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246611

Sigma-Aldrich

Lithium diisopropylamide

97%

Synonym(s):

LDA

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25 G
$428.00
100 G
$876.85

$428.00

Estimated to ship onApril 12, 2025

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25 G
$428.00
100 G
$876.85

About This Item

Linear Formula:
[(CH3)2CH]2NLi
CAS Number:
4111-54-0
Molecular Weight:
107.12
Beilstein/REAXYS Number:
3655042
EC Number:
223-893-0
MDL number:
MFCD00064449
UNSPSC Code:
12352001
PubChem Substance ID:
24854817
NACRES:
NA.22

$428.00

Estimated to ship onApril 12, 2025

Request a Bulk Order

vapor density

>1 (vs air)

Quality Level

100

assay

97%

form

solid

density

0.864 g/mL at 25 °C (lit.)

functional group

amine

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 (LDA) is a hindered non-nucleophilic strong base that abstracts hydrogen from active carbon. It can be prepared from diisopropylamine and butyllithium in the presence of tetrahydrofuran.[1]

Application

Lithium diisopropylamide can be used for the generation of carbanion or enolate anions from carbonyl group-containing compounds.[1]
It can also be used as a base in:
  • The direct alkylation and acylation of ketones.[1]
  • The aldol condensation reaction.[1]
  • α-Selenation reaction.[2]
  • The synthesis of α, β- unsaturated carbonyl compounds from carbonyl compounds.[1]
  • The alkylation of acids, esters, amides, and nitriles.[1][3]
  • The initiation of anionic polymerization.[4]

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H250,H314

Hazard Classifications

Eye Dam. 1 - Pyr. Sol. 1 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 2

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3904
STBL3859
SHBR7693
SHBQ4772
STBK5395

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Aldrichimica Acta, 17, 80-80 (1984)
Lithium Diisopropylamide
Bakker WI, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Metalated Nitriles: Internal 1, 2-Asymmetric Induction
Fleming FF, et al.
Angewandte Chemie (International ed. in English), 46(37), 7098-7100 (2007)
Journal of Polymer Science Part A: Polymer Chemistry, 32, 2425-2425 (1994)
KF/Al2O3 and PEG-400 as a recyclable medium for the selective ?-selenation of aldehydes and ketones. Preparation of potential antimicrobial agents
Victoria FN, et al.
Tetrahedron Letters, 50(49), 6761-6763 (2009)
View All Related Papers

Questions

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  1. 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

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  2. 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

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