dimer with THF: C1CCC[O+]1[Li-2]0[N+](C(C)C)(C(C)C)[Li-2]([O+]1CCCC1)[N+]0(C(C)C)C(C)C
Properties
Chemical formula
LiN(CH(CH3)2)2
Molar mass
107.1233 g/mol
Appearance
colourless solid
Density
0.79 g/cm3
Solubility in water
Reacts with water
Acidity (pKa)
36 (THF)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
corrosive
Related compounds
Related compounds
Superbases
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound
Lithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula LiN(CH(CH3)2)2. It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group.[2]
^Evans pKa Table
^Hamell, Matthew; Levine, Robert (1950). "Condensations Effected by the Alkali Amides. IV. The Reactions of Esters with Lithium Amide and Certain Substituted Lithium Amides1". The Journal of Organic Chemistry. 15: 162–168. doi:10.1021/jo01147a026.
and 24 Related for: Lithium diisopropylamide information
Lithiumdiisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula LiN(CH(CH3)2)2. It is used as a strong base and has...
cyclohexanyllithium. Common lithium amides, e.g. lithium bis(trimethylsilyl)amide and lithiumdiisopropylamide, are also subject to aggregation. Lithium amides adopt...
is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithiumdiisopropylamide, known as LDA is a widely used reagent. Diisopropylamine...
deprotonation is quantitative. Typically enolates are generated from using lithiumdiisopropylamide (LDA). Often, as in conventional Claisen condensations, Mannich...
carboxylate group can be converted to dianions with strong bases like lithiumdiisopropylamide. These react with alkyl halides to give derivatives:: 474 RCH2COO−...
enol ether is preferentially formed. For instance, when using lithiumdiisopropylamide (LDA), a strong and sterically hindered base, at low temperature...
stoichiometric and catalytic base. Using very strong bases like lithiumdiisopropylamide (LDA, pKa of conjugate acid ~36) under non-equilibrating conditions...
such. Like many lithium reagents it has a tendency to aggregate, forming a tetramer in the solid state. LithiumdiisopropylamideLithium amide amide primer...
superbase as a "compound having a very high basicity, such as lithiumdiisopropylamide." Superbases are often defined in two broad categories, organic...
with the chemical lithium amide itself as the parent structure. Common lithium amides include lithiumdiisopropylamide (LDA), lithium tetramethylpiperidide...
this solvent. Deprotonation of DMSO requires strong bases like lithiumdiisopropylamide and sodium hydride. Stabilization of the resultant carbanion is...
reaction of an allylic carboxylate with a strong base (such as lithiumdiisopropylamide) to give a γ,δ-unsaturated carboxylic acid. The rearrangement proceeds...
images Linear discriminant analysis, a type of statistical analysis Lithiumdiisopropylamide, a strong base in chemistry Local delivery agent, software that...
spectrometry Diisopropylamine, a common organic base and precursor to LithiumDiisopropylamide Diaa, a given name Diya (disambiguation) This disambiguation page...
than other cheap metals (lithium, aluminium, or magnesium). The following reaction gives a syn:anti ratio of 80:20 using a lithium enolate compared to 97:3...
osmium tetroxide, reducing agents such as lithium aluminium hydride, bases such as lithiumdiisopropylamide and acids such as sulfuric acid. Finally,...
and therefore more nucleophilic. Deprotonation with for instance lithiumdiisopropylamide (LDA) gives an azaenolate which can be alkylated by alkyl halides...
deprotonation should be done with extremely strong bases, such as lithiumdiisopropylamide. C ( NH 2 ) 3 + Cl − + Li + N ( C 3 H 7 ) 2 − ⟶ HNC ( NH 2 ) 2...
adjacent to the CN group. Strong bases are required, such as lithiumdiisopropylamide and butyl lithium. The product is referred to as a nitrile anion. These...
proton on indole. Reaction of N-protected indoles with butyl lithium or lithiumdiisopropylamide results in lithiation exclusively at the C2 position. This...
Ferrario reaction) is based on deprotonation of a tetrathiophene with lithiumdiisopropylamide followed by reaction with elemental sulfur to a sulfur-substituted...
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