4,4'-Biphenol

4,4′-Biphenol is an organic compound which is a phenolic derivative of biphenyl. It is a colorless solid.

4,4′-Biphenol
Names
Preferred IUPAC name
[1,1′-Biphenyl]-4,4′-diol
Other names
4,4′-Dihydroxybiphenyl
4,4′-Diphenol
4,4′-Biphenyldiol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.001
EC Number
  • 202-200-5
KEGG
PubChem CID
UNII
  • InChI=1S/C12H10O2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8,13-14H Y
    Key: VCCBEIPGXKNHFW-UHFFFAOYSA-N Y
  • InChI=1/C12H10O2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8,13-14H
    Key: VCCBEIPGXKNHFW-UHFFFAOYAM
SMILES
  • Oc2ccc(c1ccc(O)cc1)cc2
Properties
C12H10O2
Molar mass 186.210 g·mol−1
Appearance colorless or white solid
Melting point 283 °C (541 °F; 556 K)
Boiling point Sublimes
Insoluble in water
Soluble in ethanol and ether
Hazards
Flash point > 93.3 °C (199.9 °F; 366.4 K)
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

4,4′-Biphenol is prepared by dealkylation of the tetra-t-butyl derivative, generated by the oxidative coupling of 2,6-di-tert-butylphenol. The oxidative coupling of phenol itself typically gives a mixture of isomers. For example, VCl4 reacts with phenols give 4,4′-, 2,4′-, and 2,2′-biphenols:

2 C6H5OH + 2 VCl4 → HOC6H4–C6H4OH + 2 VCl3 + 2 HCl

An earlier process using oxygen and copper salts to enable the oxidative coupling was reported

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