This is. The first azo dye was aniline yellow. The diamines are condensed with phosgene to give methylene diphenyl diisocyanate, a precursor to urethane polymers. Below are some classes of its reactions. The principal use of aniline in the dye industry is as a precursor to indigo, the blue of blue jeans.[6]. Salvarsan's targeted microorganism, not yet recognized as a bacterium, was still thought to be a parasite, and medical bacteriologists, believing that bacteria were not susceptible to the chemotherapeutic approach, overlooked Alexander Fleming's report in 1928 on the effects of penicillin. Soon thereafter, applying a method reported in 1854 by Antoine Béchamp,[25] it was prepared "by the ton". Its high reactivity reflects that it is an enamine, which enhances the electron-donating ability of the ring. Gerhard Domagk identified as an antibacterial a red azo dye, introduced in 1935 as the first antibacterial drug, prontosil, soon found at Pasteur Institute to be a prodrug degraded in vivo into sulfanilamide – a colorless intermediate for many, highly colorfast azo dyes – already with an expired patent, synthesized in 1908 in Vienna by the researcher Paul Gelmo for his doctoral research. 3. ", http://www.nuclear-weapons.info/cde.htm#Corporal, CDC - NIOSH Pocket Guide to Chemical Hazrds, https://en.wikipedia.org/w/index.php?title=Aniline&oldid=989741451, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Chemical articles with multiple CAS registry numbers, Chemical articles with multiple PubChem CIDs, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Articles with unsourced statements from May 2010, Wikipedia articles incorporating a citation from the 1911 Encyclopaedia Britannica with Wikisource reference, Wikipedia articles incorporating text from the 1911 Encyclopædia Britannica, Inconsistent wikidata for Commons category, Wikipedia articles incorporating a citation from EB9, Creative Commons Attribution-ShareAlike License, J. Fritzsche (1840) "Ueber das Anilin, ein neues Zersetzungsproduct des Indigo,", This page was last edited on 20 November 2020, at 19:36. [28] 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 medicine – failed and switched to modifying Béchamp's atoxyl, the first organic arsenical drug, and serendipitously obtained a treatment for syphilis – salvarsan – the first successful chemotherapy agent. In this test, pink colour of KMnO 4 disappears, when alkaline KMnO 4 is added to an unsaturated hydrocarbon. [35], Many methods exist for the detection of aniline. [31], In the 1940s and early 1950s, aniline was used with nitric acid or dinitrogen tetroxide as rocket fuel for small missiles and the Aerobee rocket. The combination is hypergolic, igniting on contact between fuel and oxidizer. Hypochlorous acid gives 4-aminophenol and para-amino diphenylamine. [26] The Béchamp reduction enabled the evolution of a massive dye industry in Germany. Like other amines, aniline is a base (pKaH = 4.6) and nucleophile, although it is a weaker base and poorer nucleophile than structurally similar aliphatic amines. These polymers exhibit rich redox and acid-base properties. For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, H2NC6H4SO3H. At the time of mauveine's discovery, aniline was expensive. Aniline is an organic compound with the formula C 6 H 5 NH 2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. Sanjeeva Kumar, Special Secretary, Ministry of Health, was quoted by ANI, a news wire agency, as saying this. In the parent aniline, the lone pair is approximately 12% s character, corresponding to sp7.3 hybridization. [6], In commerce, three brands of aniline are distinguished: aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and para-toluidines; and aniline oil for safranine, which contains aniline and ortho-toluidine and is obtained from the distillate (échappés) of the fuchsine fusion. The chemistry of aniline is rich because the compound has been cheaply available for many years. N-Methylation of aniline with methanol at elevated temperatures over acid catalysts gives N-methylaniline and dimethylaniline: N-Methylaniline and dimethylaniline are colorless liquids with boiling points of 193–195 °C and 192 °C, respectively. Physical state: 2. G. M. Wójcik "Structural Chemistry of Anilines" in Anilines (Patai's Chemistry of Functional Groups), S. Patai, Ed. Iron (II) Hydroxide Test for Nitro Groups. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide. Aniline is, for example, more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution. [29], In 1932, Bayer sought medical applications of its dyes. Aniline is a slightly pyramidalized molecule, with hybridization of the nitrogen somewhere between sp3 and sp2. [18] As additives to rubber, aniline derivatives such as phenylenediamines and diphenylamine, are antioxidants. First, benzene is nitrated with a concentrated mixture of nitric acid and sulfuric acid at 50 to 60 °C to yield nitrobenzene. Like phenols, aniline derivatives are highly susceptible to electrophilic substitution reactions. Being a standard reagent in laboratories, aniline is used for many niche reactions.