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| | 1-Naphthol Basic information |
| | 1-Naphthol Chemical Properties |
| Melting point | 94-96 °C(lit.) | | Boiling point | 278-280 °C(lit.) | | density | 1.224 | | vapor density | 4.5 (120 °C, vs air) | | vapor pressure | 1 mm Hg ( 94 °C) | | refractive index | 1.6224 | | Fp | 125 °C | | storage temp. | Store below +30°C. | | solubility | Soluble in benzene, chloroform, ether and ethanol. | | form | Crystalline Flakes | | pka | 9.34(at 25℃) | | color | white to off-white | | Odor | Slight phenolic odor | | explosive limit | 5% | | Water Solubility | 436.7mg/L(25 ºC) | | λmax | 324nm(MeOH)(lit.) | | Sensitive | Air & Light Sensitive | | Merck | 14,6383 | | BRN | 1817321 | | Stability: | Stable, but air and light sensitive - store under inert gas. Incompatible with strong bases, strong oxidizing agents. | | InChIKey | KJCVRFUGPWSIIH-UHFFFAOYSA-N | | LogP | 2.84 at 25℃ | | CAS DataBase Reference | 90-15-3(CAS DataBase Reference) | | NIST Chemistry Reference | 1-Naphthalenol(90-15-3) | | EPA Substance Registry System | 1-Naphthol (90-15-3) |
| | 1-Naphthol Usage And Synthesis |
| Description | 1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.
α-naphtol, combined with epichlorhydrine and sodium hydroxide to form alpha-naphtyl glycidyl ether, caused sensitization in one of three workers in a chemical plant. | | Chemical Properties | Pale grey to brown solid with an unpleasant phenol odour. Darkens in the presence of light. Evaporates with water vapour. Soluble in ethanol, ether, benzene, chloroform and alkali solutions, insoluble in water. Precipitates violet when exposed to ferric chloride. | | Uses | 1-Naphthol is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol. It is used as biomarkers. It is used in analytical chemistry as Molisch's reagent (1-naphthol dissolved in ethanol) for checking the presence of carbohydrates. It plays an essential role with sodium hypobromite to detect the presence of arginine in proteins, which is called as Sakaguchi test. | | Preparation | 2-Isopropylnaphthalene can be used to synthesize 1-naphthol by oxidation via the hydroperoxide (Hock synthesis).
Historically 1-naphthol was produced via caustic fusion of naphthalene-1-sulfonic acid, but this was superseded by the I.G. Farbenindustrie process involving hydrolysis of 1-naphthylamine with aqueous 22 % sulfuric acid at 200°C under pressure in a lead-lined autoclave. To obtain a purer product, Union Carbide developed a process based on catalytic oxidation of tetralin to 1-tetralol and 1-tetralone followed by dehydrogenation. The two-stage catalytic process is claimed to give an overall yield of 72% 1-naphthol, with an overall efficiency of 97%. | | Definition | ChEBI: 1-naphthol is a naphthol carrying a hydroxy group at position 1. It has a role as a genotoxin and a human xenobiotic metabolite. | | Application | 1-Naphthol is a hydroxyl-aromatic compound. It has been used as a prooxidant to analyze its ability to induce hemolysis in a zebrafish G6PD (glucose-6-phosphate dehydrogenase) deficiency model. | | Synthesis Reference(s) | Synthetic Communications, 21, p. 379, 1991 DOI: 10.1080/00397919108016759
Journal of the American Chemical Society, 107, p. 493, 1985 DOI: 10.1021/ja00288a037 | | General Description | 1-Naphthol, a metabolite of carbaryl and naphthanlene. It is formed by spontaneous reaction from (1R, 2S)-Naphthalene epoxide followed to form 1, 4-Dihydroxynaphthalene. | | Hazard | Toxic by ingestion and skin absorption. | | Flammability and Explosibility | Notclassified | | Contact allergens | 1-Naphthol can be used in dye manufacture and is
classified as a hair dye. Combined with epichlorhydrin
and NaOH to form alpha-naphthyl glycidyl ether, it caused
sensitization in one of three workers in a chemical plant. | | Safety Profile | Poison by ingestion and
intraperitoneal routes. Moderately toxic by
skin contact. An experimental teratogen.
Experimental reproductive effects. A severe
eye and skin irritant. Mutation data reported.
