1-Naphthol

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]

1-Naphthol
Names
Preferred IUPAC name
Naphthalen-1-ol
Other names
1-Hydroxynaphthalene; 1-Naphthalenol; α-Naphthol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.791
KEGG
UNII
  • InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H checkY
    Key: KJCVRFUGPWSIIH-UHFFFAOYSA-N checkY
  • InChI=1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
    Key: KJCVRFUGPWSIIH-UHFFFAOYAZ
  • Oc2cccc1ccccc12
Properties
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)
-98.2·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Production

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 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 and degradation

Some reactions of 1-naphthol are explicable with reference to its tautomerism, which produces a small amount of the keto tautomer.

One consequence of this tautomerism is the Bucherer reaction, the ammonolysis of 1-naphthol to give 1-aminonaphthalene.

1-Naphthol biodegrades via formation of 1-naphthol-3,4-oxide, which converts to 1,4-naphthoquinone.[3]

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.[4][5]

Partial reduction of 1-naphthol gives the tetrahydro derivative, leaving intact the phenol ring.[6] Full hydrogenation is catalyzed by rhodium.[7]

Applications and occurrence

1-Naphthol is a precursor to a variety of insecticides including carbaryl and pharmaceuticals including nadolol[8][9] as well as for the antidepressant sertraline[10] and the anti-protozoan therapeutic atovaquone.[11] It undergoes azo coupling to give various azo dyes, but these are generally less useful than those derived from 2-naphthol.[2][12]

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.[13]

Other uses

1-Naphthol is used in each of the following chemical tests:

References
  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. Bibcode:2013JPCA..11711261S. doi:10.1021/jp4081355. PMID 24093754.
  2. Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009.. full-text PDF
  3. Yoshito Kumagai; Yasuhiro Shinkai; Takashi Miura; Arthur K. Cho (2011). "The Chemical Biology of Naphthoquinones and Its Environmental Implications". Annual Review of Pharmacology and Toxicology. 52: 221–47. doi:10.1146/annurev-pharmtox-010611-134517. PMID 21942631.
  4. J. B. Conant; R. E. Lutz; B. B. Corson (1923). "1,4-Aminonaphthol Hydrochloride". Organic Syntheses. 3: 7. doi:10.15227/orgsyn.003.0007.
  5. Louis F. Fieser (1937). "1,2-Aminonaphthol Hydrochloride". Organic Syntheses. 17: 9. doi:10.15227/orgsyn.017.0009.
  6. C. David Gutsche; Hugo H. Peter (1957). "Ar-Tetrahydro-a-Naphthol". Organic Syntheses. 37: 80. doi:10.15227/orgsyn.037.0080.
  7. A. I. Meyers; W. N. Beverung; R. Gault (1971). "Hydrogenation of Aromatic Nuclei: 1-Decalol". Organic Syntheses. 51: 103. doi:10.15227/orgsyn.051.0103.
  8. M.E. Condon; et al. (1978). "Nondepressant β-adrenergic blocking agents. 1. Substituted 3-amino-1-(5,6,7,8-tetrahydro-1-naphthoxy)-2-propanols". Journal of Medicinal Chemistry (in German). 21 (9): 913–922. doi:10.1021/jm00207a014. PMID 31485.
  9. DE 2258995, F.R. Hauck, C.M. Cimarusti, V.L. Narayan, "2,3-cis-1,2,3,4-Tetrahydro-5[2-hydroxy-3-(tert.-butylamino)-propoxy]-2,3-naphthalindiol", published 1973-06-07, assigned to E.R. Squibb & Sons, Inc.
  10. K. Vukics; T. Fodor; J. Fischer; I. Fellevári; S. Lévai (2002), "Improved industrial synthesis of antidepressant Sertraline", Org. Process Res. Dev. (in German), vol. 6, no. 1, pp. 82–85, doi:10.1021/op0100549
  11. B.N. Roy; G.P. Singh; P.S. Lathi; M.K. Agarwal (2013). "A novel process for synthesis of Atovaquone" (PDF). Indian J. Chem. (in German). 52B: 1299–1312. Archived from the original (PDF) on 30 May 2022.
  12. C. Kaiser; T. Jen; E. Garvey; W.D. Bowen; D.F. Colella; J.R. Wardell Jr. (1977). "Adrenergic agents. 4. Substituted phenoxypropanolamine derivatives as potential β-adrenergic agonists". Journal of Medicinal Chemistry (in German). 20 (5): 687–689. doi:10.1021/jm00215a014. PMID 16136.
  13. 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. S2CID 24829926.
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