Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1-Naphthol: Difference between pages

| verifiedrevid = 477188585

|ImageFileL1=alpha-Naphthol.svg

|ImageFileR1=1-Naphthol-3D-balls.png

|PIN=Naphthalen-1-ol

|OtherNames=1-Hydroxynaphthalene; 1-Naphthalenol; α-Naphthol

|Section1={{chembox Identifiers

| Beilstein = 1817321

| UNII_Ref = {{fdacite|correct|FDA}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| EC_number = 201-969-4

| Gmelin = 69192

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| PubChem=7005

| SMILES = Oc2cccc1ccccc12

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

|Section2={{chembox Properties

| Formula={{chem2|C10H8O}}

| MolarMass=144.17 g/mol

| Appearance=Colorless or white solid

| Density=1.10 g/cm³

| MeltingPtC=95 to 96

| BoilingPtC=278 to 280

| Solubility=

| MagSus = -98.2·10⁻⁶ cm³/mol

|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>

| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}}

| GHSSignalWord = Danger

| 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 a [[organic compound]] with the formula {{chem2|C10H7OH}}. It is a [[fluorescence|fluorescent]] white solid. 1-Naphthol differs from its [[isomer]] [[2-Naphthol|2-naphthol]] by the location of the [[hydroxide|hydroxyl group]] on the [[naphthalene]] ring. The naphthols are naphthalene homologues of [[phenol]]. Both isomers are soluble in simple [[organic solvents]]. 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 [[tetralin]], which is oxidized to [[1-tetralone]], which undergoes [[dehydrogenation]].

==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}}

:[[File:Alpha-naphthol tautomerism.svg|frameless|left|384px]]

{{clear left}}

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

1-Naphthol biodegrades via formation of [[arene oxide|1-naphthol-3,4-oxide]], which converts to [[1,4-Naphthoquinone|1,4-naphthoquinone]].<ref>{{cite journal|journal=[[Annual Review of Pharmacology and Toxicology]]|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 [[diazonium salt]]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 [[carbaryl]] and pharmaceuticals including [[nadolol]]<ref>{{cite journal|surname1=M.E. Condon|display-authors=et al|journal=[[Journal of Medicinal Chemistry]]|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-hydroxy-3-(tert.-butylamino)-propoxy]-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 [[antidepressant]] [[sertraline]]<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 [[Antiprotozoal|anti-protozoan]] therapeutic [[atovaquone]].<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 [[azo coupling]] to give various [[azo dye]]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}}. [https://pdfslide.net/documents/ullmanns-encyclopedia-of-industrial-chemistry-naphthalene-derivatives.html '''full-text PDF''']</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=[[Journal of Medicinal Chemistry]]|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 [[carbaryl]] and [[naphthalene]]. Along with [[TCPy]], it has been shown to decrease testosterone levels in adult men.<ref>{{cite journal | journal = [[Epidemiology (journal)|Epidemiology]] | 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:

* [[Molisch's test]] gives a red- or purple-colored compound to indicate the presence of [[carbohydrate]].

* [[rapid furfural test]] turns purple quickly (<30s) if [[fructose]] is present, distinguishing it from glucose.

* [[Sakaguchi test]] turns red to indicate the presence of [[arginine]] in proteins.

* [[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.

==Safety==

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

==References==

{{reflist}}

==External links==

*[http://webbook.nist.gov/cgi/cbook.cgi?Name=1-naphthol&Units=SI NIST Chemistry WebBook 1-Naphthalenol]

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

{{DEFAULTSORT:Naphthol, 1-}}

[[Category:1-Naphthols| ]]

[[Category:1-Naphthyl compounds]]