246611
Lithium diisopropylamide
97%
Synonym(s):
LDA
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About This Item
Linear Formula:
[(CH3)2CH]2NLi
CAS Number:
Molecular Weight:
107.12
UNSPSC Code:
12352001
NACRES:
NA.22
PubChem Substance ID:
EC Number:
223-893-0
Beilstein/REAXYS Number:
3655042
MDL number:
Assay:
97%
Form:
solid
InChI key
ZCSHNCUQKCANBX-UHFFFAOYSA-N
InChI
1S/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1
SMILES string
[Li]N(C(C)C)C(C)C
vapor density
>1 (vs air)
assay
97%
form
solid
density
0.864 g/mL at 25 °C (lit.)
functional group
amine
Quality Level
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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:
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Pyr. Sol. 1 - Skin Corr. 1B
supp_hazards
Storage Class
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 2
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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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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