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1-(Trimethylsilyl)imidazole

for GC derivatization, LiChropur™

Synonym(s):

TSIM, N-Trimethylsilylimidazole, TMSI

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About This Item

Empirical Formula (Hill Notation):
C6H12N2Si
CAS Number:
18156-74-6
Molecular Weight:
140.26
Beilstein/REAXYS Number:
606148
EC Number:
242-040-3
MDL number:
MFCD00005280
UNSPSC Code:
12000000
PubChem Substance ID:
329755874
NACRES:
NA.22

grade

for GC derivatization

Quality Level

100

assay

≥94.0%

quality

LiChropur™

reaction suitability

reagent type: derivatization reagent
reaction type: Silylations

technique(s)

gas chromatography (GC): suitable

refractive index

n20/D 1.475 (lit.)

bp

93-94 °C/14 mmHg (lit.)

density

0.956 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)n1ccnc1

InChI

1S/C6H12N2Si/c1-9(2,3)8-5-4-7-6-8/h4-6H,1-3H3

InChI key

YKFRUJSEPGHZFJ-UHFFFAOYSA-N

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General description

1-(Trimethylsilyl)imidazole (TMSIM) has high silyl donor ability. It does not react with amino groups and also does not help in formation of enol-ether on unprotected ketone groups. It is useful as a silylating agent for ecdysones, norepinephrine, dopamine, steroids, sugars, sugar phosphates and ketose isomers.
Powerful silylating agent, particularly for alcohols; Synthesis of acyl imidazolides

Application

1-(Trimethylsilyl) imidazole may be used for the synthesis an O-silylated derivative of a hexahomotriazacalix[3]arene. It may also be used for the silylation of Ti-MCM-41 catalyst, to study its effect on the olefin epoxidation with aqueous H2O2, 1-(Trimethylsilyl) imidazole was found to improve the hydrophobicity and the catalytic performance of Ti-MCM-41.
Learn more in the Product Information

Other Notes

Reagent for trimethylsilyl and trimethylsilyl ether.

Legal Information

LiChropur is a trademark of Merck KGaA, Darmstadt, Germany

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pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

42.8 °F - closed cup

flash_point_c

6 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Analysis of nanogram quantities of norethisterone in plasma using a GC-MS-COM selective ion detection procedure.
W G Stillwell et al.
Steroids and lipids research, 5(2), 79-90 (1974-01-01)
Synthesis and crystal structure of an O-silylated hexahomotriazacalix [3] arene.
Panadda C
Tetrahedron Letters, 39 (31), 5473-5476 (1998)
Silylation of Ti-MCM-41 by trimethylsilyl-imidazole and its effect on the olefin epoxidation with aqueous H2O2.
Jie Bu and Rhee HK.
Catalysis Letters, 66 (4), 245-249 (2000)
Thomas J. Bruno, Paris D.N. Svoronos,
CRC Handbook of Basic Tables for Chemical Analysis, 111-111 (2010)
Letter: Analysis of bile acids by mass fragmentography -application of 1:1 mixture technique by use of stable isotope labeled compounds.
M Inoue et al.
Chemical & pharmaceutical bulletin, 22(8), 1949-1950 (1974-08-01)
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