1-Naphthol

1-Naphthol
Names
	Preferred IUPAC name Naphthalen-1-ol
	Other names 1-Hydroxynaphthalene; 1-Naphthalenol; α-Naphthol
Identifiers
CAS Number	90-15-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:10319 ;
ChEMBL	ChEMBL122617 ;
ChemSpider	6739 ;
ECHA InfoCard	100.001.791
KEGG	C11714 ;
PubChem CID	7005;
UNII	2A71EAQ389 ;
CompTox Dashboard (EPA)	DTXSID6021793 ;
	InChI InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H Key: KJCVRFUGPWSIIH-UHFFFAOYSA-N ; InChI=1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H Key: KJCVRFUGPWSIIH-UHFFFAOYAZ;
	SMILES Oc2cccc1ccccc12;
Properties
Chemical 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)
Magnetic susceptibility (χ)	-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).
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	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[]

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 + 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 and degradation[]

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]

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

Applications[]

1-Naphthol is a precursor to a variety of insecticides including carbaryl and pharmaceuticals including nadolol^[5]^[6] as well as for the antidepressant sertraline^[7] and the anti-protozoan therapeutic atovaquone.^[8] It undergoes azo coupling to give various azo dyes, but these are generally less useful than those derived from 2-naphthol.^[2]^[9]

Other uses[]

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

Molisch's test gives a red- or purple-colored compound to indicate the presence of carbohydrate.
The rapid furfural test turns purple quickly (<30s) if fructose is present, distinguishing it from glucose.
The Sakaguchi test turns red to indicate the presence of arginine in proteins.
The Voges–Proskauer test changes color from yellow to red to indicate that glucose is being broken down into acetoin which is used by bacteria for external energy storage.

References[]

^ 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.
^ ^a ^b Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.
^ 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.
^ 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.
^ 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", J. Med. Chem. (in German), 21 (9), pp. 913–922, doi:10.1021/jm00207a014
^ 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.
^ K. Vukics; T. Fodor; J. Fischer; I. Fellevári; S. Lévai (2002), "Improved industrial synthesis of antidepressant Sertraline", Org. Process Res. Dev. (in German), 6 (1), pp. 82–85, doi:10.1021/op0100549
^ 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, pp. 1299–1312
^ 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", J. Med. Chem. (in German), 20 (5), pp. 687–689, doi:10.1021/jm00215a014

External links[]

NIST Chemistry WebBook 1-Naphthalenol

[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.

[Ullmann-2] 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.

[4] 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.

[5] 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", J. Med. Chem. (in German), 21 (9), pp. 913–922, doi:10.1021/jm00207a014

[6] 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.

[7] K. Vukics; T. Fodor; J. Fischer; I. Fellevári; S. Lévai (2002), "Improved industrial synthesis of antidepressant Sertraline", Org. Process Res. Dev. (in German), 6 (1), pp. 82–85, doi:10.1021/op0100549

[8] 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, pp. 1299–1312

[9] 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", J. Med. Chem. (in German), 20 (5), pp. 687–689, doi:10.1021/jm00215a014

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