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153583

Sigma-Aldrich

1-(Trimethylsilyl)imidazole

96%

Synonym(s):

N-Trimethylsilylimidazole, TMSI, TSIM

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About This Item

Empirical Formula (Hill Notation):
C6H12N2Si
CAS Number:
18156-74-6
Molecular Weight:
140.26
Beilstein:
606148
EC Number:
242-040-3
MDL number:
MFCD00005280
UNSPSC Code:
12352005
PubChem Substance ID:
24849355
NACRES:
NA.22

grade

synthesis grade

Assay

96%

form

liquid

refractive index

n20/D 1.475 (lit.)

bp

93-94 °C/14 mmHg (lit.)

density

0.956 g/mL at 25 °C (lit.)

storage temp.

2-8°C

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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Application

1-(Trimethylsilyl)imidazole (TMSI) was used for derivatization of carbohydrates into trimethylsilyl ethers. It was also used to synthesize polysubstituted chiral spirotetrahydropyrans and as silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.
Silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.

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Description
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Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

42.8 °F - closed cup

Flash Point(C)

6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Maiwenn Jacolot et al.
Organic letters, 14(1), 58-61 (2011-12-02)
We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.
Synthetic Communications, 23, 2191-2191 (1993)
Marijana M Ačanski et al.
Food chemistry, 145, 743-748 (2013-10-17)
Gas chromatography with mass spectrometry was used for carrying out a qualitative analysis of the ethanol soluble flour extract of different types of cereals bread wheat and spelt and pseudocereals (amaranth and buckwheat). TMSI (trimethylsilylimidazole) was used as a reagent
Silylated N,O-ketals from the reaction of ketones with N-trimethylsilylimidazole.
P A Andrews et al.
Journal of chromatography, 419, 271-274 (1987-08-07)
S Kulkarni et al.
Steroids, 53(1-2), 131-147 (1989-01-01)
The reaction of trimethylsilylimidazole (TSIM) and 3-keto-5,10-epoxy-nor-19-methylandrostanone 3 and its 17-acetate analog 4 was examined at two different temperatures. In both compounds, reaction at 90 degrees C gave predominantly a delta 3-silyl-enol ether plus a minor product as a result
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