67286-76-4

Basic information

• Product Name: ethyl (2Z)-2-(phenylhydrazono)-3-(1H-pyrrol-1-yl)propanoate
• CAS NO: 67286-76-4
• Molecular Formula: C₁₅H₁₇N₃O₂
• Molecular Weight: 271.3144
• Mol File: 67286-76-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 397.2°C at 760 mmHg
• Flash Point: 194°C
• Density: 1.12g/cm³
• Vapor Pressure: 1.62E-06mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: ethyl (2Z)-2-(phenylhydrazono)-3-(1H-pyrrol-1-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2Z)-2-(phenylhydrazono)-3-(1H-pyrrol-1-yl)propanoate(67286-76-4)
• EPA Substance Registry System: ethyl (2Z)-2-(phenylhydrazono)-3-(1H-pyrrol-1-yl)propanoate(67286-76-4)

Safety Data

• Hazardous Substances Data: 67286-76-4(Hazardous Substances Data)

Upstream product

• 369-57-3 benzenediazonium tetrafluoroborate 
• 81239-20-5 (E)-3-(2,5-Dihydro-pyrrol-1-yl)-acrylic acid ethyl ester 

Relevant articles and documents

BASE-CATALYZED TRANSFORMATIONS OF IMINIUM PHENYLHYDRAZONES. A NEW CONVENIENT SYNTHESIS OF IMIDAZOAZACYCLOALKANES

β-Enamine esters react with phenyldiazonium fluoroborate to give iminium phenylhydrazone salts which, without isolation, can be converted by a base-catalysed reaction to imidazole derivatives.The latter reaction is critically dependent upon the nature of the base-component of the enamine ester.The mechanism of imidazole formation involves the following sequence of steps: (a) deprotonation of the iminium salt, (b) a symmetry-allowed 1,5-dipolar cyclization of the betaine intermediate and (c) subsequent elimination of aniline, whith concomitant aromatization.The scope of the reaction as a facile approach to the synthesis of imidazole derivatives is discussed.