2-Phenylphenol: Difference between revisions
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! {{chembox header}}| '''{{{name|{{PAGENAME}}}}}''' |
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| Name = 2-Phenylphenol |
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| ImageFile = 2-Phenylphenol.svg |
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| ImageSize = 150px |
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| ImageFile1 = 2-Phenylphenol-from-xtal-Mercury-3D-bs.png |
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| [[IUPAC nomenclature|Chemical name]] |
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| ImageName = Ball-and-stick model of 2-Phenylphenol |
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| {{{IUPAC|2-phenylphenol}}} |
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| PIN = [1,1′-Biphenyl]-2-ol |
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| OtherNames = {{Unbulleted list|2-Phenylphenol|2-Biphenylol|''o''-Phenylphenol|Biphenylol|2-Hydroxybiphenyl|Orthophenyl phenol|''o''-Xenol|Orthoxenol}} |
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| Other names |
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|Section1={{Chembox Identifiers |
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| ''o''-phenylphenol<br>biphenylol<br>2-hydroxybiphenyl |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|- |
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| ChemSpiderID = 13839012 |
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| [[Chemical formula]] |
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| ChEBI = 17043 |
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| {{{formula|C<sub>12</sub>H<sub>14</sub>O}}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|- |
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| ChEMBL = 108829 |
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| [[Molecular mass]] |
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| EINECS = 201-993-5 |
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| {{{mol_mass|170.21}}} g/mol |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|- |
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| KEGG = D08367 |
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| [[CAS registry number|CAS number]] |
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| PubChem = 7017 |
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| [{{{CAS|90-43-7}}}] |
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| RTECS = DV5775000 |
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|- |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| [[Density]] |
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| UNII = D343Z75HT8 |
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| {{{density|1.293}}} g/cm<sup>3</sup> |
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| UNNumber = 3077 |
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|- |
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| InChI = 1/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H |
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| [[Melting point]] |
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| InChIKey = LLEMOWNGBBNAJR-UHFFFAOYAF |
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| {{{melting_point|55.5-57.5}}} °C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|- |
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| StdInChI = 1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H |
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| [[Boiling point]] |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| {{{boiling_point|280-284}}} °C |
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| StdInChIKey = LLEMOWNGBBNAJR-UHFFFAOYSA-N |
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|- |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| [[Simplified molecular input line entry specification|SMILES]] |
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| CASNo = 90-43-7 |
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| {{{SMILES|OC1=CC=CC=C1C2=CC=CC=C2}}} |
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| SMILES = Oc2ccccc2c1ccccc1 |
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|- |
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}} |
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| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small> |
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|Section2={{Chembox Properties |
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|- |
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| C=12 | H=10 | O=1 |
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|} |
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| Density = 1.293 g/cm<sup>3</sup> |
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| MeltingPtC = 55.5 to 57.5 |
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| BoilingPtC = 280 to 284 |
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}} |
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|Section6={{Chembox Pharmacology |
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| ATCCode_prefix = D08 |
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| ATCCode_suffix = AE06 |
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}} |
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|Section7={{Chembox Hazards |
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| GHS_ref=<ref>{{cite web |title=2-Phenylphenol |url=https://pubchem.ncbi.nlm.nih.gov/compound/7017#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=11 September 2022 |language=en}}</ref> |
