181059-76-7

Basic information

• Product Name: Benzenamine, 2-(2,2,3,3,4,4,4-heptafluoro-1,1-diphenylbutyl)-
• CAS NO: 181059-76-7
• Molecular Formula: C22H16F7N
• Molecular Weight: 427.365
• Mol File: 181059-76-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenamine, 2-(2,2,3,3,4,4,4-heptafluoro-1,1-diphenylbutyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 2-(2,2,3,3,4,4,4-heptafluoro-1,1-diphenylbutyl)-(181059-76-7)
• EPA Substance Registry System: Benzenamine, 2-(2,2,3,3,4,4,4-heptafluoro-1,1-diphenylbutyl)-(181059-76-7)

Safety Data

• Hazardous Substances Data: 181059-76-7(Hazardous Substances Data)

Upstream product

• 106877-28-5 2-(Nonafluorobutyl)aniline 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 615-43-0 2-iodophenylamine 

Relevant articles and documents

Synthesis of 9-(Cn-1F2n-1)-substituted acridine by the reaction of 2-(CnF2n+1)-substituted aniline with orthomethyl-substituted aromatic Grignard reagent

Treatment of 2-(perfluoroalkyl)aniline with 2-tolylmagnesium bromide or chloride or their substituted analogs yields an acridine containing a shorter perfluoroalkyl group at the 9 position and devoid of the methyl group of the Grignard substrate. Interestingly, no acridine is produced in an attempted reaction with aryl magnesium bromide without the ortho methyl group. With 2-fluoro-6-methylphenylmagnesium bromide the methyl group is eliminated and the fluorine is retained in the acridine product. Results of the mechanistic studies strongly suggest that loss of the methyl group occurs as methanol during air oxidation and hydrolysis of the intermediate products during aqueous workup.

Base-mediated reactions of ortho- and para-perfluoroalkylanilines

The title chemistry involves regioselectively a benzylic position of the perfluoroalkyl group and provides an easy access to substituted quinolines and methanes.