233781

Triisopropylsilane

98%

• Synonym(s): TIS, Triisopropylhydrosilane, Tris(1-methylethyl)silane
• Linear Formula: [(CH₃)₂CH]₃SiH
• CAS Number: 6485-79-6
• Molecular Weight: 158.36
• Beilstein: 1733718
• MDL number: MFCD00009657
• UNSPSC Code: 12352103
• PubChem Substance ID: 24854011
• EC Index Number: 464-880-1
• NACRES: NA.22

Properties

• Quality Level: 200
• Assay: 98%
• form: liquid
• reaction suitability: reagent type: reductant
• refractive index: n20/D 1.434 (lit.)
• bp: 84-86 °C/35 mmHg (lit.)
• density: 0.773 g/mL at 25 °C (lit.)
• SMILES string: CC(C)[SiH](C(C)C)C(C)C
• InChI: 1S/C9H22Si/c1-7(2)10(8(3)4)9(5)6/h7-10H,1-6H3
• InChI key: YDJXDYKQMRNUSA-UHFFFAOYSA-N

Description

General description

Triisopropylsilane (TIPS) is an organosilicon compound used as a reducing agent in organic synthesis due to its relatively low toxicity, ease of handling, and its ability to selectively reduce various functional groups. It is used in the presence of a Lewis acid such as titanium (IV) chloride to selectively reduce ketones and aldehydes to their corresponding alkanes and selective reduction of epoxides to the corresponding alcohols.

Application

Triisopropylsilane can be used as a reducing agent:

• To synthesize 4-pyrrole phenylacyl peptide during solid-phase peptide synthesis.
• In transition metal complex-catalyzed reaction of amides with hydrosilanes.
• For the selective reduction of C-arylglucosides into β-C-aryl glucosides.
• To facilitate the cleavage of acetamidomethyl (Acm), 4-methoxybenzyl (Mob), and tert-butyl (But) protecting groups from cysteine (Cys) residues in the presence of trifluoroacetic acid.
• For the reduction of amides to corresponding amines in the presence of transition-metal catalysts.

Safety Information

• Pictograms: GHS02
• Signal Word: Warning
• Hazard Statements: H226
• Precautionary Statements: P210 - P233 - P240 - P241 - P242 - P243
• Hazard Classifications: Flam. Liq. 3
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 100.4 °F - closed cup
• Flash Point(C): 38 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves