15500-60-4

Usage

Uses

Used in Organic Synthesis:
N,N-Bis(trimethylsilyl)formamide is used as a source of nucleophilic formamide and N-silylaldimine synthon for various organic synthesis applications. It reacts with the carbonyl group of aldehydes and activated ketones to give N-formyl-O-trimethylsilyl-N,O-acetals. Additionally, it can react with imines (or their precursors) to produce N-formylN,N-acetals in some cases.
Used in the Formation of Heterocycles:
When treated with organolithium nucleophiles, BSF undergoes attack at the carbonyl function, leading to the formation of N-silylaldimines after the elimination of a silyloxy unit. These imines are known to undergo further reactions to give heterocycles, which are important in the synthesis of complex organic molecules.
Used in the Synthesis of Silyl Enol Ethers:
Although not commonly used for this application, BSF has been reported to act as a silylating agent, which can be used to produce silyl enol ethers. These compounds are valuable intermediates in organic synthesis, particularly in the formation of carbon-carbon bonds.
Physical Properties:
N,N-Bis(trimethylsilyl)formamide has a melting point of 16-17 °C and exhibits different boiling points under varying pressure conditions, such as 81-82 °C at 20 mmHg and 154 °C at 760 mmHg. Its refractive index is n20 D 1.4388, which is an important parameter for characterizing its optical properties.

Preparation

chlorotrimethylsilane was added at room temperature to a solution of formamide and triethylamine in dry benzene and the mixture was heated at reflux for 1 h. The reaction mixture was filtered, and the filtrate was evaporated to give a crude oil. This was purified by high-vacuum distillation to afford N,N-bis(trimethylsilyl)formamide (BSF) as an oil in 75% yield.

InChI:InChI=1/C7H19NOSi2/c1-10(2,3)8(7-9)11(4,5)6/h7H,1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 77287-34-4 formamide 
• 124-38-9 carbon dioxide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 4252-31-7 N-formylbenzamide 
• 30690-19-8 N-Formylcarbamidsaeure-methylester 
• 59025-32-0 5-aminomethylenebarbituric acid 
• 146953-87-9 5-benzyl-4-butylimidazole 
• 2198-45-0 5-aminononane 
• 623-93-8 5-nonanol 
• 125606-87-3 (3S,4R)-4-sec-Butyl-3-isopropyl-azetidin-2-one 
• 32083-31-1 (E)-3-Amino-2-(4-chloro-benzenesulfonyl)-acrylonitrile 
• 65649-93-6 2,2-Bis-(toluene-4-sulfonyl)-vinylamine 
• 2871-11-6 Toluene-4-sulfonate1-methyl-2-{(E)-3-[1-methyl-1H-quinolin-(2Z)-ylidene]-propenyl}-quinolinium; 
• 822-36-6 4-methyl-1H-imidazole 
• 86061-91-8 benzyl 6α-formamido-6β-<(2,2,2-trichloroethoxy)carbonylamino>penicillanate 
• 131788-83-5 (6R,7S)-7-Amino-3-chloromethyl-7-formylamino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 136981-80-1 (6R,7R)-3-Acetoxymethyl-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-formylamino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of 1-acylamino-1-(trimethylsiloxy)alkanes by trimethylsilyl trifluoromethanesulfonate-catalysed addition of bis(trimethylsilyl)amides to aldehydes

Bis(trimethylsilyl)formamide reacts with aldehydes in refluxing chloroform, or at room temperature with catalysis by trimethylsilyl trifluoromethanesulfonate, to give 1-acylamino-1-(trimethylsiloxy)alkanes; similar results are obtained with other bis(trimethylsilyl)amides, but surprisingly not with bis(trimethylsilyl)acetamide, and addition of bis(trimethylsilyl)formamide to ketones and acetals can also be accomplished using TMS triflate as catalyst.

A NHC-silyliumylidene cation for catalytic N?formylation of amines using carbon dioxide

This study describes the use of a silicon(II) complex, namely, the NHC-silyliumylidene cation complex [(IMe)2SiH]I (1, IMe =:C{N(Me)C(Me)}2), to catalyze the chemoselective N-formylation of primary and secondary amines using CO2 and PhSiH3 under mild conditions to afford the corresponding formamides as a sole product (average reaction time: 4.5 h; primary amines, average yield: 95%, average TOF: 8 h?1; secondary amines, average yield: 98%, average TOF: 17 h?1). The activity of 1 and product yields outperform the currently available non-transition-metal catalysts used for this catalysis. Mechanistic studies show that the silicon(II) center in complex 1 catalyzes the C?N bond formation via a different pathway in comparison with non-transition-metal catalysts. It sequentially activates CO2, PhSiH3, and amines, which proceeds via a dihydrogen elimination mechanism, to form formamides, siloxanes, and dihydrogen gas.

Method for the preparation of persilylated carboxylic acid amides

Disclosed is a method of preparing bis-trimethylsilylamides of carboxylic acids from the carboxylic acid amide by mixing two equivalents of trimethylchlorosilane and an excess of hexamethyldisilazane, heating the mixture to 40° to 80° C. and adding two equivalents of a tertiary amine as acid acceptor. The method results in substantially improved purity and yield of end product.