Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Aniline (from Portuguese anil 'indigo shrub', and -ine indicating a derived substance)[6] 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.[7] It is toxic to humans.
Relative to benzene, it 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.
Like other amines, aniline is both a base (pKaH = 4.6) and a nucleophile, although less so than structurally similar aliphatic amines.
Because an early source of the benzene from which they are derived was coal tar, aniline dyes are also called coal tar dyes.
^Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 416, 668. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. Aniline, for C6H5-NH2, is the only name for a primary amine retained as a preferred IUPAC name for which full substitution is permitted on the ring and the nitrogen atom. It is a Type 2a retained name; for the rules of substitution see P-15.1.8.2. Substitution is limited to substituent groups cited as prefixes in accordance with the seniority of functional groups explicitly expressed or implied in the functional parent compound name. The name benzenamine may be used in general nomenclature.
^ abcdeNIOSH Pocket Guide to Chemical Hazards. "#0033". National Institute for Occupational Safety and Health (NIOSH).
^Vollhardt, P.; Schore, Neil (2018). Organic Chemistry (8th ed.). W. H. Freeman. p. 1031. ISBN 9781319079451.
^ abc"Aniline". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^"Aniline". cameochemicals.noaa.gov. US NOAA Office of Response and Restoration. Retrieved 2016-06-16.
^"aniline | Etymology, origin and meaning of aniline by etymonline". www.etymonline.com. Retrieved 2022-02-15.
^Cite error: The named reference Ullmann was invoked but never defined (see the help page).
Aniline (from Portuguese anil 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formula C6H5NH2. Consisting of...
The aniline point of an oil is defined as the minimum temperature at which equal volumes of aniline (C 6H 5NH 2) and lubricant oil are miscible, i.e....
Aniline leather is a type of leather dyed exclusively with soluble dyes. The dye colours the leather without producing the uniform surface of a topcoat...
Aniline Yellow is a yellow azo dye and an aromatic amine. It is a derivative of azobenzene. It has the appearance of an orange powder. Aniline Yellow was...
Mauveine, also known as aniline purple and Perkin's mauve, was one of the first synthetic dyes. It was discovered serendipitously by William Henry Perkin...
anilinium, which is the conjugate acid of aniline, C6H5NH2. Anilinium chloride is produced by treatment of aniline with hydrochloric acid. The cation consists...
of its original name Badische Anilin- und Sodafabrik (German for 'Baden Aniline and Soda Factory'), is a European multinational company and the largest...
Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine...
model, the former being closer to rose. Magenta took its name from an aniline dye made and patented in 1859 by the French chemist François-Emmanuel Verguin...
oxidation of aniline, which had been isolated only 20 years previously. He developed the first commercially successful route to the dye called Aniline black...
Antifebrin. Acetanilide can be produced by reacting acetic anhydride with aniline: C6H5NH2 + (CH3CO)2O → C6H5NHCOCH3 + CH3COOH The preparation used to be...
N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a...
Aniline Blue WS, also called aniline blue, diphenylamine blue, China blue, or Soluble blue, is a mixture of methyl blue and water blue. It may also be...
Chemical Company (est. 1858), General Chemical Company (est. 1899), National Aniline & Chemical Company (est. 1917), Semet-Solvay Company (est. 1895), and the...
April 1929 and headquartered in New York City. It had stakes in General Aniline Works (GAW), Agfa-Ansco Corporation, and Winthrop Chemical Company, among...
stronger acids. Steric Inhibition of Protonation caused by substitution of anilines to become weaker bases, compared to substitution of isomers in the meta...
malaria. He noticed an unexpected residue, which turned out to be the first aniline dye. Perkin originally named the dye Tyrian purple after the historical...
organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless...
process for reducing nitrobenzene to aniline in 1854, known as the Bechamp Process, making the production of aniline easy. Widespread isolation of phenol...
volumes of aniline and the base stock are soluble High aniline points (approximately 100°C or greater) imply a paraffinic base stock, while low aniline points...
Methylaniline may refer to: N-Methylaniline Toluidines 2-Methylaniline (o-toluidine) 3-Methylaniline (m-toluidine) 4-Methylaniline (p-toluidine) This set...
in organic chemistry. Sulfanilic acid can be produced by sulfonation of aniline with concentrated sulfuric acid. This proceeds via phenylsulfamic acid;...
The Clayton Aniline Company Ltd. was a British manufacturer of dyestuffs, founded in 1876 by Charles Dreyfus in Clayton, Manchester. Charles Dreyfus was...
derivatives of aniline (H2N−C6H5). Aniline reacts with acyl chlorides or carboxylic anhydrides to give anilides. For example, reaction of aniline with acetyl...
nitrobenzene industrially produced is hydrogenated to aniline: C6H5NO2 + 3 H2 → C6H5NH2 + 2 H2O Aniline is a precursor to urethane polymers, rubber chemicals...
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