:2-Phenylphenol
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 407466211
| Name = 2-Phenylphenol
| ImageFile = 2-Phenylphenol.svg
| ImageSize = 150px
| ImageFile1 = 2-Phenylphenol-from-xtal-Mercury-3D-bs.png
| ImageName = Ball-and-stick model of 2-Phenylphenol
| PIN = [1,1′-Biphenyl]-2-ol
| OtherNames = {{Unbulleted list|2-Phenylphenol|2-Biphenylol|o-Phenylphenol|Biphenylol|2-Hydroxybiphenyl|Orthophenyl phenol|o-Xenol|Orthoxenol}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13839012
| ChEBI = 17043
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 108829
| EINECS = 201-993-5
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08367
| PubChem = 7017
| RTECS = DV5775000
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = D343Z75HT8
| UNNumber = 3077
| InChI = 1/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H
| InChIKey = LLEMOWNGBBNAJR-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LLEMOWNGBBNAJR-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 90-43-7
| SMILES = Oc2ccccc2c1ccccc1
}}
|Section2={{Chembox Properties
| C=12 | H=10 | O=1
| Density = 1.293 g/cm3
| MeltingPtC = 55.5 to 57.5
| BoilingPtC = 280 to 284
}}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = D08
| ATCCode_suffix = AE06
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335|400}}
| 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}}
}}
}}
2-Phenylphenol, or o-phenylphenol, is an organic compound. In terms of structure, it is one of the monohydroxylated isomers of biphenyl.{{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}}{{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}} 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
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.{{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 }}
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.{{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}}
Orthophenyl phenol is also used as a fungicide in food packaging and may migrate into the contents.{{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|bibcode=2006JAFC...54.5731C }}
Preparation
It is prepared by condensation of cyclohexanone to give cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol.
Safety
LD50 (rats) is 2700 to 3000 mg/kg.{{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}}
References
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External links
- [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 }}
- [https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=14709584 National Center for Biotechnology Information 2-Phenylphenol - Substance Summary]
{{DEFAULTSORT:Phenylphenol, 2-}}