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Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution

40% in THF

Synonym(s):

HMN-Na Sol, NaHMDS solution, Hexamethyldisilazane sodium salt solution

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About This Item

Linear Formula:
[(CH3)3Si]2NNa
CAS Number:
1070-89-9
Molecular Weight:
183.37
Beilstein/REAXYS Number:
3629917
MDL number:
MFCD00009835
UNSPSC Code:
12352111
PubChem Substance ID:
57652836
NACRES:
NA.22

form

liquid

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. 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

signalword

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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)
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)
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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