18156-74-6

Basic information

• Product Name: N-(Trimethylsilyl)imidazole
• Synonyms: 1-(Trimethylsily)imidazole;1-(trimethylsilyl)-1h-imidazol;1-(trimethylsilyl)-imidazol;1-Imidazolyltrimethylsilane;CT3600;Imidazole, 1-(trimethylsilyl)-;Imidazole, N-(trimethylsilyl)-;N-(Trimethylsilyl)imidazol
• CAS NO: 18156-74-6
• Molecular Formula: C₆H₁₂N₂Si
• Molecular Weight: 140.26
• EINECS: 242-040-3
• Product Categories: 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;Special Silanes;Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C3 to C8;Chemical Synthesis;Heterocyclic Building Blocks;Imidazoles;Silylation Reagents
• Mol File: 18156-74-6.mol

Chemical Properties

• Melting Point: -42 °C
• Boiling Point: 93-94 °C14 mm Hg(lit.)
• Flash Point: 42 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.957 g/mL at 20 °C
• Vapor Pressure: 0.203mmHg at 25°C
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• PKA: 7.96±0.10(Predicted)
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• Stability: Air and Moisture Sensitive
• BRN: 606148
• CAS DataBase Reference: N-(Trimethylsilyl)imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Trimethylsilyl)imidazole(18156-74-6)
• EPA Substance Registry System: N-(Trimethylsilyl)imidazole(18156-74-6)

Safety Data

• Hazard Codes: F,Xi,C
• 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
• TSCA: T
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 18156-74-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless transparent liquid

Physical properties

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

Uses

Different sources of media describe the Uses of 18156-74-6 differently. You can refer to the following data:
1. 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.
2. 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.
3. A general silylating agent, particularly for alcohols. An intermediate for the synthesis of imidazole derivatives.
4. Silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.1

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.

InChI:InChI=1/C6H12N2Si/c1-9(2,3)8-5-4-7-6-8/h4-6H,1-3H3

Upstream product

• 288-32-4 1H-imidazole 
• 75-77-4 chloro-trimethyl-silane 
• 25436-07-1 trimethylsilyl trichloroacetate 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 2857-97-8 trimethylsilyl bromide 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 109-69-3 n-Butyl chloride 
• 124-38-9 carbon dioxide 

Downstream Products

• 109-09-1 2-chloropyridine 
• 372-48-5 2-fluoropyridine 
• 25700-14-5 2-(1H-imidazolyl)pyridine 
• 2846-62-0 (furan-2-ylmethoxy)trimethylsilane 
• 117654-35-0 N-(4-chlorophenyl)-1H-imidazole-1-carboxamide 
• 27363-31-1 1-(phenyl-trimethylsilanyloxy-methyl)-1H-imidazole 
• 10364-94-0 1-benzoylimidazole 
• 33876-94-7 N-phenyl-1H-imidazole-1-carboxamide 
• 62785-90-4 1-ethynyl-1-(trimethylsiloxy)cyclohexane 
• 75-77-4 chloro-trimethyl-silane 
• 16913-98-7 1-(Diethoxyphosphinyl)imidazole 
• 107313-21-3 Imidazol-1-yl-phosphonothioic acid O,O-diethyl ester 
• 67711-52-8 1-(diisopropoxyphosphinyl)imidazole 
• 33876-92-5 N-(4-methoxyphenyl)-1H-imidazole-1-carboxamide 

Relevant articles and documents

Kinetics and mechanism of organocatalytic aza-Michael additions: Direct observation of enamine intermediates

The imidazoles 1a-g add to the CC-double bond of the iminium ion 2 with rate constants as predicted by the equation log k = sN(N + E). Unfavourable proton shifts from the imidazolium unit to the enamine fragment in the adduct 3 account for the failure of imidazoles to take part in iminium-activated aza-Michael additions to enals.

Synthesis and structure of silyl-substituted imidazol-2-ylidenes and their precursors

Previously unknown heterocyclic carbenes and their precursors containing a silicon atom in the side chain were prepared. Their structures were studied by multinuclear 1H, 13C, 15N, and 29Si NMR spectroscopy.

Preparation method of meropenem key intermediate N-trimethylsilylimidazole

The invention provides a preparation method of N-trimethylsilylimidazole. The method comprises the following steps of: 1) under the protection of inert gas, heating imidazole and hexamethyldisilazaneto T1, and carrying out reaction for 1-4h; 2) at the end

Chitosan–silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method

Abstract: The presilylation of purine and pyrimidine nucleobases as well as other related N-heterocycles with HMDS utilizing chitosan–silica sulfate nanohybrid (CSSNH) is described. CSSNH is proved to be a useful, highly efficient and eco-friendly heterogeneous nanohybrid catalyst for silylation of nucleobases. The presilylated nucleobases then underwent the reaction with different sources of carbon electrophiles to afford the desired N-alkyl-substituted derivatives in good-to-excellent yields. CSSNH exhibits several advantageous involving ease of handling and preparation, low cost, reusability and environmental benignity. These unique properties render the CSSNH to be an ideal candidate for use in green industrial processes. Graphic abstract: [Figure not available: see fulltext.].

