ChemicalBook Product Catalog Chemical Reagents Silane reagent N-(Trimethylsilyl)imidazole

N-(Trimethylsilyl)imidazole

Product NameN-(Trimethylsilyl)imidazole
CAS18156-74-6
MFC6H12N2Si
MW140.26
EINECS242-040-3
MOL File18156-74-6.mol

Chemical Properties

Melting point	-42 °C
Boiling point	93-94 °C14 mm Hg(lit.)
Density	0.957 g/mL at 20 °C
refractive index	n20/D 1.475(lit.)
Flash point	42 °F
storage temp.	Store below +30°C.
solubility	Chloroform
form	Liquid
pka	7.96±0.10(Predicted)
Specific Gravity	0.956
color	Clear colorless to yellow
Water Solubility	decomposes
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	7: reacts slowly with moisture/water
BRN	606148
Stability	Air and Moisture Sensitive
InChI	1S/C6H12N2Si/c1-9(2,3)8-5-4-7-6-8/h4-6H,1-3H3
InChIKey	YKFRUJSEPGHZFJ-UHFFFAOYSA-N
SMILES	C[Si](C)(C)n1ccnc1
CAS DataBase Reference	18156-74-6(CAS DataBase Reference)
NIST Chemistry Reference	1h-Imidazole, 1-(trimethylsilyl)-(18156-74-6)
EPA Substance Registry System	1H-Imidazole, 1-(trimethylsilyl)- (18156-74-6)

Safety Information

Hazard Codes	F,Xi,C
Risk Statements	11-36/37/38-14-40-34-37-35-20/21/22
Safety Statements	16-26-33-37/39-45-36/37/39
RIDADR	UN 1993 3/PG 2
WGK Germany	3
RTECS	NI8700000
F	10-21
Autoignition Temperature	540 °C DIN 51794
TSCA	TSCA listed
HazardClass	3
PackingGroup	II
HS Code	29332990
Storage Class	3 - Flammable liquids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Flam. Liq. 2 Skin Irrit. 2

MSDS

Provider	Language
N-(Trimethylsilyl)imidazole	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

Colorless transparent liquid

Physical properties

bp 93–94 °C/14 mmHg; fp 5 °C; d 0.956 g cm3.

Uses

A general silylating agent, particularly for alcohols. An intermediate for the synthesis of imidazole derivatives.

Uses

N-(trimethylsilyl) imidazole (TMSim) is quite reactive with hydroxyl groups in a variety of analytes including a variety of lipids.As with other derivatization reactions,microwave heating can greatly improve process efficiency.

Uses

Silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.1

Uses

N-(Trimethylsilyl)imidazole is a silylating agent for alcohols and 1,3-dicarbonyl compounds; reaction with esters to give imidazolides; preparation of O-trimethylsilyl monothioacetals; aromatization of the A-ring of steroids. It participates in the reactions of Hydroxyl Silylation Reactions, Silyl Aminal Formation Reactions, Nitrogen Silylation Reactions, Acyl Imidazole Formation, Michael Addition Reactions, Substitution Reactions, Phosphoroimidazolidate Formation, and other uses.

Definition

ChEBI: A member of the class of imidazoles in which the hydrogen at position 1 is replaced by a trimethylsilyl group. N-trimethylsilylimidazole is a derivatisation agent used in gas chromatography/mass spectrometry applications.

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.

reaction suitability

reagent type: derivatization reagent
reaction type: Silylations

Preparation Products And Raw materials

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