225770
Lithium bis(trimethylsilyl)amide solution
1.0 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:
1.0 M in THF
Form:
liquid
form
liquid
Quality Level
concentration
1.0 M in THF
density
0.891 g/mL at 25 °C
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
InChI key
YNESATAKKCNGOF-UHFFFAOYSA-N
General description
Lithium bis(trimethylsilyl)amide (LHMDS) is a non-nucleophilic strong base widely used in organic synthesis for deprotonation reactions and base-catalyzed reactions. It is generally soluble in most nonpolar organic solvents.
Application
Lithium bis(trimethylsilyl)amide solution (1.0 M in THF) can be used as a base:
- To catalyze polymerization reaction in the synthesis of poly(p-benzamide)s.
- In the synthesis of cyclic poly(α-peptoid)s and α-(difluoromethyl)styrene.
- In directed aldol condensations and Darzens condensation reactions; α-arylation of aryl ester derivatives and allylic amination reaction.
- For the generation of kinetic enolates than sodium hexamethyldisilazide (NaHMDS) because the enolates produced are more regiostable than those produced with NaHMDS.
Packaging
The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
Legal Information
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC
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Danger
hcodes
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
target_organs
Central nervous system, Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
flash_point_f
1.4 °F - closed cup
flash_point_c
-17 °C - closed cup
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? -(Difluoromethyl) styrene: improved approach to grams scale synthesis
Justyna WK,et al.
Journal of Fluorine Chemistry, 179, 175-178 (2015)
Macromolecules, 39, 5347-5347 (2006)
Elsa Vennat et al.
Dental materials : official publication of the Academy of Dental Materials, 25(6), 729-735 (2009-01-29)
The objectives of this study were to assess demineralized dentin porosity and quantify the different porous features distribution within the material using mercury intrusion porosimetry (MIP) technique. We compared hexamethyldisilazane (HMDS) drying and lyophilization (LYO) (freeze-drying) in sample preparation. Fifty-six