2,6-Xylenol

2,6-Xylenol^[1]

Names
IUPAC name 2,6-Dimethylphenol
Other names 2-Hydroxy-m-xylene
Identifiers
CAS Number	576-26-1 Y
3D model (Jmol)	Interactive image
ChemSpider	13839174 N
ECHA InfoCard	100.008.547
PubChem	11335
UNII	I8N0RO87OV Y
InChI InChI=1S/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3 N Key: NXXYKOUNUYWIHA-UHFFFAOYSA-N N InChI=1/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3 Key: NXXYKOUNUYWIHA-UHFFFAOYAM
SMILES CC1=C(C(=CC=C1)C)O
Properties
Chemical formula	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 YN ?)
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).

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.^[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