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N,N-??(??????)?????

N,N-??(??????)?????
N,N-??(??????)????? ??? ???
?? ??:
15500-60-4
???:
N,N-??(??????)?????
???(??):
N,N-??(??????)?????
???:
N,N-Bis(trimethylsilyl)formamide
???(??):
BSF;N,N-BIS(TRIMETHYLSILYL)FORMAMIDE;n,n-bis(trimethylsilyl)-formamid;BIS-N N-(TRIMETHYLSILYL)FORMAMIDE;Formamide, N,N-bis(trimethylsilyl)-;BIS-N N-(TRIMETHYLSILYL)FORMAMIDE 97%;N,N-Bis-(trimethylsilyl)-formamide(BSF)
CBNumber:
CB8480743
???:
C7H19NOSi2
??? ??:
189.4
MOL ??:
15500-60-4.mol

N,N-??(??????)????? ??

???
158 °C
?? ?
158 °C
??
0.885 g/mL at 20 °C(lit.)
???
n20/D 1.437
???
37 °C
???
??, CCl4, CH2Cl2, CHCl3? ???
?? ?? (pKa)
0.16±0.70(Predicted)
CAS ??????
15500-60-4(CAS DataBase Reference)
EPA
Formamide, N,N-bis(trimethylsilyl)- (15500-60-4)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
?? ???? ?? 10
????(UN No.) UN 1993 3/PG 3
WGK ?? 3
F ?????? 10-21
?? ?? 3.2
???? III
????(GHS): GHS hazard pictograms
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H226 ??? ?? ? ?? ??? ?? ?? 3 ??
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N,N-??(??????)????? C??? ??, ??, ??

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

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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.

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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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