Skip to Content
MilliporeSigma
All Photos(1)

Documents

577928

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution

1 M in toluene

Synonym(s):

LiHMDS, Hexamethyldisilazane lithium salt

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
4039-32-1
Molecular Weight:
167.33
Beilstein/REAXYS Number:
3567910
MDL number:
MFCD00008261
UNSPSC Code:
12352111
PubChem Substance ID:
24880899
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

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.

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

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Selective fluoroalkylation of organic compounds by tackling the ?negative fluorine effect?
Fluorous chemistry, 38(18), 187-208 (2016)
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)
Development of synthetic routes to dolutegravir
Syntheses of Heterocyclic Compounds Synthesis of Heterocycles in Contemporary Medicinal Chemistry, 38(18), 3187-3188 (1997)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service