577928

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution

1 M in toluene

Synonym(s):
LiHMDS, Hexamethyldisilazane lithium salt
Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
Molecular Weight:
167.33
Beilstein/REAXYS Number:
3567910
MDL number:
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.

Packaging

100, 800 mL in Sure/Seal™

Signal Word

Danger

hazcat

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_code

4.2 - Pyrophoric and self-heating hazardous materials

WGK Germany

WGK 2

Flash Point(F)

48.0 °F - closed cup

Flash Point(C)

8.9 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Lithium and potassium bis (trimethylsilyl) amide: Utilizing non-nucleophilic bases as nitrogen sources
Bruning J, et al.
Tetrahedron Letters, 38(18), 3187-3188 (1997)
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)
Jerry Isaacson et al.
Angewandte Chemie (International ed. in English), 48(10), 1845-1848 (2009-01-29)
(-)-Dysibetaine has been synthesized in 11 steps from readily available L-malic acid (see scheme). The key step is a unique Ugi 4-center-3-component cyclization reaction, where an ester group acts as the carboxylic acid component. The use of 1,1,1,3,3,3-hexamethyldisilazane as an...
Marko Marinkovic et al.
Advanced materials (Deerfield Beach, Fla.), 24(29), 4005-4009 (2012-06-26)
A model is presented that describes the gate-voltage-dependent contact resistance and channel-length-dependent charge carrier mobility of small-molecule-based organic thin-film transistors in top and bottom drain/source contact configuration.
Adrienne C Greene et al.
Biomaterials, 32(34), 8860-8869 (2011-09-03)
Chemical and topographical cues can be used to guide dissociated neurons into user-defined network geometries on artificial substrates, yet control of neuron polarity (differentiation into axons and dendrites) remains an elusive goal. We developed a dual guidance cue strategy for...

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