15500-60-4 Usage
Description
N,N-Bis(trimethylsilyl)formamide, also known as BSF, is a unique amide compound with both silyl groups attached to the nitrogen atom. It is characterized by its ability to act as an N-formamido nucleophile, which allows it to participate in various chemical reactions with different electrophiles. BSF is known for its distinct reactivity and potential applications in organic synthesis.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 15500-60-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,5,0 and 0 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 15500-60:
(7*1)+(6*5)+(5*5)+(4*0)+(3*0)+(2*6)+(1*0)=74
74 % 10 = 4
So 15500-60-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H19NOSi2/c1-10(2,3)8(7-9)11(4,5)6/h7H,1-6H3
15500-60-4Relevant articles and documents
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Yoder,C.H. et al.
, p. 4283 - 4286 (1974)
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A NHC-silyliumylidene cation for catalytic N?formylation of amines using carbon dioxide
Leong, Bi-Xiang,Teo, Yeow-Chuan,Condamines, Cloe,Yang, Ming-Chung,Su, Ming-Der,So, Cheuk-Wai
, p. 14824 - 14833 (2020/12/21)
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.
