246611

Sigma-Aldrich

Lithium diisopropylamide

97%

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

Quality Level

vapor density

>1 (vs air)

assay

97%

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.

Packaging

25, 100 g in glass bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3393 4.2(4.3)

WGK Germany

WGK 3

Flash Point(F)

10.4 °F - closed cup

Flash Point(C)

-12 °C - closed cup

Certificate of Analysis

Certificate of Origin

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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