Preparation method of carbonyl diimidazole

The invention discloses a preparation method of carbonyl diimidazole in the technical field of carbonyl diimidazole synthesis. The preparation method comprises the steps of taking imidazole and hexamethyl disilazane as starting materials, obtaining N-trimethylsilyl imidazole through condensation, absorbing a single byproduct, namely ammonia through a sodium hydroxide solution, allowing N-trimethylsilyl imidazole to react with triphosgene to prepare carbonyl diimidazole, and filtering the principal product, namely carbonyl diimidazole, from liquid trimethylchlorosilane for vacuum drying. A removal step is simpler; the byproduct is gaseous and does not influence purity of the product, namely N-trimethylsilyl imidazole; a reactor with higher purity is provided for a subsequent reaction; in areaction process of N-trimethylsilyl imidazole and triphosgene, no catalyst is required to be added; the method is simple to operate; a byproduct of the reaction of N-trimethylsilyl imidazole and triphosgene is liquid trimethylchlorosilane; and carbonyl diimidazole prepared by the method is higher in purity and good in quality.

Desulfurization of hydrocarbons by ionic liquids and preparation of ionic liquids

The present invention relates to an improved desulfurization process using an ionic liquid compound of general formula C+A?, where C+ represents an organic cation such as alkyl-pyridinium, di-alkyl imidazolium and tri-alkyl imidazolium; and A? is an anion of halides of iron (III), such as, for example, FeCl4?. The desulfurization process is also improved when producing the ionic liquid compound by heating the reactants using microwave energy. The ionic liquids can be used to desulfurize hydrocarbon mixtures by a liquid-liquid extraction.

Unusual course of diazolees silylation and N-siloxycarbonylation

The N-siloxycarbonylation and transamination reactions were studied by an example of diazoles. We found that because of insufficient nucleophilicity of the nitrogen atoms in the first case only the sililylation process occurs, in the second case the low-boiling amine is replaced by the higher boiling one and the process is completed by the formation of O-silyluretans. Pleiades Publishing, Ltd., 2011.

MACROCYCLIC ANTAGONISTS OF THE MOTILIN RECEPTOR FOR TREATMENT OF GASTROINTESTINAL DYSMOTILITY DISORDERS

The present invention provides conformationally-defined macrocyclic compounds that bind to and/or are functional modulators of the motilin receptor including subtypes, isoforms and/or variants thereof. These macrocyclic compounds, at a minimum, possess adequate pharmacological properties to be useful as therapeutics for a range of disease indications. In particular, these compounds are useful for treatment and prevention of disorders characterized by hypermotilinemia and/or gastrointestinal hypermotility, including, but not limited to, diarrhea, cancer treatment-related diarrhea, cancer-induced diarrhea, chemotherapy-induced diarrhea, radiation enteritis, radiation-induced diarrhea, stress-induced diarrhea, chronic diarrhea, AIDS-related diarrhea, C. difficile associated diarrhea, traveller's diarrhea, diarrhea induced by graph versus host disease, other types of diarrhea, dyspepsia, irritable bowel syndrome, chemotherapy-induced nausea and vomiting (emesis) and post-operative nausea and vomiting and functional gastrointestinal disorders. In addition, the compounds possess utility for the treatment of diseases and disorders characterized by poor stomach or intestinal absorption, such as short bowel syndrome, celiac disease and cachexia. The compounds also have use for the treatment of inflammatory diseases and disorders of the gastrointestinal tract, such as inflammatory bowel disease, ulcerative colitis, Crohn's disease and pancreatitis. Accordingly, methods of treating such disorders and pharmaceutical compositions including compounds of the present invention are also provided.

Silica sulfuric acid (SSA) as a highly efficient heterogeneous catalyst for persilylation of purine and pyrimidine nucleobases and other N-heterocycles using HMDS

Purine and pyrimidine nucleobases and other N-heterocycles have been silylated with HMDS in excellent yields in the presence of a catalytic amount of silica sulfuric acid (SSA) as a heterogeneous catalyst. SSA utilizes a shorter reaction time and higher yields of silylated nucleobases. SSA is reusable for several times without a decrease in reactivity or yield of silylated adducts. Copyright

Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies

An efficient silylating system for 1°, 2°, and 3° alcohols, consisting of a silyl chloride/N-methylimidazole/iodine, was developed. Synthetic and mechanistic aspects of this new reagent system, and particularly the role of iodine were investigated in detail using 1H NMR spectroscopy.