmHg ( 20 °C)
• Vapor Density: 4.2 (vs air)
• Hydrophobicity(logP): -0.984
• Viscosity: 0.01007 Pa·s at 25 °C

Safety Information

• Storage Warning: Harmful/Air Sensitive/Store under Argon; Hygroscopic
• RTECS: XN0700000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22; R:22; R22
• Safety Statements: 25; S:25; S23, S24, S25
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  1

  2
• GHS Hazard statements: H302
• GHS Precautionary statements: P262-P308+P313-P330; P262-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (GC); ≥99.5% (GC); ≥99.8% (GC); 80% w/w aq. soln.; 95%; 99%
• Grade: analytical standard; puriss.; purum
• Impurities: ≤2% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C4H8O2S

DETAILS

Sigma Aldrich - T22209

Packaging
5, 100, 500 g in glass bottle

REFERENCES

• Solvent for nitrations using Nitronium tetrafluoroborate, B20167.
• Solvent for the Baylis-Hillman reaction, using 1,4-Diazabicyclo[2.2.2]octane, A14003, which enables short reaction times at room temperature: Tetrahedron Lett., 45, 1183 (2004).
• High-boiling dipolar aprotic solvent. Compare Dimethyl sulfoxide, A13280, N,N-Dimethylacetamide, A10924 and 1-Methyl-2-pyrrolidinone, A12260.
• Widely used as solvent in the nucleophilic displacement of chloroaromatics with F^- (Halex fluorination). For example, chlorinated benzaldehydes were converted to their fluoro-analogues by heating with KF in tetramethylene sulfone at 220^o: J. Fluorine Chem., 46, 529 (1990). Nitro groups have also been displaced by F^- by heating in the presence of tetramethylammonium chloride and phthaloyl chloride as a nitrite trap: J. Org. Chem., 56, 6406 (1991). See, however, Tetrahydrothiophene 1-oxide, A17502 and Potassium fluoride, 14130.
• Can be doubly metallated at the ɑ-positions with strong bases such as NaNH₂, LiNH₂ or n-BuLi, and the resulting dianion reacted with one or two equivalents of benzophenone to give the mono- or bis-adduct respectively: J. Org. Chem., 35, 1834 (1970); J. Organomet. Chem., 59, 53 (1973). For alkylation of the monolithio-derivative, see: Synth. Commun., 18, 583 (1988).
• Use of this solvent makes possible the reduction of alkyl bromides to alkanes by NaBH₄: Tetrahedron Lett., 3495 (1969).