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Iodotrimethylsilane, chemically known as (CH3)3SiI, is an organosilicon compound that belongs to the broader class of silanes. It is a colorless to yellowish liquid with a pungent odor, characterized by its unique combination of silicon, methyl (CH3) groups, and an iodine (I) atom attached to the silicon center. This compound exhibits both the reactivity of silicon-based compounds and the unique properties imparted by the iodine substituent.
It is a distinct organosilicon compound that falls within the broader category of silanes. Its physical appearance ranges from colorless to a yellowish hue, accompanied by a strong, pungent odor. The unique makeup of this compound lies in its central silicon atom, which is bonded to three methyl (CH3) groups and an iodine (I) atom. This particular combination gives its characteristic properties and reactivity.
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Chemical Formula |
C3H9ISi |
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Exact Mass |
199.95 |
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Molecular Weight |
200.09 |
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m/z |
199.95 (100.0%), 200.95 (5.1%), 201.95 (3.3%), 200.96 (3.2%) |
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Elemental Analysis |
C, 18.01; H, 4.53; I, 63.42; Si, 14.04 |
Products Introduction
It is an efficient reagent for cleaving various functional groups such as ethers, esters, carbamates, ketals, and lactones. It can selectively and efficiently break the C-O bonds in these compounds under mild conditions, often achieving high yields. This makes it a valuable tool in organic synthesis for the deprotection of various protecting groups.
TMSI is commonly used to introduce the trimethylsilyl (TMS) group into organic molecules. For instance, it can react with alcohols (ROH) to form trimethylsilyl ethers (R-OTMS) and hydrogen iodide (HI). This reaction is important in protecting hydroxyl groups during organic synthesis, as TMS ethers are often more stable and easier to handle than the original alcohols.
In the presence of trimethyltin moieties, TMSI can selectively deprotect certain active groups, such as the N-Cbz group. This ability allows chemists to manipulate complex molecules with precision, avoiding unwanted side reactions.
- Recently, TMSI has been reported to convert allyl- and benzylphosphotriesters to their corresponding iodides. This reaction expands the scope of TMSI's applicability in organic synthesis, particularly in the area of phosphorus-containing compounds.
- TMSI has also been used in various other reactions, including the synthesis of silane-based compounds, such as silane subimides, alkyl silanes, and alkenyl silanes. Its Lewis acid properties and reducing abilities make it a valuable reagent in many organic transformations.
In addition to its use in organic synthesis, TMSI can also be employed in gas chromatography analysis. By converting alcohols into silyl ether derivatives, it enhances the volatility of the compounds, making them more suitable for gas chromatography analysis.
Procedure
Preparation of the Reaction Mixture: Trimethylsilyl chloride and sodium iodide are weighed out in a dry, inert atmosphere (e.g., under nitrogen) to prevent moisture or oxygen contamination. The sodium iodide is typically added to the solvent in a round-bottom flask.
Addition of Trimethylsilyl Chloride: Trimethylsilyl chloride is then slowly added to the stirring solution of sodium iodide in the solvent. Care must be taken during this step to avoid vigorous evolution of gas, which can occur due to the exothermic nature of the reaction.
Stirring and Temperature Control: The reaction mixture is stirred for several hours at room temperature or at a slightly elevated temperature (e.g., 50-60°C) if necessary, to ensure complete conversion of the starting materials.
Work-up: After the reaction is complete, the mixture is quenched by adding water or an aqueous solution of an acid (e.g., HCl) to neutralize any remaining base. The product, is then extracted from the aqueous layer using an organic solvent such as diethyl ether or hexane, which is immiscible with water.
Purification: The organic layer containing it is dried over a drying agent (e.g., anhydrous sodium sulfate or magnesium sulfate) to remove any residual water. It is then filtered to remove the drying agent and concentrated under reduced pressure to obtain the pure product.
Storage: It should be stored in a cool, dark place under an inert atmosphere to prevent decomposition and exposure to moisture or air.
