Substance
ID:717531
Names and Identifiers
IUPAC Traditional name
hexamethyldisilizane
IUPAC name
bis(trimethylsilyl)amine
Synonyms
HMDSHexamethyldisilazaneBis(trimethylsilyl)amine六甲基二硅杂氮烷
Registration numbers
CAS Number
MDL Number
Beilstein Number
Merck Index
EC Number
Properties
Safety Information
GHS Hazard statements
H225-H311-H331-H302-H314-H318
Safety Statements
16-26-33-36/37/39-45-60
Hazard Class
3
GHS Pictograms
Flammable gases, category 1
Flammable aerosols, categories 1,2
Flammable liquids, categories 1,2,3
Self-reactive substances and mixtures, Types B,C,D,E,F
Pyrophoric liquids, category 1
Pyrophoric solids, category 1
Self-heating substances and mixtures
Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3
Organic peroxides, Types B,C,D,E,F
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
Acute toxicity (oral, dermal, inhalation), categories 1,2,3
European Hazard Symbols
Harmful (X)
Flammable (F)
Corrosive (C)Risk Statements
11-20/21/22-34
UN Number
UN2924
TSCA Listed
是
GHS Precautionary statements
P210-P303+P361+P353-P305+P351+P338-P361-P405-P501A
RTECS
JM9230000
Storage Warning
Moisture Sensitive
Packing Group
II
Physical Property
Melting Point
-78°C
Density
0.774
Boiling Point
126°C
Refractive Index
1.4080
Flash Point
8°C(46°F)
Product Information
Purity
98+%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• 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).
• Convenient, mild silylating reagent which generates gaseous ammonia as the only by-product (see Appendix 4). Non-acidic substrates normally require a catalyst.
• 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).
• 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).
• In combination with DMSO, thiols are oxidized to disulfides under nearly neutral conditions: Synlett, 346 (2002).
• 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.
• 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.