tris(propan-2-yl)silane

• ChemBase ID: 147171
• Molecular Formular: C9H22Si
• Molecular Mass: 158.35648
• Monoisotopic Mass: 158.14907724
• SMILES: CC(C)[SiH](C(C)C)C(C)C
• Canonical SMILES: CC([SiH](C(C)C)C(C)C)C
• InChI: InChI=1S/C9H22Si/c1-7(2)10(8(3)4)9(5)6/h7-10H,1-6H3
• InChIKey: YDJXDYKQMRNUSA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(propan-2-yl)silane
• IUPAC Traditional name: triisopropylsilane
• Synonyms: Triisopropylsilane; tris(propan-2-yl)silane; TIS; 三异丙基硅烷

Database IDs

• CAS Number: 6485-79-6
• MDL Number: MFCD00009657
• Beilstein Number: 1733718
• PubChem SID: 24889607; 162241362; 24854011
• PubChem CID: 6327611

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.0698
• LogD (pH = 7.4): 2.0698
• Log P: 2.0698
• Molar Refractivity: 45.2447 cm^3
• Polarizability: 20.272444 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 166°C; 84-86 °C/35 mmHg(lit.)
• Flash Point: 100.4 °F; 35°C(95°F); 38 °C
• Density: 0.773; 0.773 g/mL at 25 °C(lit.)
• Refractive Index: 1.4340; n20/D 1.43; n20/D 1.434(lit.)
• Hydrophobicity(logP): 4.492

Safety Information

• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38
• Safety Statements: 23-26-37-60; 26-36
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥98.0% (GC); 95%; 98%; 99%
• Grade: purum
• Linear Formula: [(CH3)2CH]3SiH

DETAILS

Sigma Aldrich - 233781

Application
The bulky isopropyl groups (vs. ethyl) allow for more selective reductions, e.g., beta-selective reduction of anomeric C-phenyl ketals, but do not diminish their activity (e.g. in the copper triflate catalyzed reductive etherification of trimethylsilyl ethers).
Used in a highly diastereoelective preparation of anti-1,2-diols catalyzed by a Ni(O) N-heterocyclic carbene complex.1
Packaging
10 g in glass bottle
50, 250 g in Sure/Seal™

Sigma Aldrich - 92095

Other Notes
Selective silylation of primary hydroxy groups in the presence of secondary (catalyzed by CsF/imidazole)1

REFERENCES

• Selective silylation of primary OH groups in the presence of secondary has been carried out with this reagent in combination with CsF and imidazole: J. Organomet. Chem., 282, 155 (1985). See Appendix 4.
• Triethylsilane and triisopropylsilane have been studied as cation scavengers in the deprotection of peptides with TFA, and were found to give good results, with triisopropylsilane being particularly effective in trapping trityl cations in the TFA deprotection of cysteine containing peptides. The use of triisopropylsilane minimizes the risk of reduction of the indole nucleus in tryptophan-containing peptides: Tetrahedron Lett., 30, 2739 (1989). See Appendix 6.