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N-(Trimethylsilyl)imidazole

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CAS:18156-74-6
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CAS:18156-74-6
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N-(Trimethylsilyl)imidazole Basic information
Product Name:N-(Trimethylsilyl)imidazole
Synonyms:N-Trimethylsilylimidazole, 95+%;1-Trimethysiylimidazole;1H-Imidazole, 1-(trimethylsilyl)-;N-TRIMETHYSIYLIMIDAZOLE;1-(Trimethylsily)imidazole;N-TRIMETHYLSILIMIDAZOLE;TIMTEC-BB SBB009056;TRI-SIL Z
CAS:18156-74-6
MF:C6H12N2Si
MW:140.26
EINECS:242-040-3
Product Categories:Silylation Reagents;Analytical Chemistry;GC Derivatizing Reagents;Si (Classes of Silicon Compounds);Silylation (GC Derivatizing Reagents);Silylimidazoles;Si-N Compounds;Trimethylsilylation (GC Derivatizing Reagents);Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C3 to C8;Chemical Synthesis;Heterocyclic Building Blocks;Imidazoles;Special Silanes
Mol File:18156-74-6.mol
N-(Trimethylsilyl)imidazole Structure
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.)
Fp 42 °F
storage temp. Store below +30°C.
solubility Chloroform
form Liquid
pka7.96±0.10(Predicted)
Specific Gravity0.956
color Clear colorless to yellow
Water Solubility decomposes
Sensitive Moisture Sensitive
Hydrolytic Sensitivity7: reacts slowly with moisture/water
BRN 606148
Stability:Air and Moisture Sensitive
InChIKeyYKFRUJSEPGHZFJ-UHFFFAOYSA-N
CAS DataBase Reference18156-74-6(CAS DataBase Reference)
NIST Chemistry Reference1h-Imidazole, 1-(trimethylsilyl)-(18156-74-6)
EPA Substance Registry System1H-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
10-21
Autoignition Temperature540 °C DIN 51794
TSCA T
HazardClass 3
PackingGroup II
HS Code 29332990
MSDS Information
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N-(Trimethylsilyl)imidazole English
SigmaAldrich English
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N-(Trimethylsilyl)imidazole Usage And Synthesis
Chemical PropertiesColorless transparent liquid
Physical propertiesbp 93–94 °C/14 mmHg; fp 5 °C; d 0.956 g cm?3.
UsesN-(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.
UsesN-(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.
UsesSilylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.1
UsesA general silylating agent, particularly for alcohols. An intermediate for the synthesis of imidazole derivatives.
DefinitionChEBI: 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 Description1-(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 suitabilityreagent type: derivatization reagent
reaction type: Silylations
Tag: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

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