trimethylsulfanium iodide

• ChemBase编号: 52564
• 分子式: C3H9IS
• 平均质量: 204.07303
• 单一同位素质量: 203.94696929
• SMILES: [S+](C)(C)C.[I-]
• Canonical SMILES: C[S+](C)C.[I-]
• InChI: InChI=1S/C3H9S.HI/c1-4(2)3;/h1-3H3;1H/q+1;/p-1
• InChIKey: VFJYIHQDILEQNR-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: trimethylsulfanium iodide
• IUPAC传统名: trimethylsulfonium iodide
• 别名: 三甲基碘化锍; Trimethylsulfonium iodide; Trimethylsulfonium iodide

登记号

• CAS号: 2181-42-2
• EC号: 218-555-4
• MDL号: MFCD00011632
• Beilstein号: 3555192
• PubChem SID: 162057327; 24900497
• PubChem CID: 75127

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): -0.07723071
• LogD (pH = 7.4): -0.07723071
• Log P: -0.07723071
• 摩尔折射率: 22.4031 cm^3
• 极化性: 9.693327 Å^3
• 极化表面积: 0.0 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

• 熔点: 213°C(sub); 215-220 °C(lit.); ca 215°C subl.

安全信息

• 保存注意事项: IRRITANT; Light Sensitive
• RTECS编号: WR8750000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: false; 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥98.0% (AT); 98%; 99%
• 级别: purum
• 线性分子式: (CH3)3S(I)

详细说明

Sigma Aldrich - T80489

包装
25, 100 g in poly bottle
Application
用强碱处理可生成二甲基亚甲基锍，而后又可参与酮的羰基原位反应形成环氧化物1或烯丙醇。2

Sigma Aldrich - 92762

Other Notes
二甲基亚甲基锍的前体（亚甲基转移试剂）1,2；将羰基化合物转化为环氧化物或烯丙醇3,4,5

参考文献

• Methylene transfer to imines and arylhydrazones gives aziridines and N-arylaminoaziridines respectively: Synthesis, 330 (1983).
• The ylide, generated with strong base, is a powerful methylene transfer reagent, converting aldehydes and ketones to epoxides; reaction with ɑ?-enones also gives epoxides (contrast Trimethylsulfoxonium iodide, A14589): J. Am. Chem. Soc., 87, 1353 (1965):
  
• Other conditions for addition to aldehydes include: phase-transfer catalysis: Angew. Chem. Int. Ed., 12, 845 (1973), KOH in acetonitrile: Tetrahedron Lett., 23, 5283 (1982), or KF on alumina: Tetrahedron, 41, 1259 (1985). With aryl aldehydes, the use of KO-t-Bu gives improved results by suppressing the competing Cannizzaro reaction: Org. Prep. Proced. Int., 27, 219 (1995). A simplified, solvent-free method employing KO-t-Bu has been reported for ketones: Heterocycles, 46, 185 (1997). With excess of the sulfonium ylide, ketones or epoxides give good yields of allylic alcohols, whereas aldehydes give poor yields. Under similar conditions, the sulfoxonium ylide gives oxetanes: Tetrahedron Lett., 35, 2009, 5449 (1994).
• Addition to vinyl sulfones gives cyclopropyl sulfones: J. Org. Chem., 29, 3277 (1964). Similarly, vinylsulfonates and sulfonamides give cyclopropanes in fair to good yields: J. Org. Chem., 33, 3849 (1968).
• Methylene transfer to allylic, propargylic, benzylic and primary alkyl halides and sulfonates results in formation of terminal alkenes in generally good yields: Tetrahedron Lett., 35, 5453 (1994).
• Reaction with Ag₂O gives the corresponding hydroxide, which is a useful methylating agent for various functional groups, including carboxylic acids, phenols, thiols and N-heterocycles: J. Org. Chem., 44, 638 (1979). Both the iodide and the hydroxide have been used for the methylation of pyrimidine nucleosides; see, e.g.: J. Chem. Soc., Perkin 1, 13 (1989).