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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

CAS-Nummer
1070-89-9
Synonyme
NaHMDS
N-Sodiohexamethyldisilazane

Größe Preis ($) Menge Verfügbarkeit
100ml 55,60
500ml 222,00
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Sodium bis(trimethylsilyl)amide, 2M soln. in THF

MDL
MFCD00009835
EINECS
213-983-8

Chemische Eigenschaften

Formel
C6H18NNaSi2
Molmasse
183.38
Flammpunkt
-17°(1°F)
Dichte
0.920
Sensitivität
Moisture Sensitive
Löslichkeit
Miscible with benzene and toluene.

Anwendungen

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.

Bemerkungen

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.

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H225-H314-H351-H335

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

Sicherheitshinweise: 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.

Weitere Referenzen

Beilstein
3629917
Gefahrenklasse
3
Verpackungsgruppe
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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