Note on Catalysis: While the presence of trace amounts of water or other impurities can catalyze the reaction by promoting the formation of silanol intermediates, this is not always necessary for a successful synthesis. Many practical syntheses proceed smoothly without the need for added catalysts, as the iodide anion itself is a strong nucleophile capable of displacing chloride directly.
Iodotrimethylsilane a variety of hazards
Flammable and explosive
Iodotrimethylsilane is a highly flammable liquid, and its vapor may form explosive mixtures when mixed with air. Therefore, it is necessary to keep away from fire and heat source and avoid static electricity and sparks in the process of use to prevent fire and explosion accidents.
Violent reactivity in contact with water
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Corrosivity
Iodotrimethylsilane is corrosive and may cause serious chemical burns to the skin and eyes. Therefore, it is necessary to wear appropriate protective equipment, such as chemical safety glasses, gas masks, chemical resistant clothing and rubber gloves, etc., to prevent direct contact between the chemical and the skin, eyes, etc., in the process of use.
Health Hazards
Vapors or liquids of Iodotrimethylsilane may cause irritation and damage to the respiratory system, eyes and skin. Prolonged exposure to or inhalation of its vapors may lead to chronic health problems such as respiratory diseases, skin inflammation, etc.
Iodotrimethylsilane may also cause symptoms of poisoning such as nausea, vomiting, headache, dizziness, etc., which may be life-threatening in severe cases.
Environmental hazards
Iodotrimethylsilane may leak into the environment during use and storage, causing contamination of soil, water and ecosystem. Therefore, it is necessary to take appropriate environmental protection measures, such as the construction of anti-leakage facilities, waste water treatment, etc., to minimize the harm to the environment.
Precautions for operation and storage
When operating Iodotrimethylsilane, it is necessary to comply with the operating procedures, ensure that the operation place is well ventilated, and equipped with appropriate fire fighting equipment and leakage emergency treatment equipment.
Applications of Iodotrimethylsilane
► Deprotection in Organic Synthesis
1) Silyl Ether Cleavage
Mechanism: ITMS protonates the silyl ether oxygen, forming a carbocation intermediate that hydrolyzes to the alcohol.
Example: Deprotection of tert-butyldimethylsilyl (TBS) ethers in peptide synthesis.
Advantage: Mild conditions (room temperature, 1–2 hours) and compatibility with acid-sensitive functionalities.
2) Enol Ether and Acetal Cleavage
Application: ITMS hydrolyzes enol ethers (e.g., in vitamin D synthesis) and acetals (e.g., in carbohydrate chemistry).
► Halogenation Reactions
1) Iodination of Alkenes
Mechanism: Anti-addition of iodine across double bonds via a cyclic iodonium intermediate.
Example: Synthesis of vinyl iodides for cross-coupling reactions (e.g., Heck, Suzuki).
Advantage: High regioselectivity and mild conditions compared to iodine (I₂).
2) Chlorination and Bromination
Derivatives: Chlorotrimethylsilane (TMSCl) and bromotrimethylsilane (TMSBr) are used similarly, but ITMS is preferred for iodination.
► Reductive Transformations
1) Sulfoxide Reduction
Mechanism: ITMS reduces sulfoxides to sulfides in the presence of a proton source (e.g., methanol).
Example: Conversion of methyl phenyl sulfoxide to methyl phenyl sulfide.
Advantage: Mild conditions and high yields.
2) Nitro Group Reduction
Application: Reduces nitroarenes to anilines, though tin(II) chloride (SnCl₂) is more common for this purpose.
► Materials Science
1) Polymer Modification
Cross-Linking: ITMS reacts with hydroxyl-terminated polymers (e.g., poly(ethylene glycol)) to form silyl ether cross-links.
Degradation: Controlled cleavage of silyl ethers for stimuli-responsive materials.
2) Silicone Chemistry
Synthesis: ITMS is used to introduce iodine functionalities into silicone polymers for surface modification.
► Pharmaceuticals
1) Drug Synthesis
Example: ITMS is used in the synthesis of atorvastatin (Lipitor) to deprotect silyl ethers in the advanced intermediate.
Advantage: High purity and scalability for GMP production.
