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Revision as of 14:32, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477177494 of page 1-Naphthol for the Chem/Drugbox validation project (updated: '').  Latest revision as of 00:16, 3 January 2025 edit Swinub (talk | contribs)Extended confirmed users66,038 editsm Grammar 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
⚫ | verifiedrevid = 477188585
| Verifiedfields fdofdhfff
|ImageFileL1=alpha-Naphthol.svg
⚫ | verifiedrevid = 457306535
|ImageFile=alpha-Naphthol.svg |ImageFileR1=1-Naphthol-3D-balls.png
⚫ |PIN=Naphthalen-1-ol
|ImageSize=150px
⚫ |OtherNames=1-Hydroxynaphthalene; 1-Naphthalenol; α-Naphthol
|ImageFile1=1-Naphthol-3D-balls.png
⚫ |Section1={{chembox Identifiers
|ImageSize1=180px
| Beilstein = 1817321
⚫ |IUPACName=Naphthalen-1-ol
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ |OtherNames=1-Hydroxynaphthalene; 1-Naphthalenol; ''alpha''-Naphthol
⚫ |Section1={{Chembox Identifiers
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2A71EAQ389 | UNII = 2A71EAQ389
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
Line 18: Line 14:
| InChI = 1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H | InChI = 1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
| InChIKey = KJCVRFUGPWSIIH-UHFFFAOYAZ | InChIKey = KJCVRFUGPWSIIH-UHFFFAOYAZ
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 122617 | ChEMBL = 122617
| EC_number = 201-969-4
⚫ | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| Gmelin = 69192
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H | StdInChI = 1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KJCVRFUGPWSIIH-UHFFFAOYSA-N | StdInChIKey = KJCVRFUGPWSIIH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=90-15-3 | CASNo=90-15-3
| PubChem=7005 | PubChem=7005
| SMILES = Oc2cccc1ccccc12 | SMILES = Oc2cccc1ccccc12
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 10319 | ChEBI = 10319
| ChemSpiderID=6739 | ChemSpiderID=6739
}} }}
|Section2={{Chembox Properties |Section2={{chembox Properties
| Formula=C<sub>10</sub>H<sub>8</sub>O | Formula={{chem2|C10H8O}}
| MolarMass=144.17 g/mol | MolarMass=144.17 g/mol
| Appearance=Colorless or white solid; commercial material is often strongly colored | Appearance=Colorless or white solid
| Density=1.10 g/cm<sup>3</sup> | Density=1.10 g/cm<sup>3</sup>
| MeltingPtC=95 to 96
| MeltingPt=95–96&nbsp;°C
| BoilingPtC=278 to 280
| BoilingPt=278–280&nbsp;°C
| Solubility= | Solubility=
| MagSus = -98.2·10<sup>−6</sup> cm<sup>3</sup>/mol
}} }}
|Section3={{Chembox Hazards |Section3={{chembox Hazards
| GHS_ref=<ref>{{cite web |title=1-Naphthol |url=https://pubchem.ncbi.nlm.nih.gov/compound/7005#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
⚫ | MainHazards=
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}}
⚫ | FlashPt=
| GHSSignalWord = Danger
| Autoignition=
| HPhrases = {{H-phrases|302|311|312|315|317|318|335|410|412}}
| PPhrases = {{P-phrases|261|262|264|264+265|270|271|272|273|280|301+317|302+352|304+340|305+354+338|316|317|319|321|330|332+317|333+317|361+364|362+364|391|403+233|405|501}}
⚫ | MainHazards=
⚫ | FlashPt=
| AutoignitionPt=
}} }}
}} }}

'''1-Naphthol''', or '''α-naphthol''', is an ] with the formula {{chem2|C10H7OH}}. It is a ] white solid. 1-Naphthol differs from its ] ] by the location of the ] on the ] ring. The naphthols are naphthalene homologues of ]. Both isomers are soluble in simple ]. They are precursors to a variety of useful compounds.<ref name=Ullmann/>

==Production==
1-Naphthol is prepared by two main routes.<ref name=Ullmann/> In one method, naphthalene is nitrated to give 1-nitronaphthalene, which is hydrogenated to the amine followed by hydrolysis:
: {{chem2|C10H8 + HNO3 -> C10H7NO2 + H2O}}
: {{chem2|C10H7NO2 + 3H2 -> C10H7NH2 + 2H2O}}
: {{chem2|C10H7NH2 + H2O -> C10H7OH + NH3}}

Alternatively, naphthalene is hydrogenated to ], which is oxidized to ], which undergoes ].

==Reactions==
Some reactions of 1-naphthol are explicable with reference to its tautomerism, which produces a small amount of the keto tautomer.{{citation needed|date=August 2024}}
:]
{{clear left}}
One consequence of this tautomerism is the ], the ammonolysis of 1-naphthol to give ].

