Indole is an organic chemical compound with CAS number 120-72-9 and formula C8H7N. It is also known under the names 2,3-benzopyrrole, ketole, and 1-benzazole.
The developing of indole chemistry began with the study of the dye indigo. Even the name of the compound is a portmanteau of two words “indigo” and “oleum”, because the chemical was first received due to the treatment of the indigo dye with oleum. The first person to propose its formula was German chemist Adolf von Baeyer.
The substance is an aromatic compound with a bicyclic structure that consists of a six-membered benzene ring joined with a five-membered pyrrole ring. The chemical can be produced by a variety of bacteria and is widely distributed in the nature. It regulates diverse aspects of bacterial physiology, like resistance to drugs, virulence, spore formation, etc.
Indole is a white solid with a strong fecal smell. However, at low concentrations the odor of the substance is pleasant, flowery. Besides, on exposure to light its white color turns red. The other indole properties include:
- Molecular weight: 117.15 g/mol;
- Density: 1.1747 g/cm3;
- Melting point: 52 to 54 °C;
- Boiling point: 253 to 254 °C.
The chemical is soluble in hot water, benzene, ether, toluene, fixed oils, insoluble in glycerol and mineral oils. It is air sensitive and incompatible with iron, iron salts, and strong oxidizing agents.
This organic should be handled with care since it is toxic in contact with skin and if swallowed. It is dangerous for the environment too, and can cause long-term adverse effects in the aquatic environment.
Synthesis and Uses
Synthesis of indole and its derivatives can be performed by number of various methods. The three most popular are:
- Vapor-phase reaction of aniline with ethylene glycol in the presence of catalyst.
- Leimgruber–Batcho synthesis reactions.
- Fischer synthesis process.
Indole uses include its application in various chemical reactions. Moreover, this chemical serves as a flavoring agent in food industry. It is a constituent of diverse flower scents and perfumes.
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