361798

Lithium diisopropylamide solution

2.0 M in THF/heptane/ethylbenzene

• Synonym(s): LDA
• 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

Properties

• 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
• functional group: amine
• 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

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 Information

• Pictograms: GHS02,GHS08,GHS05,GHS07,GHS09
• Signal Word: Danger
• Hazard Statements: H225,H304,H314,H335,H336,H351,H373,H410
• Precautionary Statements: P210 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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