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| | N-(Trimethylsilyl)imidazole Basic information | | Synthesis |
| | 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 | | 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) |
| 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 |
| | N-(Trimethylsilyl)imidazole Usage And Synthesis |
| Synthesis | Add the appropriate amount of imidazole (1 mmol), chitosan sulfate nanoparticles (0.05 g), and hexamethyldisilazane (10 mL) to a dry round-bottom flask (50 mL). Heat the resulting reaction mixture to 90 °C and stir at this temperature for 7 minutes until a clear liquid is obtained. After the reaction is complete, filter the reaction mixture directly to remove the catalyst. Concentrate the filtrate under vacuum and evaporate the filtrate to obtain the target product, N-(Trimethylsilyl)imidazole.  | | 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 | 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. | | reaction suitability | reagent type: derivatization reagent
reaction type: Silylations |
| | N-(Trimethylsilyl)imidazole Preparation Products And Raw materials |
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