| Bis(trimethylsilyl)amine[1] | |
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| IUPAC name | 1,1,1,3,3,3-Hexamethyldisilazane |
| Other names | Bis(trimethylsilyl)amine Hexamethyldisilazane Hexamethyldisilane HMDS |
| Identifiers | |
| CAS number | |
| SMILES | CSi(C)(C)NSi(C)(C)C |
| Properties | |
| Molecular formula | C6H19NSi2 |
| Molar mass | 161.40 g/mol |
| Density | 0.76 g/cm3 |
| Melting point |
-78 °C |
| Boiling point |
125 °C |
| Hazards | |
| MSDS | External MSDS |
| NFPA 704 |
 3
1
1
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| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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 non-nucleophilic bases: Examples of these bases are:
- Lithium bis(trimethylsilyl)amide (LiHMDS)
- Sodium bis(trimethylsilyl)amide (NaHMDS)
- Potassium bis(trimethylsilyl)amide (KHMDS)
Contents |
Uses in organic chemistry
One of the uses of HMDS is as a reagent in condensation reactions of heterocyclic compounds such as in the microwave synthesis of a derivative of xanthine[2]:
Other uses
HMDS is often used in Photolithography as an adhesion promoter for Photoresist. Best results are obtained by applying HMDS from the gas phase on heated substrates.[3]
See also
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
- ^ http://www.photoresists.eu/photoresist_1412.html
