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Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution

40% in THF

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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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This Item
245585702722277304
concentration

40% in THF

concentration

1.0 M in THF

concentration

1 M in THF

concentration

0.5 M in toluene

Application

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

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

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Customers Also Viewed

Slide 1 of 7

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Silylated Amines II. A New, Highly Variable Amine Synthesis by the N,N-Bis(trimethylsilyl)aminomethylation of Grignard Compounds.
Bestmann H J, et al.
Synthesis, 1987(09), 848-850 (1987)
Regio and stereoselective preparation of enolates from ketones by means of sodium bis (trimethylsilyl)-azide.
Gaudemar M and Bellassoued M
Tetrahedron Letters, 30(21), 2779-2782 (1989)
Eine einfache Synthese primarer Amine uber ihre N, N?Bis (trimethylsilyl)?Derivate.
Bestmann H J and Wolfel G
Chemische Berichte, 117(3), 1250-1254 (1984)
(E)?Selective Wittig Reactions between a Nonstabilized Phosphonium Ylide Bearing a Phosphastibatriptycene Skeleton and Benzaldehydes.
Uchiyama Y, et al.
European Journal of Organic Chemistry, 2017(1), 159-174 (2017)
Sodium Hexamethyldisilazide.
Watson B T and Lebel H
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2005)

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