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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

Numéro CAS
1070-89-9
Synonymes
NaHMDS
N-Sodiohexamethyldisilazane

Dimensions Prix ($) Quantité Disponibilité
100ml 48,60
500ml 194,40
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Sodium bis(trimethylsilyl)amide, 2M soln. in THF

MDL
MFCD00009835
EINECS
213-983-8

Propriétés chimiques

Formule
C6H18NNaSi2
Poids formulaire
183.38
Point d'éclair
-17°(1°F)
Densité
0.920
Sensibilité
Moisture Sensitive
Solubilité
Miscible with benzene and toluene.

Applications

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.

Notes

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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H225-H314-H351-H335

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Suspected of causing cancer. May cause respiratory irritation.

Mentions de prudence: P210-P260-P201-P261-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. 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. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3629917
Classe de danger
3
Groupe d'emballage
II
Code tarifaire harmonisé
2931.90
TSCA
Yes

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Analytique et matériel de laboratoire