1-Naphthol

changed 477188585 alpha-Naphthol.svg Skeletal formula skin-invert 1-Naphthol-3D-balls.png bg-transparent Naphthalen-1-ol 1-Hydroxynaphthalene; 1-Naphthalenol; α-Naphthol 1817321 correct FDA 2A71EAQ389 correct kegg C11714 1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H KJCVRFUGPWSIIH-UHFFFAOYAZ correct EBI 122617 201-969-4 69192 correct chemspider 1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H correct chemspider KJCVRFUGPWSIIH-UHFFFAOYSA-N correct CAS 90-15-3 7005 Oc2cccc1ccccc12 correct chemspider correct EBI 10319 6739 10 8 1 Colorless or white solid 1.10 g/cm3 95 to 96 278 to 280 −98.2·10−6 cm3/mol 1-Naphthol https://pubchem.ncbi.nlm.nih.gov/compound/7005#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov en 05 06 07 09 Danger 302 311 312 315 317 318 335 410 412 261 262 264 264+265 270 271 272 273 280 301+317 302+352 304+340 305+354+338 316 317 319 321 330 332+317 333+317 361+364 362+364 391 403+233 405 501 2-Naphthol 1-Naphthol, or α-naphthol, is an organic compound with the formula C10H7OH. It is a fluorescent white solid. 1-Naphthol differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol. Both isomers are soluble in simple organic solvents. They are precursors to a variety of useful compounds. Production 1-Naphthol is prepared by two main routes. In one method, naphthalene is nitrated to give 1-nitronaphthalene, which is hydrogenated to the amine followed by hydrolysis: C10H8 + HNO3 -> C10H7NO2 + H2O C10H7NO2 + 3H2 -> C10H7NH2 + 2H2O C10H7NH2 + H2O -> C10H7OH + NH3 Alternatively, naphthalene is hydrogenated to tetralin, which is oxidized to 1-tetralone, which undergoes dehydrogenation. Reactions Some reactions of 1-naphthol are explicable with reference to its tautomerism, which produces a small amount of the keto tautomer.Gut Ivo Glynne Scheibler Lukas C. Wirz Jakob 2010-07-30 Flash photolytic generation of two keto tautomers of 1-naphthol in aqueous solution: kinetics and equilibria of enolization https://pubs.rsc.org/en/content/articlelanding/2010/pp/c0pp00034e Photochemical & Photobiological Sciences en 9 7 901–907 10.1039/C0PP00034E 1474-9092 subscription frameless|left|384px One consequence of this tautomerism is the Bucherer reaction: the ammonolysis of 1-naphthol to give 1-aminonaphthalene. Low temperature sulfonation of 1-naphthol gives 1-hydroxynaphthalene-2-sulfonic acid. 1-Naphthol biodegrades via formation of 1-naphthol-3,4-oxide, which converts to 1,4-naphthoquinone.Annual Review of Pharmacology and Toxicology 2011 The Chemical Biology of Naphthoquinones and Its Environmental Implications Yoshito Kumagai Yasuhiro Shinkai Takashi Miura Arthur K. Cho Arthur K. Cho 52 10.1146/annurev-pharmtox-010611-134517 21942631 221–47 The 4-position of 1-naphthol is susceptible to electrophilic attack. This regioselective reaction is exploited in the preparation of diazo dyes, which are form using diazonium salts. Reduction of the diazo derivatives gives 4-amino-1-naphthol.10.15227/orgsyn.003.0007 free 1,4-Aminonaphthol Hydrochloride J. B. Conant R. E. Lutz B. B. Corson Organic Syntheses 1923 3 7 10.15227/orgsyn.017.0009 free 1,2-Aminonaphthol Hydrochloride Organic Syntheses 1937 17 9 Louis F. Fieser Partial reduction of 1-naphthol gives the tetrahydro derivative, leaving intact the phenol ring.10.15227/orgsyn.037.0080 free Ar-Tetrahydro-a-Naphthol Organic Syntheses 1957 37 80 C. David Gutsche Hugo H. Peter Full hydrogenation is catalyzed by rhodium.10.15227/orgsyn.051.0103 free Hydrogenation of Aromatic Nuclei: 1-Decalol Organic Syntheses 1971 51 103 A. I. Meyers W. N. Beverung R. Gault Applications and occurrence 1-Naphthol is a precursor to a variety of insecticides including carbaryl and pharmaceuticals including nadololM.E. Condon et al Journal of Medicinal Chemistry Nondepressant β-adrenergic blocking agents. 1. Substituted 3-amino-1-(5,6,7,8-tetrahydro-1-naphthoxy)-2-propanols 21 9 913–922 1978 German 10.1021/jm00207a014 31485 DE 2258995 2,3-cis-1,2,3,4-Tetrahydro-5[2-hydroxy-3-(tert.-butylamino)-propoxy]-2,3-naphthalindiol 1973-06-07 1972-12-01 F.R. Hauck, C.M. Cimarusti, V.L. Narayan E.R. Squibb & Sons, Inc. as well as for the antidepressant sertralineK. Vukics T. Fodor J. Fischer I. Fellevári S. Lévai Org. Process Res. Dev. Improved industrial synthesis of antidepressant Sertraline 6 1 82–85 2002 German 10.1021/op0100549 and the anti-protozoan therapeutic atovaquone.B.N. Roy G.P. Singh P.S. Lathi M.K. Agarwal Indian J. Chem. A novel process for synthesis of Atovaquone 52B 1299–1312 2013 German https://web.archive.org/web/20220530185938/http://nopr.niscair.res.in/bitstream/123456789/21838/1/IJCB%2052B(10)%201299-1312.pdf dmy-all 2022-05-30 http://nopr.niscair.res.in/bitstream/123456789/21838/1/IJCB%2052B%2810%29%201299-1312.pdf It undergoes azo coupling to give various azo dyes, but these are generally less useful than those derived from 2-naphthol.Gerald Booth Naphthalene Derivatives 2005 10.1002/14356007.a17_009. full-text PDFC. Kaiser T. Jen E. Garvey W.D. Bowen D.F. Colella J.R. Wardell Jr. Journal of Medicinal Chemistry Adrenergic agents. 4. Substituted phenoxypropanolamine derivatives as potential β-adrenergic agonists 20 5 687–689 1977 German 10.1021/jm00215a014 16136 1-Naphthol is a metabolite of the insecticide carbaryl and naphthalene. Along with TCPy, it has been shown to decrease testosterone levels in adult men. Epidemiology 17 1 61–68 Exposure to Nonpersistent Insecticides and Male Reproductive Hormones Meeker, John D. Ryan, Louise Barr, Dana B. Hauser, Russ 10.1097/01.ede.0000190602.14691.70 16357596 January 2006 24829926 free Other uses 1-Naphthol is used in each of the following chemical tests, which predate the use of spectroscopic and chromatographic methods: Molisch's test gives a red- or purple-colored compound to indicate the presence of carbohydrate. rapid furfural test turns purple quickly (<30s) if fructose is present, distinguishing it from glucose. Sakaguchi test turns red to indicate the presence of arginine in proteins. Voges–Proskauer test changes color from yellow to red to indicate that glucose is being broken down into acetoin which is used by bacteria for external energy storage. 1-Naphthol exhibits some non-peptizing properties, making it ideal as: An oxidation inhibitor for industrial soaps, especially as a specified antioxidant in napalm and others fuel thickeners. An catalyst in the saponification of fatty esters. Safety 1-Naphthol has been described as "moderately toxic". References External links NIST Chemistry WebBook 1-Naphthalenol Naphthols 19 168–169 1 Category:1-Naphthyl compounds