tert-Butyldimethylchlorosilane

• Catalog No.: A13064
• CAS Number: 18162-48-6
• M. F.: C6H15ClSi
• M. W.: 150.7218
• Purity: 97%

SYNONYMS

• Title: 叔丁基二甲基氯硅烷
• IUPAC name: tert-butyl(chloro)dimethylsilane
• IUPAC Traditional name: t-butyldimethylchlorosilane
• Synonyms: tert-Butyldimethylsilyl chloride; tert-Butylchlorodimethylsilane

DATABASE IDS

• EC Number: 242-042-4
• CAS Number: 18162-48-6
• MDL Number: MFCD00000501
• Beilstein Number: 505999

PROPERTIES

• Purity: 97%
• Boiling Point: 124-126°C
• Density: 0.81
• Flash Point: 22°C(72°F)
• Melting Point: 86-89°C
• GHS Hazard statements: H228-H314-H318
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P280-P305+P351+P338-P309-P310
• Risk Statements: 11-34
• RTECS: VV2000000
• Safety Statements: 16-26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 4.1
• UN Number: UN2925
• Packing Group: II

REFERENCES

• Reagent for silylation of hydroxyl functions (see Appendix 4), giving silyl ethers more stable to aqueous hydrolysis e.g. during work-up, than TMS. Various conditions have been used for the introduction of the group:
• Imidazole in DMF: J. Am. Chem. Soc., 94, 6190 (1972); Et₃N - DMAP: Tetrahedron Lett., 99 (1979); Org. Synth. Coll., 9, 136 (1998); N-ethyldiisopropylamine: Tetrahedron Lett., 25, 227 (1984); 1,1,3,3-tetramethylguanidine: J. Org. Chem., 49, 4657 (1984); K₂CO₃ (phase-transfer): Synth. Commun., 11, 545 (1981); DBU - superior to imidazole for thiols, amines and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).
• Cleavage is generally effected with fluoride ion e.g. TBAF in an aprotic system: J. Am. Chem. Soc., 94, 6190 (1972), or KF with a phase-transfer catalyst: J. Am. Chem. Soc., 90, 4462, 4464 (1968); 96, 2250 (1974); J. Chem. Soc., Chem. Commun., 514 (1979).
• Acidic ion-exchange resin: Tetrahedron Lett., 21, 137 (1980); NBS in DMSO: Synthesis, 234 (1980); BF₃ etherate: Synth. Commun., 9, 295 (1979); FeCl₃ or SnCl₂ in acetonitrile: Synth. Commun., 20, 757 (1990); K 10 clay in aqueous methanol: J. Org. Chem.61, 9026 (1996); DMSO-water at 90^o; many other groups unaffected: Tetrahedron Lett., 38, 495 (1997). See also Pyridinium p-toluenesulfonate, A15708, and Triethylamine trihydrofluoride, L14417.
• Many other reagents have been used, including: