Skip to Content
Merck
CN
All Photos(1)

Documents

Safety Information

153583

Sigma-Aldrich

1-(Trimethylsilyl)imidazole

96%

Synonym(s):

N-Trimethylsilylimidazole, TMSI, TSIM

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Product No.
Description
Pricing

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
K M Höld et al.
Journal of analytical toxicology, 20(6), 345-349 (1996-10-01)
Stanozolol is an anabolic androgenic steroid occasionally abused by athletes. A sensitive, specific, and reproducible method for the quantitative determination of stanozolol in hair has been developed. After the addition of stanozolol-d3 as the internal standard, hair samples (10-25 mg)
Ian Paterson et al.
Angewandte Chemie (International ed. in English), 53(10), 2692-2695 (2014-02-01)
Leiodermatolide is an antimitotic macrolide isolated from the marine sponge Leiodermatium sp. whose potentially novel tubulin-targeting mechanism of action makes it an exciting lead for anticancer drug discovery. In pursuit of a sustainable supply, we report a highly stereocontrolled total
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service