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246611

Sigma-Aldrich

Lithium diisopropylamide

97%

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Synonym(s):
LDA
Linear Formula:
[(CH3)2CH]2NLi
CAS Number:
Molecular Weight:
107.12
Beilstein:
3655042
EC Number:
MDL number:
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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1 of 4

This Item
774766324620361798
assay

97%

assay

-

assay

97%

assay

-

form

solid

form

liquid

form

solid

form

liquid

density

0.864 g/mL at 25 °C (lit.)

density

0.719 g/mL at 25 °C

density

0.860 g/mL at 25 °C (lit.)

density

0.812 g/mL at 25 °C

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

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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)
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)
Aldrichimica Acta, 17, 80-80 (1984)

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