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361798

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:

Molecular Weight:

107.12

UNSPSC Code:

12352001

NACRES:

NA.22

PubChem Substance ID:

MDL number:

Beilstein/REAXYS Number:

3655042

Concentration:

2.0 M in THF/heptane/ethylbenzene

Form:

liquid

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Properties

form

liquid

Quality Level

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

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pictograms

Flame

Health hazard

Corrosion

Exclamation mark

Environment

GHS02,GHS08,GHS05,GHS07,GHS09

signalword

Danger

hcodes

H225,H304,H314,H335,H336,H351,H373,H410

pcodes

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

supp_hazards

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

35.6 °F - closed cup

flash_point_c

2 °C - closed cup

Regulatory Information

危险化学品

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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)

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)

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Global Trade Item Number

SKU	GTIN
361798-100ML	04061831824513
361798-800ML	04061831824544
361798-4X100ML	04061831824520
361798-4X25ML	04061831824537
361798-PZ	04061823823418