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424625

Sigma-Aldrich

4-Phenylphenol

purified by sublimation, 99%

Synonym(s):

4-Hydroxybiphenyl

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1 G
$54.80

About This Item

Linear Formula:
C6H5C6H4OH
CAS Number:
92-69-3
Molecular Weight:
170.21
Beilstein/REAXYS Number:
1907452
EC Number:
202-179-2
MDL number:
MFCD00002347
UNSPSC Code:
12352100
PubChem Substance ID:
24866580
NACRES:
NA.22
assay:
99%

$54.80

Estimated to ship onMarch 31, 2025

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Quality Level

100

assay

99%

purified by

sublimation

bp

321 °C (lit.)

mp

164-166 °C (lit.)

solubility

water: soluble 0.7 g/L at 20 °C

functional group

phenyl

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[1] 4-arylphenol. A study on its crystalline structure has been reported.[2] Its rapid, green synthesis via a Pd(0)-catalyzed Suzuki cross-coupling reaction in water has been reported.[3] The standard molar enthalpy of formation of 4-phenylphenol has been evaluated using combustion calorimetry.[4] The solid-matrix luminescence properties for 4-phenylphenol adsorbed on filter paper has been investigated.[5] A study conducted using the yeast two-hybrid assay suggests that it shows estrogenic activity.[6]

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.[7]
  • As a starting material in the synthesis of 2,6-poly(4-phenylphenol).[8]
  • As a ligand in the synthesis of aluminum (III) bis(2-methyl-8-quninolinato)-4-phenylphenolate (BAlq).[9]

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

320.0 °F - closed cup

flash_point_c

160 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000263240
08409KE
13828BI
12025HR
06511DG

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Relationships between molecular geometry, crystal packing, and thermal motion: temperature-dependent studies of three crystal forms of 4-hydroxybiphenyl.
Brock CP and Morelan GL.
The Journal of Physical Chemistry, 90(22), 5631-5640 (1986)
" 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)
Preparation of some aryl α-L-arabinofuranosides as substrates for arabino-furanosidase.
Kelly MA, et al.
Carbohydrate Research, 181, 261-266 (1988)
The polymerization of 4-phenylphenol catalyzed by laccase.
Zhou P and Fu S.
Acta Polymerica Sinica / Gao Fen Zi Xue Bao, 4, 614-616 (2004)
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