82126-20-3

Basic information

• Product Name: 1(4H)-Pyridinecarboxylic acid, 4-phenyl-, ethyl ester
• CAS NO: 82126-20-3
• Molecular Formula: C14H15NO2
• Molecular Weight: 229.279
• Mol File: 82126-20-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1(4H)-Pyridinecarboxylic acid, 4-phenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1(4H)-Pyridinecarboxylic acid, 4-phenyl-, ethyl ester(82126-20-3)
• EPA Substance Registry System: 1(4H)-Pyridinecarboxylic acid, 4-phenyl-, ethyl ester(82126-20-3)

Safety Data

• Hazardous Substances Data: 82126-20-3(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 541-41-3 chloroformic acid ethyl ester 
• 3958-47-2 triphenylindium 
• 63755-30-6 N-ethoxycarbonylpyridinium chloride 
• 100-59-4 phenylmagnesium chloride 

Downstream Products

• 939-23-1 p-phenylpyridine 
• 623-53-0 ethyl methyl carbonate 

Relevant articles and documents

Copper-Catalyzed multicomponent coupling of organoindium reagents with nitrogen-Containing aromatic heterocycles

A mild, copper-catalyzed coupling of organoindium reagents with nitrogen-containing aromatic heterocycles and chloroformates is described. This reaction proceeds with a range of organoindium reagents, yielding predominately or exclusively the 1,4-addition products with pyridine. In addition, a range of other nitrogen-containing heterocycles can be employed in this reaction (e.g. benzoxazole, benzothiazole, phthalazine). As an illustration of the utility of this reaction, this heterocycle functionalization is coupled with a subsequent oxidation to achieve the one-pot synthesis of functionalized pyridine and benzothiazole derivatives.

A Convenient Method for the Regioselective Synthesis of 4-Alkyl(aryl)pyridines Using Pyridinium Salts

RCu.BF3 reacted with 1-ethocycarbonylpyridinium chloride at the 4-position with almost complete regioselectivity (>99percent) to afford the corresponding 1,4-dihydropyridine derivatives in high yields (81-94percent).The dihydropyridines were oxidized by oxygen to give 4-alkyl(aryl)pyridines (38-68percent).Grignard reagents also reacted with 1-t-butyldimethylsilylpyridinium triflate with almost complete regioselectivity (>99percent) to afford the corresponding 1,4-dihydropyridines, which were easily oxidized to give 4-substituted pyridines in higher yields than above (58-70percent).

REGIOSELECTIVE SYNTHESIS OF 4-ALKYLPYRIDINES VIA 1,4-DIHYDROPYRIDINE DERIVATIVES FROM PYRIDINE

N-Ethoxycarbonylpyridinium chloride (1) reacted with at 4-position with almost complete regioselectivity (better than 99percent) to afford the corresponding 1,4-dihydropyridine derivatives (2) in high yields (81 ca. 94percent).The dihydropyridines were readily oxidized by oxygen to give 4-alkylpyridines (4:38 ca. 68percent yields).