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
Regulatory Information
危险化学品
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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)
Nur Hazlin Hazrin-Chong et al.
Journal of microbiological methods, 90(2), 96-99 (2012-05-09)
The use of hexamethyldisilazane (HMDS) as a drying agent was investigated in the specimen preparation for scanning electron microscopy (SEM) imaging of bacterial surface colonization on sub-bituminous coal. The ability of microbes to biofragment, ferment and generate methane from coal
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 225770-100L | 04061837670596 |
| 225770-2X2ML | 04061837670138 |
| 225770-4X100ML | 04061838779731 |
| 225770-800ML | 04061838779755 |
| 225770-100ML | 04061838779717 |
| 225770-1L | 04061838779724 |
| 225770-18L-KL | 04061837670602 |
| 225770-8L | 04061838779762 |
| 225770-PZ | 04061823820189 |
| 225770-4X25ML | 04061838779748 |