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361798 Sigma-Aldrich

Lithium diisopropylamide solution

2.0 M in THF/heptane/ethylbenzene

Synonym: LDA

  • CAS Number 4111-54-0

  • Linear Formula [(CH3)2CH]2NLi

  • Molecular Weight 107.12

  •  Beilstein/REAXYS Number 3655042

  •  MDL number MFCD00064449

  •  PubChem Substance ID 24862259

  •  NACRES NA.22

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Properties

Related Categories 25mL Sure/Seal Reagents, Acids & Bases, Bases, Chemical Synthesis, Organic Bases,
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

Description

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

4×25, 100, 4×100, 800 mL in Sure/Seal™

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

Safety & Documentation

Safety Information

Signal word 
Danger
Target organs 
hearing organs
Supplemental Hazard Statements 
EUH014 - EUH018 - EUH019
RIDADR 
UN3399 - class 4.3 - PG 2 - EHS - Organometallic substance, liquid, water-reactive, flammable, HI: all (not BR)
WGK Germany 
WGK 3
Flash Point(F) 
35.6 °F - closed cup
Flash Point(C) 
2 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Acids and Bases

Acids and bases have been used by chemists for centuries, and are among the most fundamental reagents employed in synthetic organic chemistry. This product line ranges from Brønsted and Lewis acids, ...
Chemfiles Volume 1 Article 3

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References

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