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80631

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution

40% in THF

Synonym(s):
HMN-Na Sol, NaHMDS solution, Hexamethyldisilazane sodium salt solution
Linear Formula:
[(CH3)3Si]2NNa
CAS Number:
Molecular Weight:
183.37
Beilstein:
3629917
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

concentration

40% in THF

SMILES string

C[Si](C)(C)N([Na])[Si](C)(C)C

InChI

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

InChI key

WRIKHQLVHPKCJU-UHFFFAOYSA-N

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Application

  • Sodium bis(trimethylsilyl)amide, also known as NaHMDS, is a metal dialkylamide reagent that combines both high basicity and nucleophilicity.
[64] It is a general reagent used for the enolization of carbonyl compounds.[65]
  • It can be used to prepare phosphonium ylides in Wittig reaction.
  • [66]
  • NaHMDS solution can also be used as a source of nitrogen in aminomethylation
  • [67] and in the synthesis of primary amines from the corresponding alkyl halides.[68]

    Packaging

    500 mL in Sure/Seal™

    Other Notes

    prices for bulk quantities on request

    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

    Personal Protective Equipment

    dust mask type N95 (US), Eyeshields, Gloves

    Certificate of Analysis

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    Certificate of Origin

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