57322-50-6

Basic information

• Product Name: N-ETHYL-N-(4-PICOLYL)ATROPAMIDE
• Synonyms: N-ETHYL-N-(4-PICOLYL)-2-PHENYLACRYLAMIDE;N-ETHYL-N-(4-PICOLYL)ATROPAMIDE;N-ETHYL-N-(4-PYRIDYLMETHYL)-2-PHENYLACRYLAMIDE;Apotropicamide;N-Ethyl-α-methylene-N-[(pyridin-4-yl)methyl]benzeneacetamide;N-Ethyl-N-(4-picolyl)-2-phenylacrylamide N-Ethyl-N-(4-pyridylmethyl)-2-phenylacrylamide;TropicaMide Related CoMpound B;N-Ethyl-alpha-methylene-N-(4-pyridinylmethyl)benzeneacetamide
• CAS NO: 57322-50-6
• Molecular Formula: C₁₇H₁₈N₂O
• Molecular Weight: 266.34
• Mol File: 57322-50-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 492.042ºC at 760 mmHg
• Flash Point: 251.378ºC
• Appearance: /
• Density: 1.096g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: N-ETHYL-N-(4-PICOLYL)ATROPAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ETHYL-N-(4-PICOLYL)ATROPAMIDE(57322-50-6)
• EPA Substance Registry System: N-ETHYL-N-(4-PICOLYL)ATROPAMIDE(57322-50-6)

Safety Data

• Statements: 20/21/22
• Safety Statements: 13-36/37/39
• Hazardous Substances Data: 57322-50-6(Hazardous Substances Data)

Usage

Uses

N-Ethyl-N-(4-picolyl)atropamide is a major impurity of Tropicamide (T892650), a medication used to dilate the pupil.

InChI:InChI=1/C17H18N2O/c1-3-19(13-15-9-11-18-12-10-15)17(20)14(2)16-7-5-4-6-8-16/h4-12H,2-3,13H2,1H3

Upstream product

• 1508-75-4 tropicamide 
• 201230-82-2 carbon monoxide 
• 51246-20-9 1-phenyl-1-iodoethylene 
• 33403-97-3 4-(ETHYLAMINOMETHYL)PYRIDINE 

Relevant articles and documents

Synthesis of N-picolylcarboxamides via palladium-catalysed aminocarbonylation of iodobenzene and iodoalkenes

A systematic investigation of the palladium-catalysed aminocarbonylation of iodobenzene, 1-iodocyclohexene and 1′-iodostyrene in the presence of N-nucleophiles containing pyridyl moieties (2-, 3- and 4-picolylamine, N-ethyl-4-picolylamine, di-(2-picolyl)amine) was carried out. The two types of iodo substrates differ substantially regarding the selectivity towards carbonylation: while the aminocarbonylation of iodobenzene resulted in the formation of carboxamide and ketocarboxamide mixtures under various conditions, with the predominant formation of ketocarboxamide even at low carbon monoxide pressure, the aminocarbonylation of iodoalkenes under same conditions gave the corresponding unsaturated carboxamide exclusively. Most of the carboxamides and phenylglyoxylamides, obtained via single and double carbon monoxide insertion, respectively, were isolated in yields of synthetic interest (up to 86%). Low reaction rates and unexpected chemoselectivity towards carboxamide formation have been observed with di-(2-picolyl)amine as N-nucleophile in the aminocarbonylation of iodobenzene.