Ingestion of large amounts can cause
nephritis, vomiting, diarrhea, circulatory
collapse, anemia, convulsions, and death.
Can cause kidney irritation and injury to
cornea and lens of the eye. Combustible
when exposed to heat or flame. When
heated to decomposition it emits acrid
smoke and irritating fumes. | | Synthesis | To a 10 mL pressure vessel, aryl halide (1.00 mmol), copper (I) oxide (0.05 mol), ligand (0.05 mol), 3 M sodium hydroxide (2 mL), and organic solvent (2 mL) were added. The reaction mixture was irradiated at 160 °C for 10 min with strong stirring. The reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a plug of celite in a fritted filter funnel and washed with ethyl acetate. The product was extracted using 30 mL of ethyl acetate for three times. The organic extract is washed three times with 10 mL water and two times with 10 mL of brine. The combined organic phases were dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to afford 1-naphthol. | | Purification Methods | Sublime 1-naphthol, then crystallise it from aqueous MeOH (charcoal), aqueous 25% or 50% EtOH, *C6H6, cyclohexane, heptane, CCl4 or H2O. Dry it over P2O5 in vacuo. The 4-nitrobenzoate has m 143o (from EtOH). [Shizuka et al. J Am Chem Soc 107 7816 1985, Beilstein 8 H 596, 6 IV 4208.] |
| | 1-Naphthol Preparation Products And Raw materials |
| Raw materials | Sulfuric acid-->Naphthalene-->1-Naphthylamine-->Naphthalene-2-sulfonic acid-->1,2,3,4-Tetrahydronaphthalene-->2-Ethylnitrobenzene-->Ammonium hydrogen sulfate-->1-Chloronaphthalene-->1-Naphthalenesulfonic acid-->Molybdic acid | | Preparation Products | NAPROANILIDE-->1,4-Naphthoquinone-->Eriochrome Black T-->Napropamide-->2-Ethoxynaphthalene-1-carbonyl chloride-->17-Ethinyl-17-hydroxy-18-methylestra-5(10),9(11)-dien-3-one-3-ethylene ketal-->ETHYL 3-(6-METHOXY-2-NAPHTHYL)-3-METHYL GLYCIDATE-->2-Nitroso-1-naphthol-->METHYL 3-(6-METHOXY-2-NAPHTHYL)-3-METHYL GLYCIDATE-->3-Methoxy-18-methylestra-2,5(10)dien-17-one 17-ethylene ketal-->6-methoxy-alpha-methylnaphthalen-1-acetaldehyde-->17-Ethinyl-3,17-dihydroxy-18-methylestra-2,5(10)-diene3-methylether-->3-Methoxy-18-methylestra-1,3,5(10),8-tetraen-17-ethylene ketal-->1-Hydroxy-2-naphthoic acid-->sodium 2-[(2-hydroxynaphthyl)azo]naphthalenesulphonate-->fluorescent whitening agent OM-->1-Ethenyl-1,2,3,4-tetrahydro-6-methoxy-1-naphthalenol-->13-Ethyl-17-hydroxy-18,19-dinorpregn-5(10)-en-20-yn-3-one-->N,N'-Di-2-naphthyl-p-phenylenediamine-->6'-Methoxy-2'-propiononaphthone-->2-BROMO-1-(6-METHOXY-2-NAPHTHALENYL)-1-PROPANONE-->FLAVIANIC ACID-->N-(1-Naphthyl)ethylenediamine dihydrochloride-->17-Ethynyl-18-methylestra-5(10),9(11)-dien-17-ol-3-one-->ACID RED 1-->1-NAPHTHOXYACETIC ACID-->2-[(1-Naphthyloxy)methyl]oxirane-->2-(1-Naphthalenyloxy)propanoic acid-->1-ETHOXYNAPHTHALENE-->Mordant Black 3-->5,8-Dihydronaphthol-->calcium disodium bis[2-chloro-5-[(2-hydroxy-1-naphthyl)azo]-4-sulphonatobenzoate]-->1-NAPHTHYL CHLOROFORMATE-->1-Nitroso-2-naphthol-->1,6-DIBROMO-2-METHOXYNAPHTHALENE-->4-Amino-1-naphthol hydrochloride-->1,6-Dibromo-2-naphthol-->O-2-Naphthyl chlorothioformate-->1-(6-hydroxy-2-naphthyl)ethan-1-one |
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