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424625

Sigma-Aldrich

4-Phenylphenol

purified by sublimation, 99%

Synonym(s):

4-Hydroxybiphenyl

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About This Item

Linear Formula:
C6H5C6H4OH
CAS Number:
92-69-3
Molecular Weight:
170.21
Beilstein:
1907452
EC Number:
202-179-2
MDL number:
MFCD00002347
UNSPSC Code:
12352100
PubChem Substance ID:
24866580
NACRES:
NA.22

Assay

99%

purified by

sublimation

bp

321 °C (lit.)

mp

164-166 °C (lit.)

solubility

water: soluble 0.7 g/L at 20 °C

SMILES string

Oc1ccc(cc1)-c2ccccc2

InChI

1S/C12H10O/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13H

InChI key

YXVFYQXJAXKLAK-UHFFFAOYSA-N

Gene Information

rat ... Ar(24208)

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General description

4-Phenylphenol (4-hydroxybiphenyl, 4-HBP), a biaryl compound, is a weakly acidic 4-arylphenol. A study on its crystalline structure has been reported. Its rapid, green synthesis via a Pd(0)-catalyzed Suzuki cross-coupling reaction in water has been reported. The standard molar enthalpy of formation of 4-phenylphenol has been evaluated using combustion calorimetry. The solid-matrix luminescence properties for 4-phenylphenol adsorbed on filter paper has been investigated. A study conducted using the yeast two-hybrid assay suggests that it shows estrogenic activity.

Application

4-Phenylphenol may be used in the following studies:
  • As a reactant in the synthesis of new azobenzene sulfonic acid dopants by diazotized coupling reaction with sulphanilic acid diazonium salt.
  • As a starting material in the synthesis of 2,6-poly(4-phenylphenol).
  • As a ligand in the synthesis of aluminum (III) bis(2-methyl-8-quninolinato)-4-phenylphenolate (BAlq).

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315,H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Irrit. 2 - Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

320.0 °F - closed cup

Flash Point(C)

160 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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" Greening Up" the Suzuki Reaction.
Aktoudianakis E, et al.
Journal of Chemical Education, 85(4), 555-555 (2008)
Thermochemistry of phenols: experimental standard molar enthalpies of formation of 2-phenylphenol, 4-phenylphenol, 2, 6-diphenylphenol, and 2, 2'-and 4, 4'-dihydroxybiphenyl.
Verevkin SP.
The Journal of Chemical Thermodynamics, 30(3), 389-396 (1998)
Yuko Ogawa et al.
Food additives and contaminants, 23(4), 422-430 (2006-03-21)
Food contact plastics and rubbers possibly contain many kinds of chemicals such as monomers, oligomers, additives, degradation products of polymers and additives, and impurities. Among them, bisphenol A, nonylphenol, benzylbutyl phthalate, styrene oligomers and hydroxylated benzophenones have been reported to
Characterization of electronic structure of aluminum (III) bis (2-methyl-8-quninolinato)-4-phenylphenolate (BAlq) for phosphorescent organic light emitting devices.
Chu TY, et al.
Chemical Physics Letters, 404(1), 121-125 (2005)
Synthesis and characterization of new azobenzenesulfonic acids doped conducting polyaniline.
Jayakannan M, et al.
Eur. Polymer J., 42(10), 2623-2631 (2006)
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