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| GHSPictograms = {{GHS07}}{{GHS09}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335|400}} |
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| PPhrases = {{P-phrases|261|264|264+265|271|273|280|302+352|304+340|305+351+338|319|321|332+317|337+317|362+364|391|403+233|405|501}} |
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}} |
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}} |
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'''2-Phenylphenol''', or ''o''-phenylphenol, is an [[organic compound]]. In terms of structure, it is one of the monohydroxylated isomers of [[biphenyl]].<ref>{{cite book|editor-last=O'Neil|editor-first=M.J.|title=Merck Index : an encyclopedia of chemicals, drugs, & biologicals|year=2001|publisher=MERCK & CO INC|location=United States|isbn=0911910131|pages=[https://archive.org/details/merckindexency00onei/page/7388 7388]|edition=13th|url-access=registration|url=https://archive.org/details/merckindexency00onei/page/7388}}</ref><ref>{{cite book|last=Budavari|first=Susan|title=The Merck index an encyclopedia of chemicals, drugs, and biologicals|year=1997|publisher=Merck|location=Whitehouse Station, NJ|isbn=0911910123|pages=7458|edition=12th, 2nd printing}}</ref> It is a white solid. It is a [[biocide]] used as a [[preservative]] with E number E231 and under the trade names Dowicide, Torsite, Fungal, Preventol, Nipacide and many others. |
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'''2-Phenylphenol''', or ''o''-phenylphenol, is an [[organic compound]] that consists of two linked [[benzene]] rings and a [[phenol]]ic hydroxyl group. It is a white or buff-colored, flaky crystalline solid with a melting point of about 57 °C. |
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==Uses== |
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The primary use of 2-phenylphenol is as an agricultural fungicide. It is generally applied post-harvest. It is also used in the manufacture of other fungicides, dye stuffs, and rubber chemicals. |
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The primary use of 2-phenylphenol is as an agricultural fungicide. It is generally applied post-harvest. It is a [[fungicide]] used for waxing [[citrus fruit]]s. It is no longer a permitted [[food additive]] in the European Union, but is still allowed as a post-harvest treatment in 4 EU countries.<ref>{{Ullmann |doi=10.1002/14356007.a16_563.pub2|title=Biocides |year=2013 |last1=Uhr |first1=Hermann |last2=Mielke |first2=Burkhard |last3=Exner |first3=Otto |last4=Payne |first4=Ken R. |last5=Hill |first5=Edward |pages=1–26 |isbn=9783527306732 }}</ref> |
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It is also used for disinfection of seed boxes. It is a general surface [[disinfectant]], used in households, hospitals, nursing homes, farms, laundries, barber shops, and food processing plants. It can be used on fibers and other materials. It is used to [[disinfect]] hospital and veterinary equipment. Other uses are in rubber industry and as a laboratory reagent. It is also used in the manufacture of other fungicides, dye stuffs, resins and rubber chemicals. |
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2-Phenylphenol is found in low concentrations in some household products such as spray disinfectants and aerosol or spray underarm deodorants. |
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2-Phenylphenol is a precursor to [[9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide|9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide]], a commercial [[fire retardant]]. |
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Eye contact can cause severe irritation and burns with possible eye damage. For some individuals, 2-phenylphenol can also irritate the skin. |
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The sodium salt of orthophenyl phenol, [[sodium orthophenyl phenol]], is a [[preservative]], used to treat the surface of [[citrus]] [[fruit]]s.<ref>{{cite web|title=Environmental Fate and Exposure Potential|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=14709584|work=2-Phenylphenol - Substance Summary|publisher=National Center for Biotechnology Information, U.S. National Library of Medicine|access-date=2 June 2012}}</ref> |
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Orthophenyl phenol is also used as a fungicide in food packaging and may migrate into the contents.<ref>{{cite journal |author1=Mehmet Coelhan |author2=Karl-Heinz Bromig |author3=Karl Glas |author4=A. Lynn Roberts | doi = 10.1021/jf060743p | pmid = 16881670 | title = Determination and Levels of the Biocide ortho-Phenylphenol in Canned Beers from Different Countries | journal = J. Agric. Food Chem. | year = 2006 | volume = 54 | issue = 16 | pages = 5731–5735}}</ref> |
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==Preparation== |
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It is prepared by condensation of [[cyclohexanone]] to give cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol.<ref name=Ullmann/> |
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==Safety== |
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[[LD50]] (rats) is 2700 to 3000 mg/kg.<ref name=Ullmann>{{Ullmann| author1=Helmut Fiege | author2=Heinz-Werner Voges | author3=Toshikazu Hamamoto | author4=Sumio Umemura | author5=Tadao Iwata | author6=Hisaya Miki | author7=Yasuhiro Fujita | author8=Hans-Josef Buysch | author9=Dorothea Garbe | author10=Wilfried Paulus | contribution=Phenol Derivatives | year=2007 | doi=10.1002/14356007.a19_313}}</ref> |
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==References== |
==References== |
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{{Reflist}} |
