Chloro(methyl)diphenylsilane

• Catalog No.: L04162
• CAS Number: 144-79-6
• M. F.: C13H13ClSi
• M. W.: 232.78082
• Purity: 97%

SYNONYMS

• Title: 二苯基甲基氯硅烷
• IUPAC name: chloro(methyl)diphenylsilane
• IUPAC Traditional name: silane, chloromethyldiphenyl-
• Synonyms: Diphenylmethylchlorosilane; Chlorodiphenylmethylsilane

DATABASE IDS

• Beilstein Number: 2937445
• CAS Number: 144-79-6
• EC Number: 205-639-0
• MDL Number: MFCD00000498

PROPERTIES

• Purity: 97%
• Boiling Point: 294-295°C
• Density: 1.104
• Flash Point: 141°C(285°F)
• Refractive Index: 1.5740
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2987
• Packing Group: II

REFERENCES

• Silylating agent (see Appendix 4) for formation, in the presence of a base such as imidazole in DMF, of DPMS ethers, intermediate in hydrolytic stabilty between TMS and TBDMS. DPMS ethers are incompatible with acid, base, BuLi, Cr(VI) oxidants and LIAlH₄, but stable to silica chromatography: J. Org. Chem., 52, 165 (1987). They can be cleaved with mild acid or base, or F^-. Selective cleavage in high yield in the presence of TBDMS or TBDPS ethers with NaN₃ in DMF was reported: J. Chem. Soc., Chem. Commun., 381 (1989).
• In reactions with lithiated esters and lactones C-silylation predominates. The resulting ɑ-DPMS esters behave as vinyl dication equivalents: J. Am. Chem. Soc., 103, 2418 (1981); Pure Appl. Chem., 62, 2021 (1990), useful precursors of, e.g.: terminal alkenes: Synth. Commun., 13, 1163 (1983); 1,1-disubstituted alkenes: Tetrahedron Lett., 23, 271 (1982); Org. Synth. Coll., 8, 474 (1993); ?-keto silanes and ketones: J. Org. Chem., 50, 5260 (1985); 58, 2718 (1993):
  
• TBDMS esters react with aldehydes and ketones to give ?-hydroxy silanes, which undergo Peterson elimination to ɑ-substituted ɑ?-unsaturated esters: J. Org. Chem., 49, 3385 (1984).