N,N-Bis(trimethylsilyl)formamide
- CAS No.
- 15500-60-4
- Chemical Name:
- N,N-Bis(trimethylsilyl)formamide
- Synonyms
- 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
- Molecular Formula:
- C7H19NOSi2
- Molecular Weight:
- 189.4
- MOL File:
- 15500-60-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/5/4 15:13:22
| Melting point | 158 °C |
|---|---|
| Boiling point | 158 °C |
| Density | 0.885 g/mL at 20 °C(lit.) |
| refractive index |
n |
| Flash point | 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 | Formamide, N,N-bis(trimethylsilyl)- (15500-60-4) |
N,N-Bis(trimethylsilyl)formamide Chemical Properties,Uses,Production
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.
N,N-Bis(trimethylsilyl)formamide Preparation Products And Raw materials
N,N-Bis(trimethylsilyl)formamide Suppliers
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