Related Attributes
Product details
Trimethylsilyl powder is white odourless crystals, need to be closed at room temperature, cool, ventilated and dry inert gas storage, flammable, avoid direct contact, Trimethylsilyl CAS 13435-12-6 is a kind of chemical intermediates, keep away from oxides, and sources of ignition.
Functions of Trimethylsilyl powder
1. Protective groups
Hydroxyl protection: reacts with alcohol/phenol to generate stable silyl ethers to avoid sensitive functional groups being destroyed during the reaction.
Carboxyl protection: protect carboxylic acids by silyl esterification to improve reaction selectivity.
2. Activation and catalysis
Lewis acid catalysis: such as trimethylsilyl trifluoromethanesulfonate (TMSOTf), which can catalyze the formation of enol silyl ethers and carbon cation reactions.
Cyanation reaction: TMSCN is used as a mild cyanation reagent for the synthesis of cyanohydrins of aldehydes and ketones.
3. Functional transformation
Trifluoromethylation: (TMSCF₃) is used as a nucleophilic trifluoromethylation reagent for drug molecule modification (such as antiviral peptides, hormone regulators).
Free radical reaction: trisilane (trimethylsilyl) is used as a reducing agent to participate in carbon-halogen bond cleavage and carbonyl hydrogenation.
4. Other applications
Azide synthesis: used to construct metal heteronuclear complexes and spirocyclic tetrazolyl compounds.
Surface treatment: silicon-based compounds are used for material modification
Application of Trimethylsilyl in Drug Synthesis
1. Functional group protection
Hydroxyl protection: Protect alcohol/phenolic hydroxyl groups by forming stable silyl ethers to prevent them from being destroyed in subsequent reactions, which is often used in the synthesis of antibiotics (such as ceftazidime).
Carboxyl protection: Silylation protects carboxylic acids to improve the reaction selectivity of sensitive functional groups in drug molecules.
2. Catalysis and activation
Strong Lewis acid catalysis: Trimethylsilyl trifluoromethanesulfonate (TMSOTf) can catalyze the formation of enol silyl ethers, which is used to construct complex drug skeletons.
Cyanation reaction: TMSCN, as a mild reagent, participates in the cyanohydrin synthesis of aldehydes/ketones and is used for the preparation of chiral drug intermediates.
3. Drug molecule modification
Trifluoromethylation: TMSCF₃ is used as a nucleophile for trifluoromethyl modification of antiviral peptides or hormone regulators.
Silylation derivatization: Used for structural modification of anti-myelofibrosis drugs (such as ruxolitinib).
4. Other key applications
Dealkylation reaction: Trimethyl iodosilane can efficiently remove ether, acetal and other protecting groups, and is suitable for the synthesis of lactone drugs.
Free radical reduction: Trisilane (such as TTMSS) acts as a hydrogen donor to participate in carbonyl reduction or carbon-halogen bond cleavage
Production methodprocess of Trimethylsilyl powder
1. Direct synthesis method (industrial mainstream)
Reaction of silicon powder with methyl chloride: Under the catalysis of cuprous chloride, silicon powder and methyl chloride directly react to form a mixture of methylchlorosilanes (including trimethylchlorosilane), which is purified by fractionation to obtain the target product.
2. Laboratory preparation method
Tetramethylsilane conversion: In the presence of aluminum chloride, tetramethylsilane reacts with acetyl chloride to form trimethylchlorosilane.
Metal reagent method : For example, the synthesis of allyltrimethylsilane is obtained by reacting sodium powder or lithium metal with allyl chloride, and then quenching with trimethylchlorosilane (ClSiMe₃).
3. Derivatization production
Hexamethyldisiloxane conversion: Using hexamethyldisiloxane and phosphorus trichloride as raw materials, tris(trimethylsilyl)phosphite is prepared under the action of a catalyst, and the by-product can be recycled.
4. Other silanization reagents
Tris(trimethylsilyl)silane: prepared by a specific silanization reaction, used for functionalization of alkenes/alkynes
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