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L15012 Lithium bis(trimethylsilyl)amide, 20% (ca 1.06M) soln. in THF/ethylbenzene, packaged in resealable septum cap bottle

CAS Number
4039-32-1
Synonyms
LHMDS
Lithium hexamethyldisilazide

Stock No. Size Price ($) Quantity Availability
L15012-AE 100ml 83.70
L15012-AP 500ml 261.00
L15012-9Z 800ml 352.00
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Lithium bis(trimethylsilyl)amide, 20% (ca 1.06M) soln. in THF/ethylbenzene, packaged in resealable septum cap bottle

MDL
MFCD00008261
EINECS
223-725-6

Chemical Properties

Formula
C6H18LiNSi2
Formula Weight
167.33
Flash Point
-17°(1°F)
Density
0.891
Storage & Sensitivity
Moisture Sensitive. Air Sensitive. Store under Nitrogen. Ambient temperatures.
Solubility
Reacts with water.

Applications

Lithium bis(trimethylsilyl)amide is used in generating enolates for preparing lactone precursors, pyranones, and cyclohexanes. It is used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines and in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles. It is also used in the lithiation of ethyl acetate and in the stereospecific Wadsworth-Emmons synthesis of fluoroalkenes from (E)- and (Z)-fluorovinyl sulfones.

Notes

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. Store under inert gas. Incompatible with oxidizing agents.

Literature References

Bert Y. Kimura.; Theodore L. Brown. Solvent effects on the aggregation of lithium bis(trimethylsilyl)amide. Journal of Organometallic Chemistry. 1971, 26 (1), 57-67.

Sunwoo Lee.; Morten Jørgensen.; John F. Hartwig. Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides and Lithium Bis(trimethylsilyl)amide as an Ammonia Equivalent. Org. Lett. 2001, 3 (17), 2729-2732.

Supplied in septum cap bottle.

Versatile non-nucleophilic strong base. For examples of use in the lithiation of ethyl acetate, see: Org. Synth. Coll., 6, 598 (1988), and in the stereospecific Wadsworth-Emmons synthesis of fluoroalkenes from (E)- and (Z)-fluorovinyl sulfones: Org. Synth. Coll., 9, 442 (1998).

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H302-H304-H314-H335-H336-H351

Highly flammable liquid and vapour. Harmful if swallowed. May be fatal if swallowed and enters airways. Causes severe skin burns and eye damage. May cause respiratory irritation. May cause drowsiness or dizziness. Suspected of causing cancer.

Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P281-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c

Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
8136861
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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