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:
Product Name
Lithium diisopropylamide, 97%
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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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.
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.
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
Regulatory Information
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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)
Journal of Polymer Science Part A: Polymer Chemistry, 32, 2425-2425 (1994)
Aldrichimica Acta, 17, 80-80 (1984)
Lithium Diisopropylamide
Bakker WI, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Metalated Nitriles: Internal 1, 2-Asymmetric Induction
Fleming FF, et al.
Angewandte Chemie (International ed. in English), 46(37), 7098-7100 (2007)
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