2) Radiolabeling
Application: ITMS-mediated iodination of biomolecules for PET imaging (e.g., [¹²³I]-labeled peptides).
Future Perspectives
► Integration with Circular EconomyRecycling: Recovering ITMS from end-of-life polymers via pyrolysis. Example: Degradation of silicone-based materials to reclaim ITMS for reuse. ► Expansion into New MarketsEnergy Storage: ITMS-modified electrolytes for high-voltage lithium-ion batteries. Biomedicine: Antimicrobial coatings for medical devices using ITMS-functionalized polymers. |
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► Digitalization and AutomationAI-Driven Process Optimization: Machine learning models predict reaction outcomes, reducing trial-and-error in synthesis. Example: Real-time monitoring of ITMS-mediated deprotection via inline IR spectroscopy. ► Regulatory and Sustainability DriversGreen Chemistry Certifications: Demand for eco-labeled ITMS derivatives in consumer goods. Carbon Footprint Reduction: Life cycle assessments (LCAs) to minimize emissions in production. |
Iodotrimethylsilane (ITMS) stands as a testament to the power of molecular design in organic synthesis. Its unique reactivity profile-combining mildness with versatility-has enabled breakthroughs in pharmaceuticals, materials science, and beyond. However, the hazardous nature of ITMS demands rigorous safety protocols and sustainable production methods. By embracing circular economy principles, advanced catalysis, and digitalization, the chemical industry can harness the full potential of ITMS while minimizing its ecological footprint. As industries strive for efficiency, safety, and sustainability, ITMS will continue to evolve, shaping the future of chemical synthesis and its impact on global markets. Through collaborative efforts between academia, industry, and regulators, we can ensure that this vital reagent remains a cornerstone of modern chemistry for generations to come.
Iodotrimethylsilane catalytic N ₂ cracking efficiency at 300 ℃/30MPa
Nitrogen (N ₂) is the most abundant gas in the Earth's atmosphere, but its molecular N ≡ N bond has a bond energy of up to 941 kJ/mol and is extremely inactive chemically. In industry, the cracking of N ₂ is mainly achieved through the Haber Bosch process, which uses iron-based catalysts to react N ₂ with H ₂ under high temperature (400-500 ℃) and high pressure (15-30 MPa) conditions to produce ammonia (NH3). However, this process has high energy consumption, carbon emissions amplification, and relies on non renewable resources. Therefore, the development of low-temperature, low-pressure, efficient and environmentally friendly N ₂ cracking catalysts has become a research hotspot in the field of chemistry.
Experimental methods
Pure TMS-I (98% purity) was purchased from Sigma Aldrich and used directly without further purification. To improve stability, some experiments used TMS-I (TMS-I/SiO ₂) loaded with SiO ₂, with a loading amount of 10 wt%. Preparation method: TMS-I is dissolved in anhydrous toluene and mixed with SiO ₂ (specific surface area of 300 m ²/g). After ultrasonic treatment for 2 hours, the solvent is removed by rotary evaporation and dried under vacuum at 100 ℃ for 12 hours.
The reaction is carried out in a high-pressure stainless steel reactor (volume 100 mL) equipped with magnetic stirring and temperature control module. Typical reaction conditions: catalyst: 0.5 g TMS-I or TMS-I/SiO2; Reactants: N ₂ (99.999%) and H ₂ (99.999%), molar ratio 1:3; Temperature: 300 ℃; Pressure: 30 MPa; Time: 24 hours
After the reaction, the gas product was analyzed by gas chromatography (GC, Agilent 7890B), equipped with a TCD detector, and the column temperature was programmed to 50-200 ℃. NH ∝ selectivity is calculated using the following formula:
Among them, N ₂ H ₄ is the byproduct of hydrazine. The conversion rate of N ₂ is calculated by nitrogen balance:
The structure of the catalyst before and after the reaction was analyzed by X-ray diffraction (XRD, Bruker D8 Advance), scanning electron microscopy (SEM, Hitachi SU8010), and X-ray photoelectron spectroscopy (XPS, Thermo Scientific K-Alpha) to investigate the cause of deactivation.
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