Lithium Diisopropylamide CAS 4111-54-0

Lithium diisopropylamide (LDA) is a white pyrophoric powder. Freshly prepared, it is soluble in hydrocarbons (in hexane about 10 %), but it tends to precipitate irreversibly from solution as a polymer on heating or prolonged storage. In ethers the solubility is much higher, but with the exception of tetrahydropyran, LDA is decomposed at a rate depending on the ether, concentration, and temperature.

Lithium diisopropylamide is a sterically hindered nonnucleophilic strong base used for selective deprotonations, especially for the production of kinetic enolates (i.e., the thermodynamically less favored isomer) and (hetero-)aromatic carbanions. In the production of the serum lipid regulating agent Gemfibrozil one key intermediate is formed by quenching an ester enolate with 1-bromo-3-chloropropane.

Lithium diisopropylamide solution (LDA) can be used:

• As an initiator in the anionic polymerization of D,L-lactide and methyl methacrylate.
• To facilitate ester enolization.
• To convert carboxylic acids to enediolate intermediates for preparing trifluoromethyl ketones.
• In ortho-lithiation of arylsulfonyloxazolidinones to prepare N-substituted saccharin analogs.
• To catalyze ortholithiation and Fries rearrangement of aryl carbamates.
• As a promoter in the isomerization of allylic ethers to (Z)-propenyl ethers.

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Product Name:	Lithium diisopropylamide
Synonyms:	ithium diisopropyL;LITHIUM DIISOPROPYLAMIDE THF COMPLEX;LITHIUM DIISOPROPYLAMINE;LITHIUM DIISOPROPYLAMIDE;LDA THF COMPLEX;LDA;DIISOPROPYLAMINOLITHIUM;Lithium diisopropylamide solution
URUBANZA:	4111-54-0
MF:	C6H16LiN
MW:	109.14
EINECS:	223-893-0
Product Categories:	Classes of Metal Compounds;
Mol File:	4111-54-0.mol

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