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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 Chemical Properties |
| Risk Statements | 10 | | RIDADR | UN 1993 3/PG 3 | | WGK Germany | 3 | | F | 10-21 | | HazardClass | 3.2 | | PackingGroup | III |
| | N,N-Bis(trimethylsilyl)formamide Usage And Synthesis |
| 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. 
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| | N,N-Bis(trimethylsilyl)formamide Preparation Products And Raw materials |
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