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Chloro(methyl)diphenylsilane

Catalog No. L04162 Name Alfa Aesar
CAS Number 144-79-6 Website
M. F. C13H13ClSi Telephone
M. W. 232.78082 Fax
Purity 97% Email
Storage Chembase ID: 150339

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 Pictograms GHS05
GHS Hazard statements H314-H318
European Hazard Symbols Corrosive 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
Hazard Class 8
UN Number UN2987
Packing Group II

DETAILS

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).