Trimethylsilazole, also known as n-Trimethylsilylimidazole, trimethylsilazole, colorless to yellow liquid. Efficient silylation reagents are especially suitable for the synthesis of alcohols and imidazoles, protecting hydroxyl groups in the presence of amino groups. It is an important intermediate for the synthesis of various acyl imidazoles and quinamide; Hydroxyl protected silylation reagent under amine functionalization; Strong silylation reagents, especially alcohols; Synthesis of imide imidazoline. The strongest silylation reagent; It can react with hydroxyl and carboxyl groups quickly and smoothly. It does not react with amine or amide, so it can be used to prepare multiple derivatives of compounds containing both hydroxyl and amino groups. It can be used to silylate sugar in the presence of a small amount of water; When sugar needs to be analyzed as a syrup, it is an ideal choice for silylated sugar. Able to derive most of the steroid hydroxyl groups that are unimpeded and severely hindered.
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C.F |
C6H12N2Si |
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E.M |
140 |
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M.W |
140 |
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m/z |
140 (100.0%), 141 (6.5%), 141 (5.1%), 142 (3.3%) |
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E.A |
C, 51.38; H, 8.62; N, 19.97; Si, 20.02 |
N-Trimethylsilylimidazole commonly used in various chemical synthesis and industrial applications.
N - (Trimethylsilyl) imidazole can be used as a catalyst for many organic reactions, such as methylation, hydroxylation, and aldehyde synthesis reactions.
In many organic synthesis processes, certain functional groups may interfere with the progress of the reaction or affect the purity and stability of the product. In this case, N - (Trimethylsilyl) imidazole can be used as a protective agent to temporarily protect these functional groups to avoid adverse effects on the reaction.
N - (Trimethylsilyl) imidazole also has certain applications in the agricultural field. It can be used as a herbicide and fungicide, effectively removing weeds in farmland and preventing some common plant diseases. In addition, it can also serve as a plant growth regulator to promote plant growth and development.
In drug synthesis, N - (Trimethylsilyl) imidazole can be used as a pharmaceutical intermediate to synthesize some compounds with specific pharmacological effects. For example, it can be used to synthesize some anticancer drugs, antibiotics, analgesics, etc. The synthesized pharmaceutical compounds have specific chemical structures and pharmacological activities, and can be used for the treatment and prevention of various diseases.
In the field of environmental science, N - (Trimethylsilyl) imidazole can be used for the pretreatment and analysis of environmental samples. For example, before conducting chemical analysis on environmental samples such as soil and water, pre-treatment is required to remove interfering substances and extract target compounds. N - (Trimethylsilyl) imidazole can be used as an extractant or adsorbent to effectively extract and enrich target compounds in environmental samples, providing accurate and reliable data for subsequent analysis.
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research experimental case
TSIM has demonstrated its versatility and significance in various chemical reactions and applications, particularly in medicinal and analytical chemistry.
In medicinal chemistry, TSIM has been successfully utilized in the synthesis of aryl-5-arylideneimidazol-4-ones through a dehydration reaction. This reaction is crucial for the preparation of compounds with potential pharmacological activities, making TSIM an invaluable reagent in the drug discovery process. The ability to synthesize these imidazol-4-ones efficiently through a dehydration reaction involving TSIM highlights its relevance in medicinal chemistry and its potential to contribute to the development of new therapeutic agents.
In analytical chemistry, TSIM's application in sterol analysis has proven to be particularly significant. By facilitating rapid GC/MS (gas chromatography/mass spectrometry) analysis, TSIM enables the completion of the sterol analysis process in under 12.5 minutes. This rapid analysis time is crucial for various analytical applications, such as quality control in pharmaceutical manufacturing and forensic analysis, where time-efficient and accurate results are essential. The use of TSIM in sterol analysis not only enhances the speed of the analysis but also maintains the accuracy and reliability of the results, making it a valuable tool in analytical chemistry.
About Sterol analysis
Sterol analysis is a crucial experimental procedure in biochemistry and analytical chemistry, offering insights into the composition and function of sterols in biological samples. Sterols, such as cholesterol, are lipids found in the membranes of animal cells and play vital roles in maintaining cell membrane fluidity, hormone synthesis, and bile acid production.
The sterol analysis experiment typically begins with the extraction of sterols from a biological sample, such as tissue, serum, or plasma. This extraction process involves the use of organic solvents to isolate the sterols from other cellular components. Once extracted, the sterols are often derivatized to enhance their detectability and stability during subsequent analytical steps.
One common method for sterol analysis is gas chromatography/mass spectrometry (GC/MS). In this technique, the derivatized sterols are injected into a gas chromatograph, where they are separated based on their physical properties, such as volatility and polarity. As the sterols elute from the gas chromatograph, they are introduced into a mass spectrometer, which fragments the molecules and measures the mass-to-charge ratios of the resulting fragments. This information is used to identify and quantify the individual sterols in the sample.
Another method for sterol analysis is liquid chromatography/mass spectrometry (LC/MS). This technique offers higher sensitivity and specificity than GC/MS, particularly for the analysis of polar sterols and sterol metabolites. In LC/MS, the sterols are separated based on their interactions with a stationary phase in a liquid chromatograph and then analyzed by mass spectrometry.
The results of sterol analysis experiments can provide valuable information about the sterol composition of a biological sample, which can be used to assess the health status of an individual or to investigate the mechanisms of disease. For example, elevated levels of cholesterol in the blood are associated with an increased risk of cardiovascular disease, while abnormal sterol levels can indicate metabolic disorders or genetic conditions.
