Indigofera tinctoria, also called true indigo, is a species of plant from the bean family that was one of the original sources of indigo dye.
Indigofera tinctoria, also called true indigo, is a species of plant from the bean family that was one of the original sources of indigo dye.
Indigo dye is an organic compound with a distinctive blue color. Indigo is a natural dye obtained from the leaves of some plants of the Indigofera genus, in particular Indigofera tinctoria. Dye-bearing Indigofera plants were once common throughout the world. It is now produced via chemical routes from aniline. Blue colorants are rare. Since indigo is insoluble, it is also referred to as a pigment (C.I. Pigment Blue 66, C.I.).
Most indigo dye produced today is synthetic, constituting around 80,000 tonnes each year, as of 2023. It is most commonly associated with the production of denim cloth and blue jeans, where its properties allow for effects such as stone washing and acid washing to be applied quickly.
Aniline (From Portuguese: anil, meaning 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formula C6H5NH2. Consisting of a phenyl group (−C6H5) attached to an amino group (−NH2), aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
Relative to benzene, aniline is "electron-rich". It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone to oxidation: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the formation of strongly colored, oxidized impurities. Aniline can be diazotized to give a diazonium salt, which can then undergo various nucleophilic substitution reactions.