1011-57-0

Basic information

• Product Name: N-Trimethylsilylbenzamide
• Synonyms: N-Trimethylsilylbenzamide
• CAS NO: 1011-57-0
• Molecular Formula: C₁₀H₁₅NOSi
• Molecular Weight: 193.32
• Mol File: 1011-57-0.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Trimethylsilylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Trimethylsilylbenzamide(1011-57-0)
• EPA Substance Registry System: N-Trimethylsilylbenzamide(1011-57-0)

Safety Data

• Hazardous Substances Data: 1011-57-0(Hazardous Substances Data)

Usage

General Description

N-Trimethylsilylbenzamide is an organic compound with the chemical formula C11H15NO. It is a derivative of benzamide, a compound consisting of a benzene ring attached to a carbonyl group. N-Trimethylsilylbenzamide contains an additional trimethylsilyl group attached to the nitrogen atom of the amide functional group. N-Trimethylsilylbenzamide is commonly used as a reagent in organic synthesis, particularly in the protection of amine and phenol groups. N-Trimethylsilylbenzamide is also known for its ability to stabilize and protect sensitive functional groups during various chemical reactions. Overall, this compound plays a crucial role in the development of pharmaceuticals and other organic compounds.

Upstream product

• 4648-54-8 trimethylsilylazide 
• 100-52-7 benzaldehyde 
• 84635-79-0 2-amino-4,5-benzo-1,3,2-dioxaphospholane 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 75-77-4 chloro-trimethyl-silane 
• 55-21-0 benzamide 

Downstream Products

• 100-46-9 benzylamine 
• 14429-02-8 benzyl-(4-methoxybenzyl)amine 
• 46995-63-5 N-benzyl-1-(naphthalen-2-yl)methanamine 
• 55096-89-4 N-benzyl-1-(4-bromophenyl)methanamine 
• 13541-00-9 N-(4-chlorobenzyl)benzylamine 
• 7465-87-4 N-benzyl-4-methoxybenzamide 
• 149358-58-7 N-benzylnaphthalene-2-carboxamide 
• 80311-89-3 4-bromo-N-benzylbenzamide 
• 7461-34-9 N-benzyl-p-chlorobenzamide 
• 138768-32-8 N-((4-methoxyphenyl)(phenyl)methyl)benzamide 
• 4461-33-0 benzoyl isocyanate 
• 51933-60-9 N,N'-Thiobenzamidanilin 
• 51933-59-6 ethyl 2,2-bis(benzamido)acetate 
• 51933-56-3 N-Benzoyl-α-chlor-α-carboethoxymethansulfenamid 

Relevant articles and documents

Synthesis, structures and stereodynamic behavior of novel pentacoordinate (O→Si)-Chelate Difluoro(methyl)silylmethyl derivatives of amides and imides

The structures and stereodynamic behavior of (O→Si)-chelate methyldifluorosilanes in solutions were studied by multinuclear (1H, 13C, 19F, 29Si) and 2D (COSY, HETCOR 1H, 13C) NMR spectrosco

Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes

C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.

Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters

A novel efficient method was proposed for the synthesis of enantiopure precursors of taxane-containing cytostatics, i.e., methyl esters of (2R,3S)- and (2S,3R)-N-benzoylphenylisoserine and similar taxoid esters. The method is based on the regio- and stereoselective hydrobromolysis of the corresponding trans-β-phenyl glycidate enatiomers, consecutive reactions of O-acylcarbamoylation of the obtained 3-bromohydrins, intramolecular cyclization to 4-phenyloxazolidin-2-one-5-carboxylic acid derivatives, and oxazolidinone ring opening.