Overall, sterol analysis is a powerful experimental tool in biochemistry and analytical chemistry, offering insights into the composition and function of sterols in biological systems.
Synthesis method
TSIM is synthesized through a well-established chemical process that involves the reaction of imidazole with hexamethyldisilazane (HMDS). The synthesis typically begins with the careful selection and preparation of the reactants, ensuring their purity and appropriate stoichiometric ratios.
In a typical synthesis procedure, imidazole is dissolved in an anhydrous solvent, such as tetrahydrofuran (THF) or toluene, under an inert atmosphere to prevent oxidation. Hexamethyldisilazane is then added dropwise to the imidazole solution, while stirring is maintained to ensure thorough mixing. The reaction mixture is heated to a moderate temperature, usually in the range of 50-80°C, to accelerate the reaction rate.
The reaction proceeds through the formation of an intermediate silylated product, which subsequently undergoes rearrangement to yield TSIM. The progress of the reaction is monitored using analytical techniques such as thin-layer chromatography (TLC) or nuclear magnetic resonance (NMR) spectroscopy.
Upon completion of the reaction, the solvent and any unreacted reagents are removed by distillation or evaporation, leaving the crude TSIM product. Purification is then carried out through techniques such as distillation or crystallization to obtain the pure TSIM. This synthesis method provides a straightforward and efficient route to TSIM, making it a readily available reagent for various chemical applications.
Other Features
N-Trimethylsilylimidazole, often abbreviated as TMSImidazole or TMSIm, is a versatile and functional organic compound with a distinct chemical structure featuring an imidazole ring substituted with a trimethylsilyl (TMS) group. This specific substitution pattern provides the molecule with unique properties and reactivity profiles, making it an indispensable reagent in various synthetic chemistry applications.
The imidazole ring itself is known for its ability to participate in hydrogen bonding and coordination chemistry, while the trimethylsilyl group contributes its stabilizing effects and enhances the solubility of TMSImidazole in organic solvents. This combination makes TMSImidazole an excellent base and nucleophile in organic reactions, capable of catalyzing a wide range of transformations.
One of the most notable uses of TMSImidazole is in the field of silicon-based chemistry, where it serves as a key intermediate for the synthesis of silylated compounds. These silylated derivatives are frequently employed in protecting group strategies, facilitating purification processes, and enhancing the stability of sensitive functional groups.
Moreover, TMSImidazole finds application in metal-catalyzed cross-coupling reactions, where it acts as a ligand or activator, promoting efficient coupling of aryl or alkyl halides with organometallic reagents. Its role in these reactions underscores its importance in the synthesis of complex organic molecules, pharmaceuticals, and advanced materials.
In summary, N-Trimethylsilylimidazole is a highly valuable chemical reagent characterized by its unique structure and multifaceted reactivity. Its ability to participate in a broad spectrum of organic reactions makes it a cornerstone in synthetic chemistry, contributing to the development of innovative compounds and technologies across various scientific and industrial domains.
adverse reaction
N-trimethylsilylimidazole (CAS number 18156-74-6, abbreviated as TMS-Imidazole) is an organic silicon compound that appears as a colorless or pale yellow liquid at room temperature. It is hygroscopic and easily reacts with water to form hexamethyldisiloxane (flammable) and imidazole. As an important silanization reagent, TMS Imidazole is widely used in organic synthesis, drug modification, and gas chromatography-mass spectrometry (GC-MS) analysis. However, its chemical properties are active and have certain toxicity, which may cause the following adverse reactions:
- Skin and mucosal irritation: Direct contact can cause redness, blisters, and chemical burns.
- Eye damage: High concentration exposure can cause corneal epithelial detachment and temporary visual impairment.
- Respiratory irritation: Inhalation of vapors or aerosols can cause coughing, wheezing, and laryngeal edema.
- Systemic toxicity: Animal experiments have shown that high doses may damage organs such as the liver and kidneys.
- Environmental toxicity: It has moderate toxicity to aquatic organisms such as fish and algae, and may disrupt ecological balance.
Acute toxic reaction
Oral toxicity
The oral acute toxicity data of TMSI is limited, but based on its chemical structure and toxicity characteristics of similar silanization reagents, it can be inferred that it has moderate toxicity. Animal experiments have shown that intraperitoneal injection of LDLo (minimum lethal dose) in mice is 750 mg/kg, suggesting that oral intake may cause gastrointestinal irritation, central nervous system inhibition, and metabolic disorders. In actual cases, ingestion of TMSI may lead to nausea, vomiting, abdominal pain, and diarrhea, and in severe cases, coma or shock.
Inhalation toxicity
TMSI vapor is highly volatile (boiling point of approximately 100-102 ℃), and inhaling high concentrations of vapor can cause acute respiratory irritation, including coughing, difficulty breathing, chest pain, and laryngeal edema. Animal experiments have shown that mice exposed to TMSI vapor exhibit pulmonary edema and bronchospasm, suggesting that respiratory dysfunction may be caused by direct damage to respiratory mucosa or induction of inflammatory reactions.
Skin contact toxicity
TMSI has a strong irritant effect on the skin, which can cause redness, edema, blisters, and burning sensation upon contact. Skin penetration experiments have shown that TMSI can rapidly penetrate the epidermal barrier, leading to inflammation and cytotoxicity in the dermis. Long term or repeated exposure may cause contact dermatitis, characterized by skin thickening, cracking, and pigmentation.
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