32579-76-3

Basic information

• Product Name: Piperidine,1-chloro-2,2,6,6-tetramethyl-
• Synonyms: Piperidine,1-chloro-2,2,6,6-tetramethyl-
• CAS NO: 32579-76-3
• Molecular Formula: C₉H₁₈ClN
• Molecular Weight: 175.6989
• Mol File: 32579-76-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 190.8°Cat760mmHg
• Flash Point: 69.2°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 0.53mmHg at 25°C
• Refractive Index: 1.478
• CAS DataBase Reference: Piperidine,1-chloro-2,2,6,6-tetramethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine,1-chloro-2,2,6,6-tetramethyl-(32579-76-3)
• EPA Substance Registry System: Piperidine,1-chloro-2,2,6,6-tetramethyl-(32579-76-3)

Safety Data

• Hazardous Substances Data: 32579-76-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 18, p. 2135, 1988 DOI: 10.1080/00397918808068284

InChI:InChI=1/C9H18ClN/c1-8(2)6-5-7-9(3,4)11(8)10/h5-7H2,1-4H3

Upstream product

• 768-66-1 2,2,6,6-tetramethyl-piperidine 

Downstream Products

• 768-66-1 2,2,6,6-Tetramethylpiperidiniumradikalkation 
• 2564-83-2 2,2,6,6-tetramethyl-piperidine-N-oxyl 
• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 74-87-3 methylene chloride 
• 112269-97-3 2,2,6-trimethyl-2,3,4,5-tetrahydropyridine 
• 111708-25-9 P-(2,2,6,6-tetramethylpiperidino)-N-(2,4,6-tri-tert-butylphenyl)phosphinimine 
• 125340-49-0 C₂₂H₄₁ClNPSi₂ 

Relevant articles and documents

Practical and Selective sp3 C?H Bond Chlorination via Aminium Radicals

The introduction of chlorine atoms into organic molecules is fundamental to the manufacture of industrial chemicals, the elaboration of advanced synthetic intermediates and also the fine-tuning of physicochemical and biological properties of drugs, agrochemicals and polymers. We report here a general and practical photochemical strategy enabling the site-selective chlorination of sp3 C?H bonds. This process exploits the ability of protonated N-chloroamines to serve as aminium radical precursors and also radical chlorinating agents. Upon photochemical initiation, an efficient radical-chain propagation is established allowing the functionalization of a broad range of substrates due to the large number of compatible functionalities. The ability to synergistically maximize both polar and steric effects in the H-atom transfer transition state through appropriate selection of the aminium radical has provided the highest known selectivity in radical sp3 C?H chlorination.

2,2,6,6-Tetramethylpiperidine-catalyzed, ortho-selective chlorination of phenols by sulfuryl chloride

2,2,6,6-Tetramethylpiperidine (TMP)-catalyzed (1- 10%) chlorinations of phenols by SO2Cl2 in aromatic solvents are more ortho selective than with primary and less hindered secondary amine catalysts. Ortho-selective chlorination is successful even with electron deficient phenols such as 2-hydroxybenzaldehyde and 2'- hydroxyacetophenone. Notably, ortho selectivity increases with the reaction temperature. On the other hand, tetraalkylammonium chloride-catalyzed chlorinations are moderately para selective.

Mechanism of electrochemical oxidation of 1-chloro-2,2,6,6- tetramethylpiperidine

In contrast to 2,2,6,6-tetramethylpiperidine and other aliphatic amines, at the electrochemical oxidation of 1-chloro-2,2,6,6-tetramethylpiperidine a sufficiently stable cation-radical is formed. Its formation is confirmed by the data of cyclic voltammetry and electron paramagnetic resonance. Further transformation of the cation-radical leads to the formation of 2,2,6,6-tetramethylpiperidin-1-oxyl.