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361798

Sigma-Aldrich

Lithium diisopropylamide solution

2.0 M in THF/heptane/ethylbenzene

Synonym(s):

LDA

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100 ML
$190.00
4 X 25 ML
$232.00
4 X 100 ML
$492.00
800 ML
$652.00

$190.00


Estimated to ship on25 March 2025


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100 ML
$190.00
4 X 25 ML
$232.00
4 X 100 ML
$492.00
800 ML
$652.00

About This Item

Linear Formula:
[(CH3)2CH]2NLi
CAS Number:
Molecular Weight:
107.12
Beilstein:
3655042
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22
concentration:
2.0 M in THF/heptane/ethylbenzene

$190.00


Estimated to ship on25 March 2025


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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

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General description

Lithium diisopropylamide solution (LDA) is a sterically hindered non-nucleophilic strong base widely used in organic synthesis.[1]

Application

Lithium diisopropylamide solution (LDA) can be used:
  • As an initiator in the anionic polymerization of D,L-lactide and methyl methacrylate.[1]
  • To facilitate ester enolization.[2]
  • To convert carboxylic acids to enediolate intermediates for preparing trifluoromethyl ketones.[3]
  • In ortho-lithiation of arylsulfonyloxazolidinones to prepare N-substituted saccharin analogs.[4]
  • To catalyze ortholithiation and Fries rearrangement of aryl carbamates.[5]
  • As a promoter in the isomerization of allylic ethers to (Z)-propenyl ethers.[6]

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

35.6 °F - closed cup

Flash Point(C)

2 °C - closed cup


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Certificates of Analysis (COA)

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Trifluoromethyl ketones: properties, preparation, and application
Kelly CB, et al.
Chemical Communications (Cambridge, England), 49(95), 11133-11148 (2013)
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)
Isomerization of allyl ethers initiated by lithium diisopropylamide
Su C, and Williard PG
Organic Letters, 12(23), 5378-5381 (2010)
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)
Tetrahedron Letters, 47, 6405-6405 (2006)

Questions

1–3 of 3 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. Hi, can I know if it's ok to store LDA in THF/heptane/ethylbenzene or in THF/hexane, and nBuLi in Hexanes at -20 degrees celsius? Thanks!

    1 answer
    1. The recommended storage temperature for this product is 2 - 8 °C.

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