4-Phenylphenol - 4-Phenylphenol

Structural formula
Structure of 4-phenylphenol
General
Name 4-Phenylphenol
other names
  • 4-Hydroxybiphenyl
  • p-Phenylphenol
  • Biphenyl-4-ol
  • 4-Biphenylol
Sum formula C12H10O
Brief description

white solid with a phenolic odor [1]

External identifiers / databases
CAS number 92-69-3
EC number 202-179-2
ECHA-InfoCard 100.001.982
PubChem 7103
Wikidata Q27116056
characteristics
Molar mass 170.21 g · mol −1 [2]
Physical state

fest

Melting point

164–166 °C[2]

boiling point

321 °C[2]

solubility
  • 50 g·l−1 in Methanol[2]
  • very sparingly soluble in water (0.7 g l −1 at 20 ° C) [1]
  • soluble in most organic solvents [3]
safety instructions
GHS hazard labeling [1]
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 315​‐​411
P: 273 [1]
Toxicological data

150 mg · kg −1 ( LD 50 , Maus , ip ) [3]

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-Phenylphenol is a colorless solid from the group of phenols .

Extraction and presentation

4-phenylphenol can be obtained by Suzuki coupling of phenylboronic acid with 4-iodophenol in the presence of 10% palladium on charcoal and potassium carbonate are obtained. [4] [5] [6]

characteristics

4-Phenylphenol is a flammable, hardly inflammable, white, flaky solid with a phenol-like odor, which is very sparingly soluble in water. [1]

use

4-Phenylphenol was used in the synthesis of a new polyphosphazene polyelectrolyte as a dispersant of single-walled carbon nanotubes in water. [2] It is also used as a stabilizer for halogenated isoprene / isobutylene rubbers. [7]

Individual evidence

  1. a b c d e Entry on 4-phenylphenol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
  2. a b c d e data sheet 4-phenylphenol, 97% from Sigma-Aldrich , accessed on June 3, 2017 ( PDF ).
  3. a b Michael Ash: Handbook of Preservatives. Synapse Info Resources, 2004, ISBN 978-1-890595-66-1, S. 489 ( limited preview in Google Book search).
  4. Brenton DeBoef: Practical Guide ( Memento of the original from September 17, 2012 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice.@1@2Vorlage:Webachiv/IABot/www.chm.uri.edu
  5. Hidehiro Sakurai, Tatsuya Tsukuda, Toshikazu Hirao: Pd/C as a Reusable Catalyst for the Coupling Reaction of Halophenols and Arylboronic Acids in Aqueous Media. In: The Journal of Organic Chemistry. 67, 2002, S. 2721, doi:10.1021/jo016342k.
  6. A. G. Kuznetsov, D. N. Korolev, N. A. Bumagin: Pd black in water as an efficient catalyst of the Suzuki reaction. In: Russian Chemical Bulletin. Band 52 , No. 8, 2003, S. 1882–1883 , doi : 10.1023 / A: 1026097813946 .
  7. Joachim Voigt: The stabilization of plastics against light and heat . Springer-Verlag, 2013, ISBN 978-3-642-52097-6 , pp. 488 ( limited preview in Google Book search).