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4039-32-1 - Lithium bis(trimethylsilyl)amide, 20% (ca 1.06M) soln. in THF/ethylbenzene, packaged in resealable septum cap bottle - LHMDS - Lithium hexamethyldisilazide - L15012 - Alfa Aesar

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

Size Price ($) Quantity Availability
100ml 72.45
500ml 200.80
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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
Sensitivity
Air & Moisture Sensitive
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-H314-H351-H335-H333

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

Precautionary Statements: 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.

Other References

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

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