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246611

Sigma-Aldrich

Lithium diisopropylamide

97%

Synonym(s):

LDA

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About This Item

Linear Formula:
[(CH3)2CH]2NLi
CAS Number:
Molecular Weight:
107.12
Beilstein/REAXYS Number:
3655042
EC Number:
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

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

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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.

pictograms

FlameCorrosion

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Pyr. Sol. 1 - Skin Corr. 1B

supp_hazards

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

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