246611

Lithium diisopropylamide

97%

• Synonym(s): LDA
• Linear Formula: [(CH₃)₂CH]₂NLi
• CAS Number: 4111-54-0
• Molecular Weight: 107.12
• Beilstein/REAXYS Number: 3655042
• EC Number: 223-893-0
• MDL number: MFCD00064449
• UNSPSC Code: 12352001
• PubChem Substance ID: 24854817
• NACRES: NA.22

Properties

• vapor density: >1 (vs air)
• assay: 97%
• form: solid
• density: 0.864 g/mL at 25 °C (lit.)
• SMILES string: [Li]N(C(C)C)C(C)C
• InChI: 1S/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1
• InChI key: ZCSHNCUQKCANBX-UHFFFAOYSA-N

Description

General description

Lithium diisopropylamide (LDA) is a hindered non-nucleophilic strong base that abstracts hydrogen from active carbon. It can be prepared from diisopropylamine and butyllithium in the presence of tetrahydrofuran.

Application

Lithium diisopropylamide can be used for the generation of carbanion or enolate anions from carbonyl group-containing compounds.
It can also be used as a base in:

• The direct alkylation and acylation of ketones.
• The aldol condensation reaction.
• α-Selenation reaction.
• The synthesis of α, β- unsaturated carbonyl compounds from carbonyl compounds.
• The alkylation of acids, esters, amides, and nitriles.
• The initiation of anionic polymerization.

Safety Information

• pictograms: GHS02,GHS05
• signalword: Danger
• hcodes: H250,H314
• pcodes: P231 + P232 - P260 - P280 - P303 + P361 + P353 - P305 + P351 + P338 - P370 + P378
• Hazard Classifications: Eye Dam. 1 - Pyr. Sol. 1 - Skin Corr. 1B
• supp_hazards: EUH014
• Storage Class: 4.2 - Pyrophoric and self-heating hazardous materials
• wgk_germany: WGK 2
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges