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80631

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
UNSPSC Code:
12352111
NACRES:
NA.22
PubChem Substance ID:
57652836
MDL number:
MFCD00009835
Beilstein/REAXYS Number:
3629917
Concentration:
40% in THF
Form:
liquid
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form

liquid

Quality Level

200

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

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

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Danger

Hazard Classifications

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

supp_hazards

EUH014,EUH019

Storage Class

3 - Flammable liquids

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

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

target_organs

Central nervous system, Respiratory system

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBK7005
STBF5685V
STBF0524V
STBD9482V
STBD7989V

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Articles

New Multi-Dendrimer Platforms for Supramolecular Assembly

Dendrimers, polymer nanostructures, are synthesized for specific purposes by manipulating critical nanoscale design parameters (CNDPs).

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)
View All Related Papers

Global Trade Item Number

SKUGTIN
80631-500ML-F04061837675751
80631-5L-F04061837675768