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Merck

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:
6485-79-6
Molecular Weight:
158.36
NACRES:
NA.22
EC Index Number:
464-880-1
PubChem Substance ID:
24854011
UNSPSC Code:
12352103
MDL number:
MFCD00009657
Beilstein/REAXYS Number:
1733718

Key Documents

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Product Name

Triisopropylsilane, 98%

InChI

1S/C9H22Si/c1-7(2)10(8(3)4)9(5)6/h7-10H,1-6H3

SMILES string

CC(C)[SiH](C(C)C)C(C)C

InChI key

YDJXDYKQMRNUSA-UHFFFAOYSA-N

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.)

Quality Level

200

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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.

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.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

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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Certificates of Analysis (COA)

Lot/Batch Number
SDBB6584
SDBB4124
SDBB3320
SDBB2970
STBL3882

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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)
Kiat Hwa Chan et al.
Scientific reports, 7(1), 12897-12897 (2017-10-12)
Self-assembly of small biomolecules is a prevalent phenomenon that is increasingly being recognised to hold the key to building complex structures from simple monomeric units. Small peptides, in particular ultrashort peptides containing up to seven amino acids, for which our
Transition-metal complex-catalyzed reduction of amides with hydrosilanes: a facile transformation of amides to amines
Mamoru I,et al.
Tetrahedron Letters, 42, 1945-1947 (2001)
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