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Sigma-Aldrich

Potassium bis(trimethylsilyl)amide

95%

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Synonym(s):
Hexamethyldisilazane potassium salt, Potassium hexamethyldisilazide
Linear Formula:
[(CH3)3Si]2NK
CAS Number:
Molecular Weight:
199.48
Beilstein:
4006754
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

95%

SMILES string

C[Si](C)(C)N([K])[Si](C)(C)C

InChI

1S/C6H18NSi2.K/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1

InChI key

IUBQJLUDMLPAGT-UHFFFAOYSA-N

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702722277304775061
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

General description

Potassium bis(trimethylsilyl)amide is commonly abbreviated as KHMDS with molecular formula [(CH3)3Si]2NK. It is widely used as Bronsted base in synthesis.

KHMDS is a base catalyst, that shows high activity and selectivity for the alkylation of alkylpyridines.

Application

Anionic initiator used in the preparation of poly(ethylene oxide). Sterically hindered base employed in selective cyclization reactions. Also used in the preparation of lanthanide complexes.

Features and Benefits

Potassium bis(trimethylsilyl)amide (KHMDS):
  • Easily available.
  • Good selectivity for the benzylic C−H bonds.
  • Good reactivity for sterically crowded C−H bonds.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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The Journal of Organic Chemistry, 58, 6177-6177 (1993)
Synthesis of poly(ethylene oxide) with heterobifunctional reactive groups at its terminals by an anionic initiator.
M Yokoyama et al.
Bioconjugate chemistry, 3(4), 275-276 (1992-07-01)
Aeilke J Kamphuis et al.
ChemSusChem, 12(15), 3635-3641 (2019-05-01)
The development of new families of active and selective single-component catalysts based on earth-abundant metal is of interest from a sustainable chemistry perspective. In this context, anionic mono(formazanate) iron(II) complexes bearing labile halide ligands, which possess both Lewis acidic and
Organometallics, 12, 2618-2618 (1993)
Organometallics, 11, 2003-2003 (1992)

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