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361798

Lithium diisopropylamide solution

2.0 M in THF/heptane/ethylbenzene

Synonym(s):

LDA

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Pack SizeSKUAvailabilityPrice
4 x 25 mL
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$72.30
100 mL
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$77.30
4 x 100 mL
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$276.00
800 mL
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$278.00

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

$72.30


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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

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.[1]
  • 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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1 of 1

This Item
225770774766577928
concentration

2.0 M in THF/heptane/ethylbenzene

concentration

1.0 M in THF

concentration

1.0 M in THF/hexanes

concentration

1 M in toluene

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

liquid

form

liquid

form

liquid

form

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

density

0.812 g/mL at 25 °C

density

0.891 g/mL at 25 °C

density

0.719 g/mL at 25 °C

density

0.860 g/mL at 25 °C

impurities

3 wt. % diisopropylamine

impurities

-

impurities

-

impurities

-


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signalword

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

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



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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)
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)
Isomerization of allyl ethers initiated by lithium diisopropylamide
Su C, and Williard PG
Organic Letters, 12(23), 5378-5381 (2010)



Global Trade Item Number

SKUGTIN
361798-800ML04061831824544
361798-100ML04061831824513
361798-4X25ML04061831824537
361798-4X100ML04061831824520

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/418/501/product-dating-information-06-25-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.

      Helpful?

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