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361798

Sigma-Aldrich

Lithium diisopropylamide solution

2.0 M in THF/heptane/ethylbenzene

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
MDL number:
MFCD00064449
UNSPSC Code:
12352001
PubChem Substance ID:
24862259
NACRES:
NA.22

form

liquid

Quality Level

200

concentration

2.0 M in THF/heptane/ethylbenzene

impurities

3 wt. % diisopropylamine

density

0.812 g/mL at 25 °C

storage temp.

2-8°C

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 solution (LDA) is a sterically hindered non-nucleophilic strong base widely used in organic synthesis.

Application

Lithium diisopropylamide solution (LDA) can be used:
  • As an initiator in the anionic polymerization of D,L-lactide and methyl methacrylate.
  • To facilitate ester enolization.
  • To convert carboxylic acids to enediolate intermediates for preparing trifluoromethyl ketones.
  • In ortho-lithiation of arylsulfonyloxazolidinones to prepare N-substituted saccharin analogs.
  • To catalyze ortholithiation and Fries rearrangement of aryl carbamates.
  • As a promoter in the isomerization of allylic ethers to (Z)-propenyl ethers.

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system, hearing organs, Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

35.6 °F - closed cup

Flash Point(C)

2 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lithium diisopropylamide-mediated enolizations: Solvent-dependent mixed aggregation effects
Sun X and Collum DB
Journal of the American Chemical Society, 122(11), 2459-2463 (2000)
Anionic polymerization of D, L-lactide initiated by lithium diisopropylamide
Bhaw-Luximon A, et al.
Polymer, 42(24), 9651-9656 (2001)
Trifluoromethyl ketones: properties, preparation, and application
Kelly CB, et al.
Chemical Communications (Cambridge, England), 49(95), 11133-11148 (2013)
Isomerization of allyl ethers initiated by lithium diisopropylamide
Su C, and Williard PG
Organic Letters, 12(23), 5378-5381 (2010)
Efficient access to chiral N-substituted saccharin analogues via the directed ortho-lithiation of 3-N-arylsulfonyloxazolidin-2-ones
Aliyenne AO, et al.
Tetrahedron Letters, 47(36), 6405-6408 (2006)
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