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Sigma-Aldrich

1-(Triisopropylsilyl)pyrrole

95%

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About This Item

Empirical Formula (Hill Notation):
C13H25NSi
CAS Number:
87630-35-1
Molecular Weight:
223.43
MDL number:
MFCD00054932
UNSPSC Code:
12352100
PubChem Substance ID:
24863531
NACRES:
NA.22

Quality Level

100

Assay

95%

form

liquid

refractive index

n20/D 1.492 (lit.)

bp

78 °C/0.4 mmHg (lit.)

density

0.904 g/mL at 25 °C (lit.)

SMILES string

CC(C)[Si](C(C)C)(C(C)C)n1cccc1

InChI

1S/C13H25NSi/c1-11(2)15(12(3)4,13(5)6)14-9-7-8-10-14/h7-13H,1-6H3

InChI key

FBQURXLBJJNDBX-UHFFFAOYSA-N

Related Categories

General description

1-(Triisopropylsilyl)pyrrole (TISP), a heterocyclic building block, is a pyrrole derivative. TISP has been reported to generate pyrrolic cation radicals during cyclovoltammetric studies, via electroreduction. It participates in various electrophilic substitution reactions specifically at β-position, via reaction with various electrophilic reagents (Br+, I+,NO2+,etc).

Application

1-(Triisopropylsilyl)pyrrole may be employed as reagent in perfluoroalkylation and Vilsmeier formylation reactions. It may be used in the preparation of:
  • ethyl 2-(2,4-dinitrophenylhydrazono]-3-[ 1-(triisopropylsily1)-pyrrol-2-yflpropanoate
  • heterocyclic base, 3-nitropyrrole
  • 3-nitropyrrole, required for the synthesis of 1 -(2′-deoxy-β-D-ribofuranosyl)-3-nitropyrrole

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H332 - H319

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

224.6 °F - closed cup

Flash Point(C)

107 °C - closed cup

Certificates of Analysis (COA)

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N-(triisopropylsilyl) pyrrole. A progenitor" par excellence" of 3-substituted pyrroles.
Bray BL, et al.
The Journal of Organic Chemistry, 55(26), 6317-6328 (1990)
Daniel A Harki et al.
Biochemistry, 41(29), 9026-9033 (2002-07-18)
Synthetic small molecules that promote viral mutagenesis represent a promising new class of antiviral therapeutics. Ribavirin is a broad-spectrum antiviral nucleoside whose antiviral mechanism against RNA viruses likely reflects the ability of this compound to introduce mutations into the viral
Observation of the cation radicals of pyrrole and of some substituted pyrroles in fast-scan cyclic voltammetry. Standard potentials and lifetimes.
Andrieux CP, et al.
Journal of the American Chemical Society, 112(6), 2439-2440 (1990)
Reaction of pyrroles with ethyl 2-nitroso-and 2-azo-propenoates, and with ethyl cyanoformate N-oxide: a comparison of the reaction pathways.
Gilchrist TL and Lemos A.
Journal of the Chemical Society. Perkin Transactions 1, 13, 1391-1395 (1993)
Synthesis, Structure, and Deoxyribonucleic Acid Sequencing with a Universal Nucleoside: 1-(2'-Deoxy-. beta.-D-ribofuranosyl)-3-nitropyrrole.
Bergstrom DE, et al.
Journal of the American Chemical Society, 117(4), Synthesis-Synthesis (1999)
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