2-Aminophenol

changed 477212496 o-Aminophenol.svg 140px skin-invert 2-aminophenol-space-filling.png 100px Space filling model of 2-aminophenol bg-transparent 2-aminophenol-ball-and-stick.png 100px Ball-and-stick model of 2-aminophenol bg-transparent 2-Aminophenol Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 690 10.1039/9781849733069-FP001 978-0-85404-182-4 o-Aminophenolortho-Aminophenol2-Hydroxyaniline2-Amino-1-hydroxybenzene correct EBI 18112 correct FDA 23RH73DZ65 correct drugbank DB01726 Oc1ccccc1N correct chemspider 5596 correct kegg C01987 CDAWCLOXVUBKRW-UHFFFAOYAP correct EBI 28319 correct chemspider 1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2 correct chemspider CDAWCLOXVUBKRW-UHFFFAOYSA-N correct CAS 95-55-6 5801 202-431-1 SJ4950000 2512 1/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2 6 7 1 1 White orthorhombic pyramidal needles 1.328 g/cm3 slightly soluble in cold water, soluble in hot water 174 4.78 (amino; 20 °C, H2O) 9.97 (phenol; 20 °C, H2O) Haynes, William M. 2016 CRC Handbook of Chemistry and Physics 97th CRC Press 978-1498754286 5–89 CRC Handbook of Chemistry and Physics 07 08 Warning 302 332 341 201 202 261 264 270 271 281 301+312 304+312 304+340 308+313 312 330 405 501 2-Aminophenol is an organic compound with the formula C6H7NO 1. Along with its isomer 4-aminophenol, it is an amphoteric molecule and a reducing agent. It is a useful reagent for the synthesis of dyes and heterocyclic compounds. Mitchell Stephen C. Waring Rosemary H. Ullmann's Encyclopedia of Industrial Chemistry Aminophenols 2000 10.1002/14356007.a02_099 978-3-527-30385-4 . Reflecting its slight hydrophilic character, white powder is moderately soluble in alcohols and can be recrystallized from hot water. Synthesis and structure 2-Aminophenol (and its isomer, 4-aminophenol) is industrially synthesized by reducing the corresponding nitrophenol by hydrogen in the presence of various catalysts. The nitrophenols can also be reduced with iron. The compound exhibits intra- and intermolecular hydrogen bonding involving the neighbouring amine and hydroxyl groups. As a result, 2-aminophenol has a relatively high melting point (174 °C) compared to other compounds with a similar molecular mass; for example, 2-methylphenol melts at 31 °C. Reference Handbook of Fine Chemicals Acros Organics Publishers, Fisher Scientific UK 2007 http://www.acros.com Applications 2-Aminophenol has a variety of uses. As a reducing agent, it is marketed under the names of Atomal and Ortol to develop black-and-white photographs. 2-Aminophenol is an intermediate in the synthesis of dyes. It is particularly useful in yielding metal-complex dyes when diazotized and coupled to a phenol, naphthol, or other aromatic or resonant dye species. Metal complex dyes using copper or chromium are commonly used for producing dull colors. Tridentate ligand dyes are useful because they are more stable than their bi- or mono-dentate counterparts. Grychtol Klaus Mennicke Winfried Ullmann's Encyclopedia of Industrial Chemistry Metal-Complex Dyes 2000 10.1002/14356007.a16_299 978-3-527-30385-4 Hunger Klaus Mischke Peter Rieper Wolfgang Raue Roderich Kunde Klaus Engel Aloys Ullmann's Encyclopedia of Industrial Chemistry Azo Dyes 2000 10.1002/14356007.a03_245 3-527-30673-0 500px 350px Due to the adjacency of the amino and hydroxyl groups, 2-aminophenol readily forms heterocycles. These heterocycles, such as benzoxazoles, can be biologically active and useful in the pharmaceutical industry: 375px 2-Aminophenol has application in the synthesis of ARN2966, paraxazone, leiopyrrole, Buu-Hoï N P. Rips Richard Cavier R. A New Class of Antispasmodies with Considerable Activity Journal of Medicinal and Pharmaceutical Chemistry 1959 1 23–30 10.1021/jm50002a002 13655026 arsphenamine, Christiansen Walter G. HYPOPHOSPHOROUS ACID PREPARATION OF ARSPHENAMINE. (3,31-DIAMINO-4,41-DIHYDROXY-ARSENO-BENZENE DIHYDROCHLORIDE.)1 Journal of the American Chemical Society 1920 42 11 2402–2405 10.1021/ja01456a042 1920JAChS..42.2402C and amoxapine. The reaction of 2-aminophenol with glycerol leads to 8-hydroxyquinoline. This chemical has some important uses. References Category:Aminophenols Category:2-Aminophenyl compounds Category:2-Hydroxyphenyl compounds