26684-56-0

Basic information

• Product Name: 4-(tetrahydro-2H-pyran-4-yl)pyridine
• CAS NO: 26684-56-0
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.2163
• Mol File: 26684-56-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 269.4°C at 760 mmHg
• Flash Point: 98.7°C
• Density: 1.053g/cm³
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: 4-(tetrahydro-2H-pyran-4-yl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(tetrahydro-2H-pyran-4-yl)pyridine(26684-56-0)
• EPA Substance Registry System: 4-(tetrahydro-2H-pyran-4-yl)pyridine(26684-56-0)

Safety Data

• Hazardous Substances Data: 26684-56-0(Hazardous Substances Data)

Upstream product

• 75-21-8 oxirane 
• 108-89-4 picoline 
• 7782-61-8 ferric nitrate 
• 25637-16-5 4-bromotetrahydro-2H-pyran 
• 19524-06-2 4-bromopyridine hydrochloride 
• 1120-87-2 4-bromopyridin 
• 59137-44-9 3-carboxy-2-(pyridin-1-ium-1-yl)propanoate 
• 110-86-1 pyridine 

Relevant articles and documents

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.

General C(sp2)-C(sp3) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts

Cross-electrophile coupling (XEC) of alkyl and aryl halides promoted by electrochemistry represents an attractive alternative to conventional methods that require stoichiometric quantities of high-energy reductants. Most importantly, electroreduction can readily exceed the reducing potentials of chemical reductants to activate catalysts with improved reactivities and selectivities over conventional systems. This work details the mechanistically-driven development of an electrochemical methodology for XEC that utilizes redox-active shuttles developed by the energy-storage community to protect reactive coupling catalysts from overreduction. The resulting electrocatalytic system is practical, scalable, and broadly applicable to the reductive coupling of a wide range of aryl, heteroaryl, or vinyl bromides with primary or secondary alkyl bromides. The impact of overcharge protection as a strategy for electrosynthetic methodologies is underscored by the dramatic differences in yields from coupling reactions with added redox shuttles (generally >80%) and those without (generally 20%). In addition to excellent yields for a wide range of substrates, reactions protected from overreduction can be performed at high currents and on multigram scales.

Pyridyl-tetrahydropyrans and process for preparing same

The present invention deals with intermediate compounds, namely 4-(2'-, 3'- and 4'-pyridyl)-tetrahydropyrans and a process for their preparation. These compounds are prepared by reacting a 2'-haloethyl-3-(pyridyl)propyl ether with an alkali metal amide at