Lithium diisopropylamide

Lithium diisopropylamide
Names
	Preferred IUPAC name Lithium N-(propan-2-yl)propan-2-aminide
	Other names LDA
Identifiers
CAS Number	4111-54-0 ;
3D model (JSmol)	ionic form: Interactive image; covalent form: Interactive image; dimer with THF: Interactive image;
ChemSpider	2006804 ;
ECHA InfoCard	100.021.721
PubChem CID	2724682;
UNII	OL028KIW1I ;
CompTox Dashboard (EPA)	DTXSID6063305 ;
	InChI InChI=1S/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1 Key: ZCSHNCUQKCANBX-UHFFFAOYSA-N ; InChI=1/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1 Key: ZCSHNCUQKCANBX-UHFFFAOYAP;
	SMILES ionic form: [Li+].CC(C)[N-]C(C)C; covalent form: CC(C)N([Li])C(C)C; dimer with THF: C1CCC[O+]1[Li-2]0[N+](C(C)C)(C(C)C)[Li-2]([O+]1CCCC1)[N+]0(C(C)C)C(C)C;
Properties
Chemical formula	LiN(CH(CH3)2)2
Molar mass	107.1233 g/mol
Appearance	colourless solid
Density	0.79 g/cm3
Solubility in water	Reacts with water
Acidity (pKa)	36 (THF)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	corrosive
Related compounds
Related compounds	Superbases
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Lithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula LiN(CH(CH₃)₂)₂. It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group.^[2]

^ Evans pKa Table
^ Hamell, Matthew; Levine, Robert (1950). "Condensations Effected by the Alkali Amides. IV. The Reactions of Esters with Lithium Amide and Certain Substituted Lithium Amides1". The Journal of Organic Chemistry. 15: 162–168. doi:10.1021/jo01147a026.

[1] Evans pKa Table

[2] Hamell, Matthew; Levine, Robert (1950). "Condensations Effected by the Alkali Amides. IV. The Reactions of Esters with Lithium Amide and Certain Substituted Lithium Amides1". The Journal of Organic Chemistry. 15: 162–168. doi:10.1021/jo01147a026.

[1]

[2]