2-Phenylphenol

2-Phenylphenol
Ball-and-stick model of 2-Phenylphenol
Names
Preferred IUPAC name
[1,1′-Biphenyl]-2-ol
Other names
  • 2-Phenylphenol
  • 2-Biphenylol
  • o-Phenylphenol
  • Biphenylol
  • 2-Hydroxybiphenyl
  • Orthophenyl phenol
  • o-Xenol
  • Orthoxenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.812 Edit this at Wikidata
EC Number
  • 201-993-5
E number E231 (preservatives)
KEGG
RTECS number
  • DV5775000
UNII
UN number 3077
  • InChI=1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H checkY
    Key: LLEMOWNGBBNAJR-UHFFFAOYSA-N checkY
  • InChI=1/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H
    Key: LLEMOWNGBBNAJR-UHFFFAOYAF
  • Oc2ccccc2c1ccccc1
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]
GHS07: Exclamation markGHS09: Environmental hazard
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).
☒N verify (what is checkY☒N ?)

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

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

It is prepared by condensation of cyclohexanone to give cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol.[7]

Safety

LD50 (rats) is 2700 to 3000 mg/kg.[7]

References

  1. ^ "2-Phenylphenol". pubchem.ncbi.nlm.nih.gov. Retrieved 11 September 2022.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ "Environmental Fate and Exposure Potential". 2-Phenylphenol - Substance Summary. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2 June 2012.
  6. ^ 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.
  7. ^ 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.