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* ''Merck Index'', 12th Edition, '''7458'''. |
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{{Refbegin}} |
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*[http://www.state.nj.us/health/eoh/rtkweb/1439.pdf Hazardous Substance Fact Sheet] |
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{{Refend}} |
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==External links== |
==External links== |
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*[http://www.scorecard.org/chemical-profiles/pesticides.tcl?edf_substance_id=90-43-7 List of brand name products which contain 2-phenylphenol] |
* [http://www.scorecard.org/chemical-profiles/pesticides.tcl?edf_substance_id=90-43-7 List of brand name products which contain 2-phenylphenol] {{Webarchive|url=https://web.archive.org/web/20050826225342/http://www.scorecard.org/chemical-profiles/pesticides.tcl?edf_substance_id=90-43-7 |date=2005-08-26 }} |
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* [https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=14709584 National Center for Biotechnology Information 2-Phenylphenol - Substance Summary] |
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{{DEFAULTSORT:Phenylphenol, 2-}} |
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[[Category:Phenols]] |
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[[Category:2-Hydroxyphenyl compounds]] |
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[[Category:Household chemicals]] |
[[Category:Household chemicals]] |
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[[Category:Fungicides]] |
[[Category:Fungicides]] |
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[[Category:Antiseptics]] |
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[[Category:Fumigants]] |
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[[Category:Preservatives]] |
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[[Category:Biphenyls]] |
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Latest revision as of 01:04, 25 December 2024
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| Names | |
|---|---|
| Preferred IUPAC name
[1,1′-Biphenyl]-2-ol | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.812 |
| EC Number |
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| E number | E231 (preservatives) |
| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 3077 |
CompTox Dashboard (EPA)
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| Properties | |
| C12H10O | |
| Molar mass | 170.211 g·mol−1 |
| Density | 1.293 g/cm3 |
| Melting point | 55.5 to 57.5 °C (131.9 to 135.5 °F; 328.6 to 330.6 K) |
| Boiling point | 280 to 284 °C (536 to 543 °F; 553 to 557 K) |
| Pharmacology | |
| D08AE06 (WHO) | |
| Hazards | |
| GHS labelling:[1] | |
 
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| Warning | |
| H315, H319, H335, H400 | |
| P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Phenylphenol, or o-phenylphenol, is an organic compound. In terms of structure, it is one of the monohydroxylated isomers of biphenyl.[2][3] It is a white solid. It is a biocide used as a preservative with E number E231 and under the trade names Dowicide, Torsite, Fungal, Preventol, Nipacide and many others.
Uses
[edit]The primary use of 2-phenylphenol is as an agricultural fungicide. It is generally applied post-harvest. It is a fungicide used for waxing citrus fruits. It is no longer a permitted food additive in the European Union, but is still allowed as a post-harvest treatment in 4 EU countries.[4]
It is also used for disinfection of seed boxes. It is a general surface disinfectant, used in households, hospitals, nursing homes, farms, laundries, barber shops, and food processing plants. It can be used on fibers and other materials. It is used to disinfect hospital and veterinary equipment. Other uses are in rubber industry and as a laboratory reagent. It is also used in the manufacture of other fungicides, dye stuffs, resins and rubber chemicals.
2-Phenylphenol is a precursor to 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, a commercial fire retardant.
The sodium salt of orthophenyl phenol, sodium orthophenyl phenol, is a preservative, used to treat the surface of citrus fruits.[5]
Orthophenyl phenol is also used as a fungicide in food packaging and may migrate into the contents.[6]
Preparation
[edit]It is prepared by condensation of cyclohexanone to give cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol.[7]
Safety
[edit]LD50 (rats) is 2700 to 3000 mg/kg.[7]
References
[edit]- ^ "2-Phenylphenol". pubchem.ncbi.nlm.nih.gov. Retrieved 11 September 2022.
- ^ O'Neil, M.J., ed. (2001). Merck Index : an encyclopedia of chemicals, drugs, & biologicals (13th ed.). United States: MERCK & CO INC. pp. 7388. ISBN 0911910131.
- ^ Budavari, Susan (1997). The Merck index an encyclopedia of chemicals, drugs, and biologicals (12th, 2nd printing ed.). Whitehouse Station, NJ: Merck. p. 7458. ISBN 0911910123.
- ^ Uhr, Hermann; Mielke, Burkhard; Exner, Otto; Payne, Ken R.; Hill, Edward (2013). "Biocides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–26. doi:10.1002/14356007.a16_563.pub2. ISBN 9783527306732.
- ^ "Environmental Fate and Exposure Potential". 2-Phenylphenol - Substance Summary. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2 June 2012.
- ^ Mehmet Coelhan; Karl-Heinz Bromig; Karl Glas; A. Lynn Roberts (2006). "Determination and Levels of the Biocide ortho-Phenylphenol in Canned Beers from Different Countries". J. Agric. Food Chem. 54 (16): 5731–5735. doi:10.1021/jf060743p. PMID 16881670.
- ^ a b Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe; Wilfried Paulus (2007). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.