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N,N-Bis(trimethylsilyl)formamide

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N,N-Bis(trimethylsilyl)formamide Basic information
Product Name:N,N-Bis(trimethylsilyl)formamide
Synonyms:n,n-bis(trimethylsilyl)-formamid;N,N-BIS(TRIMETHYLSILYL)FORMAMIDE;BSF;BIS-N N-(TRIMETHYLSILYL)FORMAMIDE;N,N-Bis-(trimethylsilyl)-formamide(BSF);BIS-N N-(TRIMETHYLSILYL)FORMAMIDE 97%;Formamide, N,N-bis(trimethylsilyl)-
CAS:15500-60-4
MF:C7H19NOSi2
MW:189.4
EINECS:239-530-4
Product Categories:
Mol File:15500-60-4.mol
N,N-Bis(trimethylsilyl)formamide Structure
N,N-Bis(trimethylsilyl)formamide Chemical Properties
Melting point 158 °C
Boiling point 158 °C
density 0.885 g/mL at 20 °C(lit.)
refractive index n20/D 1.437
Fp 37 °C
solubility benzene, CCl4, CH2Cl2, CHCl3.
pka0.16±0.70(Predicted)
CAS DataBase Reference15500-60-4(CAS DataBase Reference)
EPA Substance Registry SystemFormamide, N,N-bis(trimethylsilyl)- (15500-60-4)
Safety Information
Risk Statements 10
RIDADR UN 1993 3/PG 3
WGK Germany 3
10-21
HazardClass 3.2
PackingGroup III
MSDS Information
ProviderLanguage
SigmaAldrich English
N,N-Bis(trimethylsilyl)formamide Usage And Synthesis
Physical properties81–82 °C/20 mmHg; 154 °C/760 mmHg; mp 16–17 °C; n20 D 1.4388.
UsesN,N-Bis(trimethylsilyl)formamide can be used as source of nucleophilic formamide and N-silylaldimine synthon.
N,N-Bis(trimethylsilyl)formamide (BSF) exists in the amide form with both silyl groups attached to the nitrogen atom. This is in contrast to most other bis(TMS)amides (e.g., bis(TMS)- acetamide), which favor the N,O-bis(TMS)imidate isomer. BSF behaves as an N-formamido nucleophile, reacting with the carbonyl group of aldehydes and activated ketones to give N-formyl-O-trimethylsilyl-N,O-acetals. Similarly, reaction with imines (or their precursors) can in some cases give N-formylN,N-acetals. BSF undergoes reactions with a range of other electrophiles including acid chlorides, chloroformate esters, and isocyanates to give a range of interesting products. When treated with organolithium nucleophiles, attack occurs at the carbonyl function, to provide N-silylaldimines after elimination of a silyloxy unit. Such imines are reported to undergo further reactions to give heterocycles. There are also reports of BSF acting as a silylating agent, to give silyl enol ethers, although it is not commonly used for this application.
Preparationchlorotrimethylsilane 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.

15500-60-4 synthesis

N,N-Bis(trimethylsilyl)formamide Preparation Products And Raw materials
Preparation ProductsBenzeneacetaMide, N-forMyl-
Tag:N,N-Bis(trimethylsilyl)formamide(15500-60-4) Related Product Information
N-Methylformamide Formamide N,N-Dimethylformamide N-(Trimethylsilyl)acetamide BIS(TRIMETHYLSILYL) SULFATE 4-PREGNEN-18-AL-11BETA,21-DIOL-3,20-DIONE 18,21-DIACETATE 3-O-CARBOXYMETHYLOXIME:BSA N,N-Bis(trimethylsilyl)acetamide 11-ALPHA-HYDROXYTESTOSTERONE 11-HEMISUCCINATE : BSA N,N-Bis(trimethylsilyl)formamide