2,6-Xylenol

2,6-Xylenol[1]
2,6-Xylenol molecule
Names
IUPAC name
2,6-Dimethylphenol
Other names
2-Hydroxy-m-xylene
Identifiers
576-26-1 YesY
ChemSpider 13839174 N
Jmol interactive 3D Image
PubChem 11335
UNII I8N0RO87OV YesY
Properties
C8H10O
Molar mass 122.17 g·mol−1
Melting point 43 to 45 °C (109 to 113 °F; 316 to 318 K)
Boiling point 203 °C (397 °F; 476 K)
Hazards
Flash point 86 °C (187 °F; 359 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

2,6-Xylenol is a chemical compound which is one of the six isomers of xylenol. It is also commonly known as 2,6-dimethylphenol (DMP).

2,6-Xylenol is a monomer for poly(p-phenylene oxide) engineering resins through carbon - oxygen oxidative coupling. Carbon to carbon dimerization is also possible. In one study 2,6-xylenol is oxidized with iodosobenzene diacetate with an 5 fold excess of the phenol.[2]

In the first step of the proposed reaction mechanism the acetyl groups in the iodine compound are replaced with the phenol. This complex dissociates into an aryl radical anion and a phenoxy residue. The two aryl radicals recombine forming a new carbon carbon covalent bond and subsequently lose two protons in a rearomatization step. The immediate reaction product is a diphenoquinone as result of a one-step 4-electron oxidation. It is nevertheless possible to synthesize the biphenol compound via a comproportionation of the quinone with xylenol already present. In this reaction sequence the hypervalent iodine reagent is eventually reduced to phenyliodine.

References

  1. 2,6-Xylenol at Sigma-Aldrich
  2. Selective oxidative para C–C dimerization of 2,6-dimethylphenol Christophe Boldron, Guillem Aromí, Ger Challa, Patrick Gamez and Jan Reedijk Chemical Communications, 2005, (46), 5808 - 5810 Abstract


This article is issued from Wikipedia - version of the Monday, November 02, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.