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Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution

1.0 M in THF

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Synonym(s):
Hexamethyldisilazane lithium salt
Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
Molecular Weight:
167.33
Beilstein:
3567910
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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

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This Item
577928324620920398
concentration

1.0 M in THF

concentration

1 M in toluene

concentration

-

concentration

-

density

0.891 g/mL at 25 °C

density

0.860 g/mL at 25 °C

density

0.860 g/mL at 25 °C (lit.)

density

0.860 g/mL at 25 °C (lit.)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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

Signal Word

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup


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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)
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
Hexamethyldisilazane-mediated controlled polymerization of alpha-amino acid N-carboxyanhydrides.
Hua Lu et al.
Journal of the American Chemical Society, 129(46), 14114-14115 (2007-10-30)

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