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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

CAS Number
40949-94-8
Synonyms
KHMDS
Potassium hexamethyldisilazide

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

MDL
MFCD00010330
EINECS
424-100-2

Chemical Properties

Formula
C6H18KNSi2
Formula Weight
199.49
Flash Point
7°(44°F)
Density
0.881
Refractive Index
1.4900
Sensitivity
Air & Moisture Sensitive
Solubility
Reacts with water.

Applications

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.

Notes

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.

Literature References

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H304-H361-H373-H314-H336

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

Precautionary Statements: P210-P260-P201-P261-P301+P310-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. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
4006754
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
No

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