A new class of N-aryl amino alcohols were designed, synthesized and evaluated as asphaltene aggregation inhibitors–dispersants. Structures of all compounds were corroborated by FTIR, ¹H, ¹³C, ¹¹B NMR and Mass Spectroscopy. The boronic acid moiety was included into the structure of the amino-alcohols because it presents low acidic Brönsted character but a good effectiveness as Lewis acid, feature which is assumed important in the interaction with asphaltenes. Boron based compounds are believed to form tetrameric complexes due to spectrometric evidence, in addition, they showed good efficiencies as asphaltene aggregation inhibitors, which was confirmed by flocculation–precipitation kinetics and rheological behavior experiments. Molecular modeling was used to analyze the aggregation mechanisms among asphaltenes and the interactions between them and amino-alcohols. Because of an outstanding agreement between theoretical and experimental results, a mechanism of interaction between the chemical compounds and asphaltenes is proposed.