233781
Triisopropylsilane
98%
Synonym(s):
TIS, Triisopropylhydrosilane, Tris(1-methylethyl)silane
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About This Item
Linear Formula:
[(CH3)2CH]3SiH
CAS Number:
Molecular Weight:
158.36
NACRES:
NA.22
EC Index Number:
464-880-1
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
1733718
Quality Level
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
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.
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signalword
Warning
hcodes
Hazard Classifications
Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
100.4 °F - closed cup
flash_point_c
38 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Tetrahedron Asymmetry, 14, 3243-3247 (2003)
Reduction of a 4-pyrrole phenylacyl-containing peptide with trifluoroacetic acid--triisopropylsilane--phenol--H2O during solid-phase peptide synthesis and its protein kinase C $\alpha$ inhibitory activity
Hwan J and Lee
Bioorganic & medicinal chemistry letters, 15, 2271-2274 (2005)
Tetrahedron Letters, 44, 7837-7840 (2003)