2,6-Xylenol
Names | |
---|---|
Preferred IUPAC name
2,6-Dimethylphenol | |
Other names
2-Hydroxy-m-xylene
| |
Identifiers | |
3D model (JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.008.547 |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C8H10O | |
Molar mass | 122.167 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).
|
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).
A known application of DMP is in the synthesis of Mexiletine.
Production
2,6-DMP can be produced by the direct methylation of phenol. This is carried out with gaseous phenol and methanol at elevated temperatures in the presence of a catalyst[2]
Related polymers
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 a fivefold excess of the phenol.[3]
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
- ^ 2,6-Xylenol at Sigma-Aldrich
- ^ Zukowski, W.; Berkowicz, G.; Baron, J.; Kandefer, S.; Jamanek, D.; Szarlik, S.; Wielgosz, Z.; Zielecka, M. (2014). "Selective phenol methylation to 2,6-dimethylphenol in a fluidized bed of iron-chromium mixed oxide catalyst with o-cresol circulation" (PDF). Chemistry Central Journal. 8 (1): 51. doi:10.1186/s13065-014-0051-6. PMC 4172955. PMID 25342964.
{{cite journal}}
: CS1 maint: unflagged free DOI (link) - ^ 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