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324671

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide

95%

Synonym(s):

Hexamethyldisilazane potassium salt, Potassium hexamethyldisilazide

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About This Item

Linear Formula:
[(CH3)3Si]2NK
CAS Number:
40949-94-8
Molecular Weight:
199.48
Beilstein:
4006754
MDL number:
MFCD00010330
UNSPSC Code:
12352111
PubChem Substance ID:
24859460
NACRES:
NA.22

Quality Level

200

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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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
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Organic metal compounds (except alkyl aluminum and alkyl lithium)
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

JAN Code

324671-BULK:
324671-VAR:
324671-100G:
324671-5G:
324671-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN8929
SHBP0945
SHBP0946
SHBN5029
SHBM8885

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Organometallics, 11, 2003-2003 (1992)
Organometallics, 12, 2618-2618 (1993)
The Journal of Organic Chemistry, 58, 6177-6177 (1993)
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
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)
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