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

A15139 Hexamethyldisilazane, 98+%

Codice CAS
999-97-3
Sinonimi
Bis(trimethylsilyl)amine
HMDS

Dimensioni Prezzo ($) Quantità Disponibilità
25ml 17,20
100ml 26,50
500ml 63,40
2500ml 255,00
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Hexamethyldisilazane, 98+%

MDL
MFCD00008259
EINECS
213-668-5

Proprietà chimiche

Formula
C6H19NSi2
Peso formula
161.40
Punto di fusione
-78°
Punto di ebollizione
126°
Punto di infiammabilità
8°(46°F)
Densità
0.774
Indice di rifrazione
1.4080
Sensibilità
Moisture Sensitive
Solubilità
Miscible with methanol, chloroform, ethyl ether and benzene. Immiscible with water.                    

Applicazioni

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.

Note

Incompatible with strong oxidizing agents and strong acids.  

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H225-H302-H311-H331-H314-H318

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

Dichiarazioni precauzionali: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Merck
14,4689
Beilstein
635752
Classe di rischio
3
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.90
TSCA
Yes
RTECS
JM9230000

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