Chlorotrimethylsilane

• Catalog No.: A13651
• CAS Number: 75-77-4
• M. F.: C3H9ClSi
• M. W.: 108.64206
• Purity: 98+%

SYNONYMS

• Title: 三甲基氯硅烷
• IUPAC name: chlorotrimethylsilane
• IUPAC Traditional name: chlorotrimethylsilane
• Synonyms: Trimethylchlorosilane; TMS chloride

DATABASE IDS

• EC Number: 200-900-5
• Beilstein Number: 1209232
• CAS Number: 75-77-4
• MDL Number: MFCD00000502

PROPERTIES

• Purity: 98+%
• Boiling Point: 56-58°C
• Density: 0.856
• Flash Point: -27°C(-16°F)
• Melting Point: -58°C
• Refractive Index: 1.3887
• GHS Hazard statements: H225-H311-H314-H318
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P303+P361+P353-P305+P351+P338-P361-P405-P501A
• Risk Statements: 11-14-21-34
• RTECS: VV2710000
• Safety Statements: 8-16-26-30-36/37/39-45-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1298
• Packing Group: II

REFERENCES

• For facile O-silylation of tertiary alcohols in the presence of Mg metal, see: Synlett, 1025 (2000).
• Carbonyl compounds can be converted to their silyl enol ethers, e.g. with triethylamine in DMF: Org. Synth. Coll., 6, 327 (1988); 7,424 (1990); 8, 460 (1993); or using catalysis with NaI: Org. Synth. Coll., 9, 573 (1998).
• Conjugated enones give trimethylsilyloxydienes. For examples, see: Org. Synth. Coll., 6, 445 (1988); 7, 282 (1990). TMS chloride, LiBr and trimethylamine in THF is a convenient system for silylation of enones: Acta Chem. Scand., 43, 188 (1989). The same combination converts ɑ- and ?-diketones to their bis silyl enol ethers: Acta Chem. Scand., 43, 304 (1989). See also Trimethylsilyl trifluoromethanesulfonate, A12535.
• The conversion of alcohols to alkyl chlorides requires catalysis, e.g. SeO₂: J. Org. Chem., 53, 3634 (1988), or by DMSO: J. Org. Chem., 60, 2638 (1995). The same system is also effective in opening epoxides.
• For cleavage of ethers, see Sodium iodide, A15480.
• Silylation at carbon atoms is usually carried out using organometallic reagents, e.g. vinylmagnesium bromide: Org. Synth. Coll., 6, 1033 (1988). In aromatic rings, silyl groups can be introduced by directed metallation, followed by silylation; see e.g.: J. Org. Chem., 49, 4657 (1989). The silyl substituents can readily be replaced by electrophiles, allowing "abnormal" patterns of substitution. See 1,3-Dimethoxybenzene, A13380.
• For further details and reviews, see Appendix 4.