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Details

Stereochemistry ACHIRAL
Molecular Formula C6H14N.Li
Molecular Weight 107.123
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LITHIUM DIISOPROPYLAMIDE

SMILES

[Li+].CC(C)[N-]C(C)C

InChI

InChIKey=ZCSHNCUQKCANBX-UHFFFAOYSA-N
InChI=1S/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1

HIDE SMILES / InChI

Molecular Formula C6H15N
Molecular Weight 101.19
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Li
Molecular Weight 6.941
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.fmclithium.com/Portals/FMCLithium/content/docs/DataSheet/QS-PDS-047%20r1.pdf

Lithium diisopropylamide (LDA) is a prominent reagent used in organic synthesis. It is strong, low-nucleophilic base for e.g. enolisations. Corrosive to the eyes (may cause blindness), skin, mucous membranes and upper respiratory tract. Inhalation of vapors may cause dizziness, nausea, anesthesia, numbness, motor weakness in fingers and toes, incoordination, and headache.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Lithium Diisopropylamide: Nonequilibrium Kinetics and Lessons Learned about Rate Limitation.
2017-05-05
Sodium Diisopropylamide in N,N-Dimethylethylamine: Reactivity, Selectivity, and Synthetic Utility.
2016-11-18
One-Pot Halogen Dance/Negishi Coupling of Dibromothiophenes for Regiocontrolled Synthesis of Multiply Arylated Thiophenes.
2016-11-07
Lithium Enolates Derived from Pyroglutaminol: Mechanism and Stereoselectivity of an Azaaldol Addition.
2016-08-17
Lithium diisopropylamide: solution kinetics and implications for organic synthesis.
2007
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:19:32 GMT 2025
Edited
by admin
on Mon Mar 31 21:19:32 GMT 2025
Record UNII
OL028KIW1I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIISOPROPYLAMINE LITHIUM SALT
MI  
Preferred Name English
LITHIUM DIISOPROPYLAMIDE
Systematic Name English
DIISOPROPYLAMINE LITHIUM SALT [MI]
Common Name English
LDA
Common Name English
LITHIODIISOPROPYLAMINE
Systematic Name English
Code System Code Type Description
FDA UNII
OL028KIW1I
Created by admin on Mon Mar 31 21:19:32 GMT 2025 , Edited by admin on Mon Mar 31 21:19:32 GMT 2025
PRIMARY
WIKIPEDIA
LITHIUM DIISOPROPYLAMIDE
Created by admin on Mon Mar 31 21:19:32 GMT 2025 , Edited by admin on Mon Mar 31 21:19:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID6063305
Created by admin on Mon Mar 31 21:19:32 GMT 2025 , Edited by admin on Mon Mar 31 21:19:32 GMT 2025
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PUBCHEM
2724682
Created by admin on Mon Mar 31 21:19:32 GMT 2025 , Edited by admin on Mon Mar 31 21:19:32 GMT 2025
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MERCK INDEX
m4485
Created by admin on Mon Mar 31 21:19:32 GMT 2025 , Edited by admin on Mon Mar 31 21:19:32 GMT 2025
PRIMARY Merck Index
CAS
4111-54-0
Created by admin on Mon Mar 31 21:19:32 GMT 2025 , Edited by admin on Mon Mar 31 21:19:32 GMT 2025
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ECHA (EC/EINECS)
223-893-0
Created by admin on Mon Mar 31 21:19:32 GMT 2025 , Edited by admin on Mon Mar 31 21:19:32 GMT 2025
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