-
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
-
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.
-
Uses
1-Naphthol has been used as a prooxidant to analyze its ability to induce hemolysis in a zebrafish G6PD (glucose-6-phosphate dehydrogenase) deficiency model.
-
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.
-
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.
-
Definition
ChEBI: A naphthol carrying a hydroxy group at position 1.
-
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.
-
Contact allergens
Alpha-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.
-
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.]
