766917
Lithium bis(trimethylsilyl)amide solution
1.5 M in THF
Synonym(s):
Hexamethyldisilazane lithium salt
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About This Item
Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
Molecular Weight:
167.33
UNSPSC Code:
12352111
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3567910
Concentration:
1.5 M in THF
Form:
liquid
InChI key
YNESATAKKCNGOF-UHFFFAOYSA-N
SMILES string
[Li]N([Si](C)(C)C)[Si](C)(C)C
InChI
1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
form
liquid
concentration
1.5 M in THF
density
0.893 g/mL at 25 °C
Quality Level
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Application
Lithium bis(trimethylsilyl)amide can be used as a reagent:
- In the deprotonation and nucleophilic difluoromethylation reactions.
- 3-methoxy substituted dihydropyrrole derivatives by reacting with aldehydes and lithiated methoxyallene via in situ formations of N-trimethylsilylated imines.
- In Darzens condensation and directed aldol condensation reactions.
- To synthesize poly(N-octyl-p-benzamide)s by chain-growth polycondensation of 4-octylaminobenzoic acid methyl ester.
General description
Lithium bis(trimethylsilyl)amide is commonly used in organic synthesis as a non-nucleophilic strong Bronsted base. It is soluble in most nonpolar solvents such as aromatic hydrocarbons, hexanes, and THF.
signalword
Danger
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Self-heat. 1 - Skin Corr. 1B - STOT SE 3
target_organs
Central nervous system, Respiratory system
supp_hazards
Storage Class
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 2
flash_point_f
31.3 °F - closed cup
flash_point_c
-0.4 °C - closed cup
Regulatory Information
危险化学品
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Daniele Fabbri et al.
Environmental science & technology, 42(8), 2957-2963 (2008-05-24)
Using the pyrolysis-gas chromatography-mass spectrometry and off-line pyrolysis/silylation methods for lignites from three Miocene brown coal basins of Poland resulted in the characterization of many organic compounds, including dominant cellulose degradation products such as levoglucosan, 1,6-anhydro-beta-D-glucofuranose, and 1,4:3,6-dianhydroglucopyranose. Levoglucosan is
A Sebok et al.
Journal of chromatography. A, 1211(1-2), 104-112 (2008-10-14)
This paper presents a derivatization, mass fragmentation study relating to the most common six cholic acids, such as cholic, lithocholic, chenodeoxycholic, ursodeoxycholic, 3-hydroxy,7-ketocholanic and dehydrocholic acids, identified and quantified as pollutants in the aquatic environment at the first time. Derivatizations
Hexamethyldisilazane-mediated controlled polymerization of alpha-amino acid N-carboxyanhydrides.
Hua Lu et al.
Journal of the American Chemical Society, 129(46), 14114-14115 (2007-10-30)
Jerry Isaacson et al.
Angewandte Chemie (International ed. in English), 48(10), 1845-1848 (2009-01-29)
(-)-Dysibetaine has been synthesized in 11 steps from readily available L-malic acid (see scheme). The key step is a unique Ugi 4-center-3-component cyclization reaction, where an ester group acts as the carboxylic acid component. The use of 1,1,1,3,3,3-hexamethyldisilazane as an
Natalie M Clark et al.
Chemical communications (Cambridge, England), (39)(39), 5835-5837 (2009-09-30)
'Conventional' (-)-sparteine adducts of lithium and sodium 1,1,1,3,3,3-hexamethyldisilazide (HMDS) were prepared and characterised, along with an unexpected and 'unconventional' hydroxyl-incorporated sodium sodiate, [(-)-sparteine x Na(mu-HMDS)Na x (-)-sparteine](+)[Na(4)(mu-HMDS)(4)(OH)](-)--the complex anion of which is the first inverse crown ether anion.
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