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Sigma-Aldrich

Lithium 2,2,6,6-tetramethylpiperidide

95%

Synonyme(s) :

2,2,6,6-Tetramethylpiperidine lithium salt (1:1), LTMP

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About This Item

Formule empirique (notation de Hill) :
C9H18LiN
Numéro CAS:
Poids moléculaire :
147.19
Numéro MDL:
Code UNSPSC :
12352005
ID de substance PubChem :
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Essai

95%

Forme

solid

Chaîne SMILES 

[Li]N1C(C)(C)CCCC1(C)C

InChI

1S/C9H18N.Li/c1-8(2)6-5-7-9(3,4)10-8;/h5-7H2,1-4H3;/q-1;+1

Clé InChI

ANYSGBYRTLOUPO-UHFFFAOYSA-N

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Application

Lithium 2,2,6,6-tetramethylpiperidide is a strong base and can be used:
  • For the synthesis of enamines from terminal epoxides through trans-α-lithiated epoxide as an intermediate.[1]
  • For ortholithiation of arenes such as 1,3-bis(trifluoromethyl)benzene, 4,4-dimethyl-2-phenyl-2-oxazoline, 1,4-bis(trifluoromethyl)benzene and 1,3-dimethoxybenzene.[2]
  • In combination with Lewis donor ligand, N,N,N′,N′-tetramethylethylenediamine (TMEDA) for deprotonative metalation of methoxy-substituted arenes.{21]

Pictogrammes

FlameCorrosion

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

Skin Corr. 1B - Water-react 2

Code de la classe de stockage

4.3 - Hazardous materials which set free flammable gases upon contact with water

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Certificats d'analyse (COA)

Lot/Batch Number

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Consulter la Bibliothèque de documents

Case for Lithium Tetramethylpiperidide-Mediated Ortholithiations: Reactivity and Mechanisms.
Mack KA and Collum DB
Journal of the American Chemical Society, 140(14), 4877-4883 (2018)
Alkenes from terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide and organolithiums or grignard reagents.
Hodgson DM, et al.
Journal of the American Chemical Society, 126(39), 12250-12251 (2004)
Deprotonative metalation of methoxy-substituted arenes using lithium 2, 2, 6, 6-tetramethylpiperidide: Experimental and computational study.
Akimoto G, et al.
The Journal of Organic Chemistry, 83(21), 13498-13506 (2018)
Martin-Louis Y Riu et al.
Science advances, 6(13), eaaz3168-eaaz3168 (2020-04-02)
This exploratory synthesis investigation was undertaken to determine the viability of replacing a single carbon vertex with another p-block element in a highly strained tetrahedrane molecule. Phosphorus was selected for this purpose because the stable molecular form of elemental phosphorus

Questions

1–2 of 2 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

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  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

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