N-(Trimethylsilyl)imidazole 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

InChIKey

YKFRUJSEPGHZFJ-UHFFFAOYSA-N

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 

T

HazardClass 

3

PackingGroup 

II

HS Code 

29332990

MSDS

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N-(Trimethylsilyl)imidazole Usage And Synthesis

Chemical Properties

Colorless transparent liquid

Physical properties

bp 93–94 °C/14 mmHg; fp 5 °C; d 0.956 g cm?3.

Uses

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

Uses

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

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

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.

N-(Trimethylsilyl)imidazole(18156-74-6)Related Product Information

• (Trifluoromethyl)trimethylsilane
• Trimethylsilyl cyanide
• TRIMETHYLSILANE
• Potassium trimethylsilanolate
• Hexamethyldisilazane
• 1-Methylimidazole
• Imidazole
• Trimethylsilylacetylene
• Azidotrimethylsilane
• hydroxytrimethylsilane
• N-(Trimethylsilyl)acetamide
• Iodotrimethylsilane
• Pyridine sulfur trioxide
• Chlorotrimethylsilane
• Bromotrimethylsilane
• N-6,9-BIS(TRIMETHYLSILYL)ADENINE
• Silicon
• N-(TRIMETHYL-D9-SILYL)IMIDAZOLE