tert-Butyldiphenylchlorosilane

• Catalog No.: A12721
• CAS Number: 58479-61-1
• M. F.: C16H19ClSi
• M. W.: 274.86056
• Purity: 97%

SYNONYMS

• Title: 叔丁基二苯基氯硅烷
• IUPAC name: tert-butyl(chloro)diphenylsilane
• IUPAC Traditional name: tert-butyl(chloro)diphenylsilane
• Synonyms: tert-Butyldiphenylsilyl chloride; tert-Butylchlorodiphenylsilane

DATABASE IDS

• CAS Number: 58479-61-1
• MDL Number: MFCD00000497
• EC Number: 261-282-0
• Beilstein Number: 644023

PROPERTIES

• Purity: 97%
• Boiling Point: 90-92°C/0.01mm
• Density: 1.072
• Flash Point: 112°C(233°F)
• Refractive Index: 1.5680
• 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 the formation, with e.g. imidazole, of t-butyldiphenylsilyl (TBDPS) ethers of alcohols: Can. J. Chem., 53, 2975 (1975); Org. Synth. Coll., 9, 139 (1998). Alternative to tert-Butyldimethylchlorosilane, A13064, allowing selective protection of primary alcohols in the presence of secondary, using DMAP/pyridine: Helv. Chim. Acta, 69, 1273 (1986), or DMAP/triethylamine: Tetrahedron Lett., 99 (1979); 26, 1185 (1985). TBDPS ethers tend to be more crystalline and are much more stable to acidic conditions than TBDMS. They can also survive acetal formation and cleavage, as well as the acidic conditions required for cleavage of trityl and THP ethers. Silylation rates of hindered alcohols have been increased in the presence of silver nitrate: J. Am. Chem. Soc., 116, 5050 (1994).
• Cleavage occurs readily with TBAF in THF: Org. Synth. Coll., 9, 4 (1998). For use of K10 clay in aqueous MeOH, see: J. Org. Chem., 61, 9026 (1996). Cleavage with BBr₃ leads directly to the corresponding alkyl bromides: J. Org. Chem., 53, 3111 (1988).
• The silyl copper species derived from the lithio-derivative and CuCN adds to terminal alkynes, giving vinyl copper intermediates which react with electrophiles to give vinyl silanes. The presence of the hindered TBDPS group confers some useful differences in comparison with less hindered silyl groups: J .Chem. Soc., Perkin 1., 1525 (1995); compare Chlorodimethylphenylsilane, A15638. The hindered TBDPS group has also been utilized in the Peterson olefination reaction to promote high (Z)-selectivity: Synthesis, 1223 (2000).