Bis(trimethylsilyl)amine
From Wikipedia, the free encyclopedia
| 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 | [999-97-3] |
| SMILES | C[Si](C)(C)N[Si](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) is a chemical reagent with the 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.
Bis(trimethylsilyl)amide results from the deprotonation of the nitrogen atom of bis(trimethylsilyl)amines and are used as non-nucleophilic bases, including:
- Lithium bis(trimethylsilyl)amide (LiHMDS)
- Sodium bis(trimethylsilyl)amide (NaHMDS)
- Potassium bis(trimethylsilyl)amide (KHMDS)
Contents |
[edit] 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]
[edit] Other
In photolithography, HMDS is often used in as an adhesion promoter for photoresist. Best results are obtained by applying HMDS from the gas phase on heated substrates.[3]
In electron microscopy, HMDS can be used as an alternative to critical point drying during sample preparation.[4]
[edit] See also
[edit] References
- ^ Merck Index, 13th Edition, 4708.
- ^ Burbiel JC, Hockemeyer J, Müller CE (2006). "Microwave-assisted ring closure reactions: synthesis of 8-substituted xanthine derivatives and related pyrimido- and diazepinopurinediones". Beilstein J Org Chem 2: 20. doi:. PMID 17067400.
- ^ Cornell NanoScale Science & Technology Facility. CNF - Photolithography Resist Processes and Capabilities. Retrieved on 2008-01-29.
- ^ Bray DF, Bagu J, Koegler P (1993). "Comparison of hexamethyldisilazane (HMDS), Peldri II, and critical-point drying methods for scanning electron microscopy of biological specimens". Microsc. Res. Tech. 26 (6): 489–95. doi:. PMID 8305726.
