chlorotris(propan-2-yl)silane

• ChemBase ID: 73448
• Molecular Formular: C9H21ClSi
• Molecular Mass: 192.80154
• Monoisotopic Mass: 192.11010488
• SMILES: [Si](Cl)(C(C)C)(C(C)C)C(C)C
• Canonical SMILES: CC([Si](C(C)C)(C(C)C)Cl)C
• InChI: InChI=1S/C9H21ClSi/c1-7(2)11(10,8(3)4)9(5)6/h7-9H,1-6H3
• InChIKey: KQIADDMXRMTWHZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chlorotris(propan-2-yl)silane
• IUPAC Traditional name: chlorotriisopropylsilane
• Synonyms: Triisopropylsilyl chloride; Chlorotriisopropylsilane; Triisopropylsilyl chloride; Chloro(triisopropyl)silane; Tris(isopropylsilyl) chloride; TIPSCl; Silane IP3; Triisopropylchlorosilane; Triisopropylsilyl chloride; Chlorotriisopropylsilane; 三异丙基氯硅烷; 三异丙氯硅烷; 三异丙基氯甲硅烷; 三异丙氯硅烷; 硅烷 IP3; 三异丙基氯硅烷

Database IDs

• CAS Number: 13154-24-0
• MDL Number: MFCD00009656
• Beilstein Number: 1737446
• PubChem SID: 24889605; 24854324; 24889310; 162038368; 24873800
• PubChem CID: 139400

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.0684
• LogD (pH = 7.4): 4.0684
• Log P: 4.0684
• Molar Refractivity: 50.812 cm^3
• Polarizability: 22.042477 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 198 °C/739 mmHg(lit.); 200°C; 79-80°C/10mm
• Flash Point: 147.2 °F; 62°C; 62°C(144°F); 64 °C
• Density: 0.901 g/mL at 25 °C(lit.); 0.902; 0.908
• Refractive Index: 1.4535; n20/D 1.452(lit.)
• Vapor Pressure: 1.16 mmHg ( 20 °C)

Safety Information

• Storage Warning: Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2987; UN2987
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-27-36/37/39; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318-H227
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2987 8/PG 2

Product Information

• Purity: ≥95.0% (GC); ≥97.0% (GC); 90%; 97%; 97+%
• Grade: produced by Wacker; purum; technical grade
• Linear Formula: [(CH3)2CH]3SiCl

DETAILS

Sigma Aldrich - 90174

Other Notes
prices for bulk quantities on request

Sigma Aldrich - 241725

Application
Use of TIPS substituted alkynes in a preparation of silyl vinyl ketenes from chromium carbene complexes.1
Packaging
10, 50 g in glass bottle

Sigma Aldrich - 92090

Other Notes
Selective silylating agent, useful in nucleotide synthesis (the TIPS group is more stable than the tert-butyldimethylsilyl group against hydrolysis) 1,2,3

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.