1-Naphthol biodegrades via formation of ], which converts to ].<ref>{{cite journal|journal=]|year=2011|title=The Chemical Biology of Naphthoquinones and Its Environmental Implications|author1=Yoshito Kumagai|author2=Yasuhiro Shinkai|author3= Takashi Miura|author4=Arthur K. Cho| author4-link=Arthur K. Cho|volume=52|doi=10.1146/annurev-pharmtox-010611-134517|pmid=21942631|pages=221–47}}</ref>

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 ]s. Reduction of the diazo derivatives gives 4-amino-1-naphthol.<ref>{{cite journal |doi=10.15227/orgsyn.003.0007|title=1,4-Aminonaphthol Hydrochloride|author1=J. B. Conant|author2=R. E. Lutz|author3=B. B. Corson |journal=Organic Syntheses |year=1923 |volume=3 |page=7 }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.017.0009|title=1,2-Aminonaphthol Hydrochloride |journal=Organic Syntheses |year=1937 |volume=17 |page=9 |author=Louis F. Fieser}}</ref>

Partial reduction of 1-naphthol gives the tetrahydro derivative, leaving intact the phenol ring.<ref>{{cite journal |doi=10.15227/orgsyn.037.0080|title=Ar-Tetrahydro-a-Naphthol |journal=Organic Syntheses |year=1957 |volume=37 |page=80 |author1= C. David Gutsche |author2=Hugo H. Peter}}</ref> Full hydrogenation is catalyzed by rhodium.<ref>{{cite journal |doi=10.15227/orgsyn.051.0103|title=Hydrogenation of Aromatic Nuclei: 1-Decalol |journal=Organic Syntheses |year=1971 |volume=51 |page=103|author1=A. I. Meyers|author2=W. N. Beverung|author3=R. Gault}}</ref>

==Applications and occurrence==
1-Naphthol is a precursor to a variety of insecticides including ] and pharmaceuticals including ]<ref>{{cite journal|surname1=M.E. Condon|display-authors=et al|journal=]|title=Nondepressant β-adrenergic blocking agents. 1. Substituted 3-amino-1-(5,6,7,8-tetrahydro-1-naphthoxy)-2-propanols|volume=21|issue=9|pages=913–922|date=1978|language=German|doi=10.1021/jm00207a014
|pmid=31485 }}</ref><ref>{{Cite patent|country = DE|number =2258995 |title=2,3-cis-1,2,3,4-Tetrahydro-5-2,3-naphthalindiol |pubdate =1973-06-07 |fdate =1972-12-01 |invent1 =F.R. Hauck, C.M. Cimarusti, V.L. Narayan | assign =E.R. Squibb & Sons, Inc.}}</ref> as well as for the ] ]<ref>{{citation|author1=K. Vukics|author2= T. Fodor|author3= J. Fischer|author4= I. Fellevári|author5= S. Lévai|periodical=Org. Process Res. Dev.|title=Improved industrial synthesis of antidepressant Sertraline|volume=6|issue=1|pages=82–85|date= 2002|language=German|doi=10.1021/op0100549
}}</ref> and the ] therapeutic ].<ref>{{cite journal|author1=B.N. Roy|author2= G.P. Singh|author3= P.S. Lathi|author4= M.K. Agarwal|journal=Indian J. Chem.|title=A novel process for synthesis of Atovaquone|volume=52B|pages=1299–1312|date=2013|language=German |archive-url=https://web.archive.org/web/20220530185938/http://nopr.niscair.res.in/bitstream/123456789/21838/1/IJCB%2052B(10)%201299-1312.pdf |df=dmy-all |archive-date=2022-05-30 |url=http://nopr.niscair.res.in/bitstream/123456789/21838/1/IJCB%2052B%2810%29%201299-1312.pdf}}</ref> It undergoes ] to give various ]s, but these are generally less useful than those derived from 2-naphthol.<ref name=Ullmann>{{Ullmann|first=Gerald|last=Booth|title=Naphthalene Derivatives|year=2005|doi=10.1002/14356007.a17_009}}. </ref><ref>{{cite journal|author1=C. Kaiser|author2= T. Jen|author3= E. Garvey|author4= W.D. Bowen|author5= D.F. Colella|author6= J.R. Wardell Jr.|periodical=]|title=Adrenergic agents. 4. Substituted phenoxypropanolamine derivatives as potential β-adrenergic agonists|volume=20|issue=5|pages=687–689|date=1977|language=German|doi=10.1021/jm00215a014|pmid=16136}}</ref>

1-Naphthol is a metabolite of the insecticide ] and ]. Along with ], it has been shown to decrease testosterone levels in adult men.<ref>{{cite journal | journal = ] | volume =17 | issue=1 | pages = 61–68 | title = Exposure to Nonpersistent Insecticides and Male Reproductive Hormones |author1=Meeker, John D. |author2=Ryan, Louise |author3=Barr, Dana B. |author4=Hauser, Russ | doi = 10.1097/01.ede.0000190602.14691.70 | pmid = 16357596 |date= January 2006 | s2cid =24829926| doi-access =free }}</ref>

===Other uses===
1-Naphthol is used in each of the following chemical tests, which predate the use of spectroscopic and chromatographic methods:
* ] gives a red- or purple-colored compound to indicate the presence of ].
* ] turns purple quickly (<30s) if ] is present, distinguishing it from glucose.
* ] turns red to indicate the presence of ] in proteins.
* ] changes color from yellow to red to indicate that ] is being broken down into ] which is used by bacteria for external energy storage.

==Safety==
1-Naphthol has been described as "moderately toxic".<ref name=Ullmann/>

==References==
{{reflist}}

==External links==
*
* {{cite EB1911 |wstitle=Napthols |volume=19 |pages=168–169 |short=1}}

{{DEFAULTSORT:Naphthol, 1-}}
]
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