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999-97-3 - Hexamethyldisilazane, 98+% - Bis(trimethylsilyl)amine - HMDS - A15139 - Alfa Aesar

A15139 Hexamethyldisilazane, 98+%

CAS Number
999-97-3
Synonyms
Bis(trimethylsilyl)amine
HMDS

Size Price ($) Quantity Availability
25ml 17.10
100ml 26.37
500ml 63.68
2500ml 253.38
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Hexamethyldisilazane, 98+%

MDL
MFCD00008259
EINECS
213-668-5

Chemical Properties

Formula
C6H19NSi2
Formula Weight
161.40
Melting point
-78°
Boiling Point
126°
Flash Point
8°(46°F)
Density
0.774
Refractive Index
1.4080
Sensitivity
Moisture Sensitive
Solubility
Miscible with methanol, chloroform, ethyl ether and benzene. Immiscible with water.                    

Applications

Hexamethyldisilazane is used as a solvent in organic synthesis and organometallic chemistry. It is often used as an adhesion promoter for photoresist in photolithography. Further, it is used for the preparation of trimethylsilyl ethers from hydroxy compounds. It is used as an alternative to critical point drying during sample preparation in electron microscopy. It is added to analyte to get silylated diagnostic products during pyrolysis in gas chromatography- mass spectrometry.

Notes

Incompatible with strong oxidizing agents and strong acids.  

Literature References

Convenient, mild silylating reagent which generates gaseous ammonia as the only by-product (see Appendix 4). Non-acidic substrates normally require a catalyst.

Silylation of alcohols, including carbohydrates, is catalyzed by TMS chloride: J. Org. Chem., 23, 50 (1958); J. Am. Chem. Soc., 85, 2497 (1963); Chem. Ind. (London), 794 (1984). Silylation of phenols occurs readily, see also: Liebigs Ann. Chem., 20 (1973).

HMDS in the presence of TMS chloride permits the selective O-silylation of amino alcohols: Synthesis, 990 (1988). Alcohols and phenols can be silylated in the presence of amines and thiols with ZnCl2 as catalyst: Synth. Commun., 23, 1633 (1993).

For conversion of carbonyl groups to silyl enol ethers, see Iodotrimethyl­silane, A12902.

A range of catalysts for silylation with HMDS, including saccharin and sodium saccharin, has been recommended: J. Org. Chem., 47, 3966 (1982), for silylation of alcohols, phenols, thiols, carboxylic acids, amides, thioamides, hydroxamic acids, hydrazides, NH-groups of heterocycles, hydrazines, 1,3-diketones, etc. The use of TBAF (0.02 eq.) or iodine (0.01 eq.) also provide mild procedures for O-silylation: Tetrahedron Lett., 35, 8409 (1994); J. Org. Chem., 65, 7228 (2000).

Can also function as a protected form of ammonia, e.g. to convert acid chlorides to primary amides: Synthesis, 517 (1985), and substituted maleic anhydrides to maleimides: Tetrahedron Lett., 31, 5201 (1990).

In combination with DMSO, thiols are oxidized to disulfides under nearly neutral conditions: Synlett, 346 (2002).

The Na, Li and K derivatives are useful strong bases; see Sodium bis(trimethyl­silyl)­amide, L13352, Lithium bis(trimethyl­silyl)­amide, L15012, and Potassium bis(trimethyl­silyl)­amide, L15022.

Rumyantsev, Y. M.; Chagin, M. N.; Kosinova, M. L.; Kuznetsov, F. A. Synthesis of thin silicon carbonitride films from hexamethyldisilazane in an inductively coupled plasma reactor. Inorg. Mater. 2015, 51 (9), 897-902.

Chinga-Carrasco, G.; Kuznetsova, N.; Garaeva, M.; Leirset, I.; Galiullina, G.; Kostochko, A.; Syverud, K. Bleached and unbleached MFC nanobarriers: properties and hydrophobisation with hexamethyldisilazane. J. Nanopart. Res. 2012, 14 (12), 1-10.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H311-H331-H302-H314-H318

Highly flammable liquid and vapour. Toxic in contact with skin. Toxic if inhaled. Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P260-P261-P280-P303+P361+P353-P305+P351+P338-P361-P301+P330+P331-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,4689
Beilstein
635752
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
JM9230000

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