4-aniline

4-(tris(4-methyl-1H -pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy,...

Full description

Saved in:
Bibliographic Details
Published in:MolBank 2024-06, Vol.2024 (2)
Main Authors: Garrison, Bradley B, Duhamel, Joseph E, Antoine, Nehemiah, Symes, Steven J. K, Grice, Kyle A, McMillen, Colin D, Pienkos, Jared A
Format: Article
Language:English
Subjects:
Analysis
Aniline
Chemical synthesis
Density functionals
Identification and classification
Infrared spectroscopy
Mass spectrometry
Methods
Methyl groups
Nuclear magnetic resonance spectroscopy
Pyrazoles
Structure
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:4-(tris(4-methyl-1H -pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and single-crystal analysis. An analysis of crystals grown from the layering method (CH[sub.2] Cl[sub.2] /acetone/pentane) indicated two distinct polymorphs of the title compound. Moreover, density functional theory calculations utilizing the MN15L density functional and the def2-TZVP basis set indicated that 4-(tris(4-methyl-1H -pyrazol-1-yl)methyl)aniline forms with similar energetics to the previously reported unmethylated analog.
ISSN:1422-8599
1422-8599
DOI:10.3390/M1823