Chlorotriisopropylsilane

• Catalog No.: A17376
• CAS Number: 13154-24-0
• M. F.: C9H21ClSi
• M. W.: 192.80154
• Purity: 97+%

SYNONYMS

• Title: 三异丙基氯硅烷
• IUPAC name: chlorotris(propan-2-yl)silane
• IUPAC Traditional name: chlorotriisopropylsilane
• Synonyms: Triisopropylchlorosilane; TIPSCl

DATABASE IDS

• CAS Number: 13154-24-0
• MDL Number: MFCD00009656
• Beilstein Number: 1737446

PROPERTIES

• Purity: 97+%
• Boiling Point: 200°C
• Density: 0.908
• Flash Point: 62°C(144°F)
• Refractive Index: 1.4535
• GHS Hazard statements: H314-H318-H227
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN2987
• Packing Group: II

REFERENCES

• Reagent for the protection of alcohols as triisopropylsilyl (TIPS) ethers. See Appendix 4. Methods of introduction include imidazole in DMF: Tetrahedron Lett., 2865 (1974), or imidazole/DMAP: Chem. Lett., 41 (1987). Also useful for N-protection. The steric bulk of TIPS makes it useful as a regio- and stereodirecting group, allowing selective protection of primary hydroxyl in the presence of secondary: Tetrahedron Lett., 2865 (1974). TIPS ethers are more resistant to acidic hydrolysis than TBDMS ethers, but less so than tert-butyldiphenylsilyl (TBDPS) ethers. However, they are more resistant to basic hydrolysis than either TBDMS or TBDPS derivatives: J. Org. Chem., 45, 4797 (1980); 49, 3239 (1984); Tetrahedron Lett., 24, 3455 (1983).
• Cleavage is usually accomplished by treatment with F^-: J. Org. Chem., 51, 4941 (1986); see Tetra-n-butylammonium fluoride, A10588. Alternative methods include dilute HCl: Tetrahedron Lett., 2865 (1974), or 80% AcOH: J. Carbohydr., Nucleosides, Nucleotides, 3, 197 (1976).
• For a comprehensive review of the TIPS group in organic chemistry, see: Chem. Rev., 95, 1009 (1995). See also Triisopropylsilyl trifluoromethanesulfonate, B21127.