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;
Beilstein Reference	1817321
ChEBI	CHEBI:10319;
ChEMBL	ChEMBL122617;
ChemSpider	6739;
ECHA InfoCard	100.001.791
EC Number	201-969-4;
Gmelin Reference	69192
KEGG	C11714;
PubChemCID	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
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)	-98.2·10−6cm3/mol
Hazards
	GHSlabelling:
Pictograms
Signal word	Danger
Hazard statements	H302,H311,H312,H315,H317,H318,H335,H410,H412
Precautionary statements	P261,P262,P264,P264+P265,P270,P271,P272,P273,P280,P301+P317,P302+P352,P304+P340,P305+P354+P338,P316,P317,P319,P321,P330,P332+P317,P333+P317,P361+P364,P362+P364,P391,P403+P233,P405,P501
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). verify(what is?) Infobox references

1-Naphthol,orα-naphthol,is anorganic compoundwith the formulaC₁₀H₇OH.It is afluorescentwhite solid. 1-Naphthol differs from itsisomer 2-naphtholby the location of thehydroxyl groupon thenaphthalenering. The naphthols are naphthalene homologues ofphenol.Both isomers are soluble in simpleorganic solvents.They are precursors to a variety of useful compounds.^[2]

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 totetralin,which is oxidized to1-tetralone,which undergoesdehydrogenation.

Reactions

Some reactions of 1-naphthol are explicable with reference to its tautomerism, which produces a small amount of the keto tautomer.^{[citation needed]}

One consequence of this tautomerism is theBucherer reaction,the ammonolysis of 1-naphthol to give1-aminonaphthalene.

1-Naphthol biodegrades via formation of1-naphthol-3,4-oxide,which converts to1,4-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 usingdiazonium 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 includingcarbaryland pharmaceuticals includingnadolol^[8]^[9]as well as for theantidepressant sertraline^[10]and theanti-protozoantherapeuticatovaquone.^[11]It undergoesazo couplingto give variousazo dyes,but these are generally less useful than those derived from 2-naphthol.^[2]^[12]

1-Naphthol is a metabolite of the insecticidecarbarylandnaphthalene.Along withTCPy,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, which predate the use of spectroscopic and chromatographic methods:

Molisch's testgives a red- or purple-colored compound to indicate the presence ofcarbohydrate.
rapid furfural testturns purple quickly (<30s) iffructoseis present, distinguishing it from glucose.
Sakaguchi testturns red to indicate the presence ofargininein proteins.
Voges–Proskauer testchanges color from yellow to red to indicate thatglucoseis being broken down intoacetoinwhich is used by bacteria for external energy storage.

Safety

1-Naphthol has been described as "moderately toxic".^[2]

References

^"1-Naphthol".pubchem.ncbi.nlm.nih.gov.
^^a ^b ^c ^dBooth, Gerald (2005). "Naphthalene Derivatives".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a17_009.ISBN 978-3-527-30673-2..full-text PDF
^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.
^J. B. Conant; R. E. Lutz; B. B. Corson (1923). "1,4-Aminonaphthol Hydrochloride".Organic Syntheses.3:7.doi:10.15227/orgsyn.003.0007.
^Louis F. Fieser (1937). "1,2-Aminonaphthol Hydrochloride".Organic Syntheses.17:9.doi:10.15227/orgsyn.017.0009.
^C. David Gutsche; Hugo H. Peter (1957). "Ar-Tetrahydro-a-Naphthol".Organic Syntheses.37:80.doi:10.15227/orgsyn.037.0080.
^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.
^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.
^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), vol. 6, no. 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:1299–1312. Archived fromthe original(PDF)on 30 May 2022.
^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.
^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.

External links

NIST Chemistry WebBook 1-Naphthalenol
"Napthols".Encyclopædia Britannica.Vol. 19 (11th ed.). 1911. pp.168–169.

[1] "1-Naphthol".pubchem.ncbi.nlm.nih.gov.

[Ullmann-2] Booth, Gerald (2005). "Naphthalene Derivatives".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a17_009.ISBN 978-3-527-30673-2..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 fromthe 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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