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Thermo Scientific Chemicals
2,2,6,6-Tetramethylpiperidine, 98+%
CAS: 768-66-1 | C9H19N | 141.258 g/mol
化学物質識別子
CAS768-66-1
IUPAC Name2,2,6,6-tetramethylpiperidine
Molecular FormulaC9H19N
InChI KeyRKMGAJGJIURJSJ-UHFFFAOYSA-N
SMILESCC1(C)CCCC(C)(C)N1
さらに表示
仕様
スペックシート
スペックシート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.
Applications
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.
Solubility
Miscible with water, ether, ethanol and acetic acid. Slightly miscible with chloroform.
Notes
Incompatible with oxidizing agents, bases, strong acids, acid anhydrides, carbon dioxide and acid chlorides.
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.
Solubility
Miscible with water, ether, ethanol and acetic acid. Slightly miscible with chloroform.
Notes
Incompatible with oxidizing agents, bases, strong acids, acid anhydrides, carbon dioxide and acid chlorides.
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.