[23] In 1843, August Wilhelm von Hofmann showed that these were all the same substance, known thereafter as phenylamine or aniline. [24], In 1856, while trying to synthesise quinine, von Hofmann's student William Henry Perkin discovered mauveine and went into industry producing the first commercial synthetic dye.
Aniline is a slightly pyramidalized molecule, with hybridization of the nitrogen somewhere between sp3 and sp2.
Its high reactivity reflects that it is an enamine, which enhances the electron-donating ability of the ring. The reduction of nitrobenzene to aniline was first performed by Nikolay Zinin in 1842, using inorganic sulfide as a reductant (Zinin reaction). The amino group in aniline is flatter (i.e., it is a "shallower pyramid") than that in an aliphatic amine, owing to conjugation of the lone pair with the aryl substituent. Bis(2-acetoxyethyl)phenylammonium acetate, o-(Methoxycarboxy)phenylammonium hydrogen sulphate, 2-Methoxy-4-nitro-5-(sulphooxy)phenylammonium hydrogen sulphate, (4-Methoxyphenyl)(oxo)phenylammonium perchlorate. Aniline was later replaced by hydrazine. The C−N distance is also correspondingly shorter. PubChem CID 8870 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. [30] In 1939, at Oxford University, seeking an alternative to sulfa drugs, Howard Florey developed Fleming's penicillin into the first systemic antibiotic drug, penicillin G. (Gramicidin, developed by René Dubos at Rockefeller Institute in 1939, was the first antibiotic, yet its toxicity restricted it to topical use.) It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. [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. Aniline was first isolated in 1826 by Otto Unverdorben by destructive distillation of indigo. At the time of mauveine's discovery, aniline was expensive.
Illustrative of the drugs prepared from aniline is paracetamol (acetaminophen, Tylenol).
In the parent aniline, the lone pair is approximately 12% s character, corresponding to sp7.3 hybridization. "Phenylammonium Compounds" is a descriptor in the National Library of Medicine's controlled vocabulary thesaurus, MeSH (Medical Subject Headings).Descriptors are arranged in a hierarchical structure, which enables searching at various levels of specificity. Other aniline dyes followed, such as fuchsin, safranin, and induline. InChI: InChI=1/C6H7N.ClH/c7-6-4-2-1-3-5-6;/h1-5H,7H2;1H, InChIKey: InChIKey=MMCPOSDMTGQNKG-UHFFFAOYAJ After World War II, Cornelius P. Rhoads introduced the chemotherapeutic approach to cancer treatment. The largest scale industrial reaction of aniline involves its alkylation with formaldehyde. The two fuel components are hypergolic, producing a violent reaction on contact. Below are some classes of its reactions. The reaction of converting primary aromatic amine into diazonium salt is called diazotisation.
Aromatic amines such as aniline are, in general, much weaker bases than aliphatic amines. The early manufacture of aniline resulted in increased incidents of bladder cancer, but these effects are now attributed to naphthylamines, not anilines. Aniline can be diazotized to give a diazonium salt, which can then undergo various nucleophilic substitution reactions. Potassium permanganate in neutral solution oxidizes it to nitrobenzene; in alkaline solution to azobenzene, ammonia, and oxalic acid; in acid solution to aniline black. For example, this approach is used to convert toluene into toluidines and chlorobenzene into 4-chloroaniline. Aniline reacts with strong acids to form the anilinium (or phenylammonium) ion (C6H5-NH3+).[15]. [6], Other uses include rubber processing chemicals (9%), herbicides (2%), and dyes and pigments (2%). [16], Aniline reacts with acyl chlorides such as acetyl chloride to give amides. Today, the name of BASF, originally Badische Anilin- und Soda-Fabrik (English: Baden Aniline and Soda Factory), now the largest chemical supplier, echoes the legacy of the synthetic dye industry, built via aniline dyes and extended via the related azo dyes. He named it kyanol or cyanol. DTXSID00954877.
[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 reduction of nitrobenzene to aniline was also performed as part of reductions by Antoine Béchamp in 1854, using iron as the reductant (Bechamp reduction). Service Tel: +86-571-87759741, Marketing Tel: +86-571-89739798 skype, Copyright©2010-2020 Guidechem 浙B2-20090288-37. In aniline, the C−N bond length is 1.41 Å,[9] compared to 1.47 Å for cyclohexylamine,[10] indicating that there is partial π-bonding between N and C.[11], Industrial aniline production involves two steps. [7], Consistent with these factors, substituted anilines with electron donating groups are more pyramidalized, while those with electron withdrawing groups are more planar.
[29] Medications in high demand during World War II (1939–45), these first miracle drugs, chemotherapy of wide effectiveness, propelled the American pharmaceutics industry. It is used to stain neural RNA blue in the Nissl stain. Phenylammonium Chloride Safety data sheet According to 1907/2006/EC (REACH), 2015/830/EU SECTION 1: IDENTIFICATION OF THE SUBSTANCE/MIXTURE AND OF THE COMPANY/UNDERTAKING 1.1 Product identifier:Anilinium chloride CAS: 142-04-1 EC: 205-519-8 Index: 612-009-00-2 REACH: Non-applicable Formula: C₆H₅NH₂.HCl Molecular weight: 129.59 1.2 Relevant identified uses of the … In 1834, Friedlieb Runge isolated a substance from coal tar that turned a beautiful blue color when treated with chloride of lime. Its acetate is used in the aniline acetate test for carbohydrates, identifying pentoses by conversion to furfural. 2007, Wiley-VCH, Weinheim. Aniline combines directly with alkyl iodides to form secondary and tertiary amines. [35], Many methods exist for the detection of aniline. Aniline chloride ANILINE HYDROCHLORIDE aniline hydrochloride Anilinium chloride Benzenamine, hydrochloride CCRIS 45 Chlorid anilinu [Czech] Phenylamine hydrochloride Phenylammonium chloride Sul anilinova [Czech] ''aniline Salt'' Registries: PubChem CID 8870 PubChem ID 152022 [33][34] The IARC lists it in Group 3 (not classifiable as to its carcinogenicity to humans) due to the limited and contradictory data available. [8] (For comparison, in more strongly pyramidal methylamine, this value is ~125°, while a planar nitrogen like that of formamide has an angle of 180°.) [13], Boiled with carbon disulfide, it gives sulfocarbanilide (diphenylthiourea) (CS(NHC6H5)2), which may be decomposed into phenyl isothiocyanate (C6H5CNS), and triphenyl guanidine (C6H5N=C(NHC6H5)2).[13]. ), The pyramidalization angle between the C–N bond and the bisector of the H–N–H angle is 142.5°. It is also dense, and can be stored for extended periods. (m3/ug)): Mackay model : 0.000625 Octanol/air (Koa) model: 0.00191 Fraction sorbed to airborne particulates (phi): Junge-Pankow model : 0.0221 Mackay model : 0.0476 Octanol/air (Koa) model: 0.133 Atmospheric Oxidation (25 deg C) [AopWin v1.92]: Hydroxyl Radicals Reaction: OVERALL OH Rate Constant = 16.6779 E-12 cm3/molecule-sec Half-Life = 0.641 Days (12-hr day; 1.5E6 OH/cm3) Half-Life … An idealized equation is shown: The resulting diamine is the precursor to 4,4'-MDI and related diisocyanates. [14]. Likewise, it is also prone to oxidation: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening of the sample (to yellow or red) due to the formation of strongly colored, oxidized impurities.
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