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Bis(trimethylsilyl)amine



Bis(trimethylsilyl)amine[1]
IUPAC name 1,1,1,3,3,3-Hexamethyldisilazane
Other names Bis(trimethylsilyl)amine
Hexamethyldisilazane
Hexamethyldisilane
HMDS
Identifiers
CAS number 999-97-3
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
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox 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 non-nucleophilic bases:

Examples of these bases are:

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

  1. ^ Merck Index, 13th Edition, 4708.
  2. ^ 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
  3. ^ http://www.photoresists.eu/photoresist_1412.html
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Bis(trimethylsilyl)amine". A list of authors is available in Wikipedia.
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