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ChemicalBook--->CAS DataBase List--->15500-60-4

15500-60-4

15500-60-4 Structure

15500-60-4 Structure
IdentificationMore
[Name]

N,N-Bis(trimethylsilyl)formamide
[CAS]

15500-60-4
[Synonyms]

BIS-N N-(TRIMETHYLSILYL)FORMAMIDE
BSF
N,N-BIS(TRIMETHYLSILYL)FORMAMIDE
n,n-bis(trimethylsilyl)-formamid
N,N-Bis-(trimethylsilyl)-formamide(BSF)
BIS-N N-(TRIMETHYLSILYL)FORMAMIDE 97%
[EINECS(EC#)]

239-530-4
[Molecular Formula]

C7H19NOSi2
[MDL Number]

MFCD00014849
[Molecular Weight]

189.4
[MOL File]

15500-60-4.mol
Chemical PropertiesBack Directory
[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.
[pka]

0.16±0.70(Predicted)
[CAS DataBase Reference]

15500-60-4(CAS DataBase Reference)
[EPA Substance Registry System]

15500-60-4(EPA Substance)
Safety DataBack Directory
[Risk Statements ]

R10:Flammable.
[RIDADR ]

UN 1993 3/PG 3
[WGK Germany ]

3
[F ]

10-21
[HazardClass ]

3.2
[PackingGroup ]

III
Hazard InformationBack Directory
[Physical properties]

81–82 °C/20 mmHg; 154 °C/760 mmHg; mp 16–17 °C; n20 D 1.4388.
[Uses]

N,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.
[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.

15500-60-4 synthesis

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