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246611

Sigma-Aldrich

Lithium diisopropylamide

97%

Synonym(s):

LDA

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About This Item

Linear Formula:
[(CH3)2CH]2NLi
CAS Number:
4111-54-0
Molecular Weight:
107.12
Beilstein:
3655042
EC Number:
223-893-0
MDL number:
MFCD00064449
UNSPSC Code:
12352001
PubChem Substance ID:
24854817
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

100

Assay

97%

form

solid

density

0.864 g/mL at 25 °C (lit.)

functional group

amine

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.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H250,H314

Hazard Classifications

Eye Dam. 1 - Pyr. Sol. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 2: Flammable solids
Flammable solid
Hazardous rank III

JAN Code

246611-VAR:
246611-25G:
246611-BULK:
246611-100G-BULK:
246611-100G:
246611-25G-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK5395
SHBN1366
STBJ6778
STBJ1635
STBJ1636

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Journal of Polymer Science Part A: Polymer Chemistry, 32, 2425-2425 (1994)
Aldrichimica Acta, 17, 80-80 (1984)
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IEEE transactions on neural systems and rehabilitation engineering : a publication of the IEEE Engineering in Medicine and Biology Society, 23(4), 693-701 (2015-02-24)
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