Autorizzo l’utilizzo di cookies.

Accetto Utilizziamo cookies per migliorare il nostro servizio e realizzare statistiche. Questa funzione puó essere disattivata cambiando la configurazione del browser. Continuando a navigare senza modificare questi parametri, consideriamo che l’uso di cookies sia accettato

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

Codice CAS
1070-89-9
Sinonimi
NaHMDS
N-Sodiohexamethyldisilazane

Dimensioni Prezzo ($) Quantità Disponibilità
100ml 55,60
500ml 222,00
Aggiungi al carrello Aggiungi al preventivo generale Visualizza articolo

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

MDL
MFCD00009835
EINECS
213-983-8

Proprietà chimiche

Formula
C6H18NNaSi2
Peso formula
183.38
Punto di infiammabilità
-17°(1°F)
Densità
0.920
Sensibilità
Moisture Sensitive
Solubilità
Miscible with benzene and toluene.

Applicazioni

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.

Note

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.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (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.

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
3629917
Classe di rischio
3
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.90
TSCA
Yes

Raccomandato

Visualizzati di recente

Prodotti chimici

Scienze della vita

Metalli e materiali

Catalizzatori

Apparecchiature di analisi e di laboratorio