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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:
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

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

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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
GHS02,GHS05

signalword

Danger

hcodes

H250,H314

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

Certificates of Analysis (COA)

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Aldrichimica Acta, 17, 80-80 (1984)
Metalated Nitriles: Internal 1, 2-Asymmetric Induction
Fleming FF, et al.
Angewandte Chemie (International ed. in English), 46(37), 7098-7100 (2007)
Lithium Diisopropylamide
Bakker WI, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Journal of Polymer Science Part A: Polymer Chemistry, 32, 2425-2425 (1994)
KF/Al2O3 and PEG-400 as a recyclable medium for the selective ?-selenation of aldehydes and ketones. Preparation of potential antimicrobial agents
Victoria FN, et al.
Tetrahedron Letters, 50(49), 6761-6763 (2009)
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