1-oxo-1λ4-thiolan-1-ium-1-olate

• ChemBase编号: 89548
• 分子式: C4H8O2S
• 平均质量: 120.17012
• 单一同位素质量: 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

名称和登记号

名称

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

登记号

• CAS号: 126-33-0
• EC号: 204-783-1
• MDL号: MFCD00005484
• Beilstein号: 107765
• 默克索引号: 148955
• PubChem SID: 24889157; 162076425; 24900023
• PubChem CID: 31347
• Chemspider ID: 29080
• 美国药典/FDA物质标识码: Y5L06AH4G5
• 维基百科标题: Sulfolane

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.5907958
• LogD (pH = 7.4): -0.5907958
• Log P: -0.5907958
• 摩尔折射率: 27.908 cm^3
• 极化性: 11.594025 Å^3
• 极化表面积: 34.14 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: miscible in water
• 外观: clear colorless liquid
• 熔点: 0-5°C; 20-26 °C(lit.); 25-28°C; 26 - 27°C; 27°C; 27.5 °C
• 沸点: 104 °C/0.2 mmHg(lit.); 285 °C(lit.); 285°C; 285 °C; 285°C
• 闪点: 165 °C; 166°C(330°F); 177 °C; 350.6 °F
• 自燃点: 528 °C
• 密度: 1.212; 1.261; 1.261 g/cm^3, liquid; 1.261 g/ml; 1.261 g/mL at 25 °C(lit.)
• 折射率: 1.4825; n20/D 1.484(lit.); n20/D 1.485
• 蒸汽压: 0.01 mmHg ( 20 °C)
• 蒸汽密度: 4.2 (vs air)
• 疏水性(logP): -0.984
• 粘度: 0.01007 Pa·s at 25 °C

安全信息

• 保存注意事项: Harmful/Air Sensitive/Store under Argon; Hygroscopic
• RTECS编号: XN0700000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22; R:22; R22
• 安全公开号: 25; S:25; S23, S24, S25
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• NFPA704:
  

  1

  2
• GHS危险声明: H302
• GHS警示性声明: P262-P308+P313-P330; P262-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

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

详细说明

Sigma Aldrich - T22209

包装
5, 100, 500 g in glass bottle

参考文献

• 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).