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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

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About This Item

Linear Formula:
[(CH3)3Si]2NNa
CAS Number:
1070-89-9
Molecular Weight:
183.37
Beilstein:
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

Signal Word

Danger

Hazard Statements

H225,H314,H335,H336,H351

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH014,EUH019

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Sodium Hexamethyldisilazide.
Watson B T and Lebel H
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2005)
(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)
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