Aniline Germany. Today, the name of BASF, originally "Badische Anilin- und Soda-Fabrik" (English: Baden Aniline and Soda Factory), now the largest chemical supplier, echoes the legacy of the synthetic dye industry, built via aniline dyes and extended via the related azo dyes. The first azo dye was aniline yellow. In the late 19th century, aniline emerged as an analgesic drug, its cardiac-suppressive side effects countered with caffeine. During the first decade of the 20th century, while trying to modify synthetic dyes to treat African sleeping sickness, Paul Ehrlich – who had coined the term "chemotherapy" for his "magic bullet" approach to
Aniline on the nitrogen is partially delocalized into the pi system of the benzene ring. Missing in such analysis is consideration of solvation. Aniline is, for example, more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution. Aniline reacts with acyl chlorides such as acetyl chloride to give amides. The amides formed from aniline are sometimes called anilides, for example CH-CO-NH-CH is acetanilide. At high temperatures aniline and carboxylic acids react to give the anilides. "N"-Methylation of aniline with methanol at elevated temperatures over acid catalysts gives "N"-methylaniline and dimethylaniline: "N"-Methylaniline and dimethylaniline are