Bis(trimethylsilyl)amine
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| Bis(trimethylsilyl)amine[1] | |
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| Chemical name | 1,1,1,3,3,3-Hexamethyldisilazane |
| Other names | Bis(trimethylsilyl)amine Hexamethyldisilazane Hexamethyldisilane HMDS |
| Chemical formula | C6H19NSi2 |
| Molecular mass | 161.40 g/mol |
| CAS number | [999-97-3] |
| Density | 0.76 g/cm3 |
| Melting point | -78 °C |
| Boiling point | 125 °C |
| SMILES | CSi(C)(C)NSi(C)(C)C |
| NFPA 704 |
3
1
1
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| Disclaimer and references | |
Bis(trimethylsilyl)amine (also known as hexamethyldisilazane, or HMDS) a chemical reagent with molecular formula (CH3)3Si-NH-Si(CH3)3 which consists of ammonia substituted with two trimethylsilyl functional groups. It is a clear, colorless liquid that will hydrolize slowly upon exposure to water.
A bis(trimethylsilyl)amide (also known as hexamethyldisilazide) results from the deprotonation of the nitrogen atom of bis(trimethylsilyl)amines and are used as strong hindered bases:
Examples of these bases are:
- Lithium bis(trimethylsilyl)amide (LiHMDS)
- Sodium bis(trimethylsilyl)amide (NaHMDS)
- Potassium bis(trimethylsilyl)amide (KHMDS)
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[edit] Uses in organic chemistry
One of the uses of HMDS is as a catalyst in condensation reactions of heterocyclic compounds such as in the microwave synthesis of a derivative of xanthine [2]:
[edit] See also
[edit] References
- ^ Merck Index, 13th Edition, 4708.
- ^ Microwave-assisted Ring Closure Reactions: Synthesis of 8-substituted Xanthine Derivatives and related Pyrimido- and Diazepinopurinediones Burbiel J, Hockemeyer J, Mueller C Beilstein Journal of Organic Chemistry, 2006 2:20 ( 27 October 2006 ) DOI:10.1186/1860-5397-2-20
