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
Beilstein/REAXYS Number:
3567910
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22
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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
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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
wgk_germany
WGK 2
flash_point_f
1.4 °F - closed cup
flash_point_c
-17 °C - closed cup
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