2,2,6,6-Tetrametilpiperidina, +98 %, Thermo Scientific Chemicals

Name: 2,2,6,6-Tetrametilpiperidina, +98 %, Thermo Scientific Chemicals
SKU: A18712.14

CAS: 768-66-1 | C9H19N | 141.258 g/mol

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Cantidad:

5 g

25 g

100 g

Número de catálogo A18712.14

también denominado A18712-14

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Cantidad:

25 g

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Identificadores químicos

CAS768-66-1

IUPAC Name2,2,6,6-tetramethylpiperidine

Molecular FormulaC9H19N

InChI KeyRKMGAJGJIURJSJ-UHFFFAOYSA-N

SMILESCC1(C)CCCC(C)(C)N1

Especificaciones Specification Sheet

Hoja de especificaciones

Refractive Index1.4425-1.4465 @ 20°C

Appearance (Color)Clear colorless to yellow to orange to pale brown

Assay (GC)≥98.0%

Identification (FTIR)Conforms

FormLiquid

2,2,6,6-Tetramethylpiperidine is a hindered base used to prepare metallo-amide bases and selective generation of silylketene acetals. It is used in the preparation of hibarimicinone, (Z)-silylketene acetal and 4-substituted quinazoline. It acts as a precursor to Lithium tetramethylpiperidide and (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl radical.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Aplicaciones
La 2,2,6,6-tetrametilpiperidina es una base impedida que se utiliza para preparar bases de metaloamida y la generación selectiva de acetales de sililceteno. Se utiliza en la preparación de la hibarimicinona, acetal de (Z)-sililceteno y quinazolina 4-substituida. Actúa como precursor de la tetrametilpiperidina de litio y el radical (2,2,6,6-tetrametilpiperidina-1-il)oxil.

Solubilidad
Miscible con agua, éter, etanol y ácido acético. Ligeramente miscible con cloroformo.

Notas
Incompatible con agentes oxidantes, bases, ácidos fuertes, anhídridos ácidos, dióxido de carbono y cloruros ácidos.

RUO – Research Use Only

General References:

Lithiation gives a highly-hindered, non-nucleophilic strong base; see, e.g. Org. Synth. Coll., 6, 571 (1988); 9, 426 (1998); Tetrahedron, 50, 3099 (1994). For use in selective isomerization of epoxides to aldehydes, see: J. Chem. Soc., Chem. Commun., 2103 (1994). For a study of the influence of TMEDA and related chelating ligands on the solution structure of the lithiated base, see: J. Org. Chem., 62, 5748 (1997). The Mg derivative, obtained by reaction with n-BuMgCl, is also an effective strong base which has been used in the regioselective ortho-metallation of pyridine carbamates and carboxamides: J. Org. Chem., 60, 8414 (1995).
Walker, W. K.; Kay, B. M.; Michaelis, S. A.; Anderson, D. L.; Smith, S. J.; Ess, D. H.; Michaelis, D. J. Origin of Fast Catalysis in Allylic Amination Reactions Catalyzed by Pd-Ti Heterobimetallic Complexes. J. Am. Chem. Soc. 2015, 137 (23), 7371-7378.
Longobardi, L. E.; Mahdi, T.; Stephan, D. W. B(C₆F₅)₃ mediated arene hydrogenation/transannulation of para-methoxyanilines. Dalton Trans. 2015, 44 (16), 7114-7117.