4-Phenylphenol

4-Phenylphenol

Names
IUPAC name 4-phenylphenol
Other names 4-Hydroxybiphenyl; 4-Phenylphenol; (1,1'-Biphenyl)-4-ol; 1-Hydroxy-4-phenylbenzene; 4-Biphenylol; 4-Diphenylol; 4-Hydroxydiphenyl
Identifiers
CAS Number	92-69-3  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34422
ChEMBL	ChEMBL73380
ChemSpider	13846658
ECHA InfoCard	100.001.982
EC Number	202-179-2
KEGG	C14224
PubChem CID	7103
UNII	50LH4BZ6MD  Y
CompTox Dashboard (EPA)	DTXSID7021152
InChI InChI=1S/C12H10O/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13H Key: YXVFYQXJAXKLAK-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C2=CC=C(C=C2)O
Properties
Chemical formula	C12H10O
Molar mass	170.211 g·mol−1
Melting point	164–165 °C (327–329 °F; 437–438 K)
Boiling point	305–308 °C (581–586 °F; 578–581 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H411
Precautionary statements	P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, 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). Infobox references

4-Phenylphenol is an organic compound with the formula C₆H₅−C₆H₄OH. It is one of three isomers of hydroxybiphenyl. ^[1]

Production

4-Phenylphenol is produced as a byproduct in the conversion of chlorobenzene to phenol with base. It can also be obtain by sulfonation of biphenyl to give 4-biphenylsulfonic acid, which can be hydrolyzed. ^[1]

Of academic interest, 4-phenylphenol can be obtained from the Suzuki coupling of phenylboronic acid with 4-iodophenol in the presence of 10% palladium on carbon and potassium carbonate. ^{[2] [3]}

Properties

4-Phenylphenol is a flammable, difficult to ignite, white, scaly solid with a phenol-like odor that is very slightly soluble in water. ^[4]

References

1. Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; et al. (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN   3527306730.
2. Sakurai, Hidehiro; Tsukuda, Tatsuya; Hirao, Toshikazu (1 April 2002). "Pd/C as a Reusable Catalyst for the Coupling Reaction of Halophenols and Arylboronic Acids in Aqueous Media". The Journal of Organic Chemistry. 67 (8): 2721–2722. doi:10.1021/jo016342k. PMID   11950328.
3. Kuznetsov, A. G.; Korolev, D. N.; Bumagin, N. A. (2003). "Pd black in water as an efficient catalyst of the Suzuki reaction". Russian Chemical Bulletin. 52 (8): 1882–1883. doi:10.1023/A:1026097813946. S2CID   98139638.
4. "GESTIS-Stoffdatenbank". gestis.dguv.de.