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:
Molecular Weight:
183.37
Beilstein:
3629917
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22
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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. 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
Precautionary Statements
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
Target Organs
Respiratory system
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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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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