Trisha Shetty (Editor)

1 Naphthol

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Formula  C10H8O
Density  1.1 g/cm³
Molar mass  144.17 g/mol
1-Naphthol wwwsigmaaldrichcomcontentdamsigmaaldrichstr
Appearance  Colorless or white solid; commercial material is often strongly colored

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.

Contents

1-Naphthol 2Nitro1naphthol 95 SigmaAldrich

Production

1-Naphthol 1Naphthol C10H8O ChemSpider

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:

1-Naphthol 1naphthol Critically Evaluated Thermophysical Property Data fromC10H8 + HNO3 → C10H7NO2 + H2O C10H7NO2 + 3 H2 → C10H7NH2 + 2 H2O C10H7NH2 + H2O → C10H7OH + NH3

Alternatively, naphthalene is hydrogenated to tetralin, which is oxidized to 1-tetralone, which undergoes dehydrogenation.

Occurrence

1-Naphthol 1naphthol C10H8O ChemSynthesis

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.

Applications

1-Naphthol FileAryl1Naththyl1Naphtholpng Wikimedia Commons

1-Naphthol is a precursor to a variety of insecticides including carbaryl and pharmaceuticals including nadolol. It undergoes azo coupling to give various azo dyes, but these are generally less useful than those derived from 2-naphthol.

Other uses

In Molisch's test, 1-naphthol dissolved in ethanol, known as Molisch's reagent, is used as reagent for detecting the presence of carbohydrates. The test known as Molisch's test would give a red- or purple-colored compound to indicate the presence of carbohydrate. The rapid furfural test, similar to Molisch's test, also uses 1-naphthol.

The Sakaguchi test uses 1-naphthol with sodium hypobromite to detect the presence of arginine in proteins.

The Voges–Proskauer test uses 1-naphthol in potassium hydroxide (KOH) solution to detect the breakdown of glucose into acetoin which is used by bacteria for external energy storage. A positive test will be indicated by the appearance of a red color of the original yellow solution.

1-Naphthol

References

1-Naphthol Wikipedia


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