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1070-89-9 - Sodium bis(trimethylsilyl)amide, 2M soln. in THF - NaHMDS - N-Sodiohexamethyldisilazane - L13352 - Alfa Aesar

L13352 Sodium bis(trimethylsilyl)amide, 2M soln. in THF

Número CAS
1070-89-9
Nombre Alternativo
NaHMDS
N-Sodiohexamethyldisilazane

Tamaño Precio ($) Cantidad Disponibilidad
100ml 55,60
500ml 222,00
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Sodium bis(trimethylsilyl)amide, 2M soln. in THF

MDL
MFCD00009835
EINECS
213-983-8

Propiedades químicas

Fórmula
C6H18NNaSi2
Peso molecular
183.38
Punto de inflamabilidad
-17°(1°F)
Densidad
0.920
Sensibilidad
Moisture Sensitive
Solubilidad
Miscible with benzene and toluene.

Aplicaciones

Sodium bis(trimethylsilyl)amide is a strong base used in organic synthesis for deprotonation reactions and base catalyzed reaction. It is also used to enhance the polymerization of pheneylacetylene in conjunction with rhodium(I) catalysis. It is involved in the generation of enolates, Wittig reagents and carbenes.

Notas

Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents, strong oxidizing agents and oxygen. Dry residue is explosive.

Referencias documentales

Useful sterically hindered base (NaHMDS) for, e.g. generation of enolates, Wittig reagents or carbenes.

Used as a base for the preparation of ester enolates: J. Am. Chem. Soc., 93, 4945 (1971). Has been found to be superior to LDA for preparation of (Z)-enolates of ketones under thermodynamic control: Tetrahedron Lett., 30, 2779 (1989).

In the Wittig reaction, gives Li salt-free product distribution patterns, with selective (Z)-alkene formation: Chem. Ber., 109, 1694 (1976); Tetrahedron Lett., 30, 2173 (1989). For formation of anions of benzylic phosphonates and subsequent ɑɑ-difluorination, see N-Fluorobenzenesulfonimide, L13955.

Found to give better yields than LiHMDS or KHMDS for the carbenoid reactions with Dibromomethane, A10456: Synthesis, 201 (1972); Angew. Chem. Int. Ed., 11, 326 (1972).

Sufficiently nucleophilic to act as a protected form of ammonia in the synthesis of primary amines from halides and tosylates: Chem. Ber., 117, 1250 (1984).

Lis, A. V.; Tsyrendorzhieva, I. P.; Albanov, A. I.; Shainyan, B. A.; Rakhlin, V. I. Reaction of sodium bis(trimethylsilyl) amide with bromotoluenes. Russ. J. Org. Chem. 2015, 51 (3), 335-340.

Block, M.; Bette, M.; Wagner, C.; Schmidt, J.; Steinborn, D. Rhodium(I) complexes with κP coordinated ω-phosphinofunctionalized alkyl phenyl sulfide, sulfoxide and sulfone ligands and their reactions with sodium bis (trimethylsilyl) amide and Ag [BF4]. J. Org. Chem. 2011, 696 (9), 1768-1781.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H225-H303-H333-H314-H318-H351-H335

Highly flammable liquid and vapour. May be harmful if swallowed. May be harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of causing cancer. May cause respiratory irritation.

Indicaciones de precaución: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
3629917
Clase de peligro
3
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2931.90
TSCA
Yes

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