2-(Trimethylsilyl)benzothiazole

• Catalog No.: L11625
• CAS Number: 32137-73-8
• M. F.: C10H13NSSi
• M. W.: 207.36742
• Purity: tech. 90%

SYNONYMS

• Title: 2-(三甲基硅基)苯并噻唑
• IUPAC name: 2-(trimethylsilyl)-1,3-benzothiazole
• IUPAC Traditional name: 2-(trimethylsilyl)-1,3-benzothiazole

DATABASE IDS

• EC Number: 000-000-0
• Beilstein Number: 1073964
• MDL Number: MFCD00068185
• CAS Number: 32137-73-8

PROPERTIES

• Purity: tech. 90%
• Boiling Point: 128-130°C/2mm
• Density: 1.06
• Refractive Index: 1.5720
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否

REFERENCES

• Reacts with electrophiles to give 2-substituted benzothiazoles: J. Heterocycl. Chem., 8, 257 (1971). Reactivity is increased by F^- catalysis; e.g. CsF with aldehydes: Tetrahedron Lett., 23, 5079 (1982). The thiazole ring can be cleaved, so that the reagent behaves as a formyl anion equivalent; see also Benzothiazole, A10380, and 2-(Trimethylsilyl)thiazole, B21903. Unlike 2-lithiobenzothiazole, reaction with a chiral aldehyde can be diastereoselective: Tetrahedron Lett., 26,5477 (1985).
• Reaction with PCl₃, PhPCl₂ or Ph₂PCl gives the corresponding benzothiazolylphosphine: J. Org. Chem., 47, 1489 (1982). With 2-lithiobenzothiazole, 2,2'-bibenzothiazole is formed: Heterocycles, 30, 347 (1990).