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Sigma-Aldrich

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
Beilstein/REAXYS Number:
3567910
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22

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

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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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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

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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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)
Synthesis of 1-Substituted Isoquinolines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Cassiarin A
Gutierrez S, et al.
Organic Letters, 38(18), 187-208 (2016)
LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides
Zhao X, et al.
Organic Letters, 38(18), 25-44 (2011)
Selective fluoroalkylation of organic compounds by tackling the ?negative fluorine effect?
Fluorous chemistry, 38(18), 187-208 (2016)
Development of synthetic routes to dolutegravir
Syntheses of Heterocyclic Compounds Synthesis of Heterocycles in Contemporary Medicinal Chemistry, 38(18), 3187-3188 (1997)

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