Mauveine

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Mauveine, also known as aniline purple, was the first synthetic organic dye. It was discovered serendipitously in 1856 by an 18-year old William Perkin, who was trying to synthesize the anti-malaria drug quinine as a challenge offered by his professor, August Wilhelm von Hofmann. In one of his attempts to make quinine, Perkin oxidized aniline using chromic acid. Under these conditions, the aniline reacted with toluidine impurities in it to produce a black solid, a fairly common result in "failed" organic syntheses. However, while trying to clean out his flask, Perkin discovered that some component of the black solid dissolved in alcohol to give a purple-colored solution, which proved to be an effective dye for silk and other textiles.

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Perkin patented the new dye and the next year, he opened a dyeworks in London to mass produce it. Mauve became highly fashionable—in 1862, Queen Victoria appeared at the Royal Exhibition in a mauve silk gown. Mauve fell out of fashion in the late 1860s to newer synthetic colors, but not before making Perkin's fortune and birthing the synthetic chemical industry. Later work on chemical dyes also lead to the (accidental) development of modern chemotherapy (see Sulfonamide).

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Incidentally, the actual molecular structure of mauveine proved quite difficult to determine and was not known with certainty until 1994. It is actually a mixture of two related compounds, mauveine A, shown above at right, and mauveine B, which has one additional methyl group.

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