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233781

Sigma-Aldrich

Triisopropylsilane

98%

Synonym(s):

TIS, Triisopropylhydrosilane, Tris(1-methylethyl)silane

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About This Item

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

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

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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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Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

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

Certificates of Analysis (COA)

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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)
Tetrahedron Asymmetry, 14, 3243-3247 (2003)
E Gibula-Tarlowska et al.
Behavioural brain research, 372, 112043-112043 (2019-06-22)
Kissorphin (KSO) is a new peptide derived from kisspeptin-10. Previous study has indicated that this peptide displays neuropeptide FF (NPFF)-like anti-opioid activity. Herein, we examined the influence of KSO (1; 3, and 10 nmol, intravenously [i.v.]), on the rewarding action of
Kanicha Sa-ei et al.
Organic letters, 8(20), 4441-4443 (2006-09-22)
The catalytic, diastereoselective coupling of alpha-silyloxy aldehydes and alkynylsilanes catalyzed by a nickel(0) N-heterocyclic carbene complex provides an effective entry to anti-1,2-diols. The scope of couplings and extent of diastereoselection are excellent across a range of substrates.
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