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153583

Sigma-Aldrich

1-(Trimethylsilyl)imidazole

96%

Sinónimos:

N-Trimethylsilylimidazole, TMSI, TSIM

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About This Item

Fórmula empírica (notación de Hill):
C6H12N2Si
Número de CAS:
18156-74-6
Peso molecular:
140.26
Beilstein/REAXYS Number:
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.

related product

Referencia del producto
Descripción
Precios

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2

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

Certificados de análisis (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
Qin Zhao et al.
Journal of chromatography. A, 1240, 45-51 (2012-04-24)
In the present work, we developed a novel dispersive microextraction technique by combining the advantages of liquid-phase microextraction (LPME) and magnetic solid-phase extraction (MSPE). In this method, trace amount of water directly absorbed on bare Fe₃O₄ to form water-coated Fe₃O₄
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)
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