577928
Lithium bis(trimethylsilyl)amide solution
1 M in toluene
Synonym(s):
LiHMDS, 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 M in toluene
Quality Level
concentration
1 M in toluene
density
0.860 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 solution (LiHMDS) is generally used in organic synthesis as a non-nucleophilic strong Bronsted base.
Application
LiHMDS can be used as a reagent:
- In the deprotonation and nucleophilic difluoromethylation reactions.
- To synthesize isoquinoline derivatives by the addition of N-iodosuccinimide (NIS) to the α-benzyl tosylmethyl isocyanides.
- To prepare arylboronic acid pinacol esters by the reaction of aryl fluorides with bis(pinacolato)diboron via palladium-catalyzed cross-coupling reaction.
Lithium bis(trimethylsilyl)amide is generally used in organic synthesis as a non-nucleophilic strong Brønsted base. It can be used for salt metathesis reaction for the synthesis of cesium bis(trimethylsilyl)amide (CsHMDS) and lithium fluoride by reacting with cesium fluoride.
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signalword
Danger
Hazard Classifications
Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Self-heat. 1 - Skin Corr. 1B - STOT RE 2 - STOT SE 3
target_organs
Central nervous system
supp_hazards
Storage Class
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 3
flash_point_f
48.0 °F - closed cup
flash_point_c
8.9 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Regulatory Information
易制毒化学品（3类）
危险化学品
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Structural Studies of Cesium, Lithium/Cesium, and Sodium/Cesium Bis (trimethylsilyl) amide (HMDS) Complexes
Ojeda-Amador AI, et al.
Inorganic Chemistry, 55(11), 5719-5728 (2016)
Lithium and potassium bis (trimethylsilyl) amide: Utilizing non-nucleophilic bases as nitrogen sources
Bruning J, et al.
Tetrahedron Letters, 38(18), 3187-3188 (1997)
Tatsuya Nitabaru et al.
Journal of the American Chemical Society, 131(38), 13860-13869 (2009-09-10)
Full details of an anti-selective catalytic asymmetric nitroaldol reaction promoted by a heterobimetallic catalyst comprised of Nd(5)O(O(i)Pr)(13), an amide-based ligand, and NaHMDS (sodium hexamethyldisilazide) are described. A systematic synthesis and evaluation of amide-based ligands led to the identification of optimum
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 577928-100ML | 04061837674150 |
| 577928-800ML | 04061837674167 |