1-Naphthol

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1-Naphthol
Alpha-Naphthol.svg 1-Naphthol-3D-balls.png
Identifiers
CAS number 90-15-3 YesY
PubChem 7005
ChemSpider 6739 YesY
UNII 2A71EAQ389 YesY
KEGG C11714 YesY
ChEBI CHEBI:10319 YesY
ChEMBL CHEMBL122617 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H8O
Molar mass 144.17 g/mol
Appearance Colorless or white solid; commercial material is often strongly colored
Density 1.10 g/cm3
Melting point 95 to 96 °C (203 to 205 °F; 368 to 369 K)
Boiling point 278 to 280 °C (532 to 536 °F; 551 to 553 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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.[1]

Production[edit]

1-Naphthol is prepared by two main routes.[2] In one method, naphthalene is nitrated to give 1-nitronaphthalene, which is hydrogenated to the amine followed by hydrolysed:

C10H8 + 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[edit]

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.[3]

Applications[edit]

1-Naphthol is a precursor to a variety of insecticides including carbyl 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.[2]

Other uses[edit]

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.

References[edit]

  1. ^ Sreekanth, R; Prasanthkumar, KP; Sunil Paul, MM; Aravind, UK; Aravindakumar, CT (7 November 2013). "Oxidation reactions of 1- and 2-naphthols: an experimental and theoretical study.". The journal of physical chemistry. A 117 (44): 11261–70. doi:10.1021/jp4081355. PMID 24093754. Retrieved 2 December 2013. 
  2. ^ a b Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.
  3. ^ Meeker, John D.; Ryan, Louise; Barr, Dana B.; Hauser, Russ (January 2006). "Exposure to Nonpersistent Insecticides and Male Reproductive Hormones". Epidemiology 17 (1): 61–68. doi:10.1097/01.ede.0000190602.14691.70. PMID 16357596. 

External links[edit]