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40949-94-8 - Potassium bis(trimethylsilyl)amide, 15% w/w in toluene - KHMDS - Potassium hexamethyldisilazide - L15022 - Alfa Aesar

L15022 Potassium bis(trimethylsilyl)amide, 15% w/w in toluene

Número CAS
40949-94-8
Nombre Alternativo
KHMDS
Potassium hexamethyldisilazide

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Potassium bis(trimethylsilyl)amide, 15% w/w in toluene

MDL
MFCD00010330
EINECS
424-100-2

Propiedades químicas

Fórmula
C6H18KNSi2
Peso molecular
199.49
Punto de inflamabilidad
7°(44°F)
Densidad
0.881
Índice de refracción
1.4900
Sensibilidad
Air & Moisture Sensitive
Solubilidad
Reacts with water.

Aplicaciones

Potassium bis(trimethylsilyl)amide is used in the generation of K enolates. It is also used in the Wittig reaction, to give Li salt-free product distribution for selective (Z)-alkene formation and used with 18-crown-6 for selective formation of (Z)-?ß-unsaturated esters from phosphonates.

Notas

It is sensitive to moisture and air. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Handle and store under inert gas. Incompatible with strong oxidizing agents.

Referencias documentales

Kris F. Tesh.; Timothy P. Hanusa.; John C. Huffman. Ion pairing in [bis(trimethylsilyl)amido]potassium: The x-ray crystal structure of unsolvated [KN(SiMe3)2]2. Inorg. Chem. 1990, 29 (8), 1584-1586 .

Jörg Brüning. Lithium and potassium bis(trimethylsilyl)amide: Utilizing non-nucleophilic bases as nitrogen sources. Tetrahedron Letters. 1997, 38 (18), 3187-3188.

Sterically hindered strong base, compare Sodium bis(trimethyl­silyl)­amide, L13352 and Lithium bis(trimethyl­silyl)­amide, L15012. Used in the generation of K enolates, preferred to their Li or Na counterparts in some reactions, see e.g.: Tetrahedron Lett., 32, 1779 (1991); J. Am. Chem. Soc., 109, 6881 (1987); 111, 1063 (1989).

Also used in the Wittig reaction, to give Li salt-free product distribution for selective (Z)-alkene formation: J. Org. Chem., 45, 4260 (1980). Has also been used with 18-crown-6 for selective formation of (Z)-ɑß-unsaturated esters from phosphonates: Tetrahedron Lett., 24, 4405 (1983).

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H225-H302-H333-H314-H318-H361-H336-H373-H304

Highly flammable liquid and vapour. Harmful if swallowed. May be harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of damaging fertility or the unborn child. May cause drowsiness or dizziness. May cause damage to organs through prolonged or repeated exposure. May be fatal if swallowed and enters airways.

Indicaciones de precaución: P210-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: 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
4006754
Clase de peligro
3
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2931.90
TSCA
No

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