2,6-Xylenol

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). It is a colorless solid.

2,6-Xylenol^[1]

Names
Preferred IUPAC name 2,6-Dimethylphenol
Other names 2-Hydroxy-m-xylene
Identifiers
CAS Number	576-26-1 Y
3D model (JSmol)	Interactive image
ChemSpider	13839174 N
ECHA InfoCard	100.008.547
PubChem CID	11335
UNII	I8N0RO87OV Y
CompTox Dashboard (EPA)	DTXSID2049711 DTXSID9024063, DTXSID2049711
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	122.167 g·mol−1
Appearance	white solid
Density	1.132 g/cm3
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

Production

2,6-DMP is produced by the methylation of phenol. With production >100,000 tons/y, it is the most important xylenol. The methylation is carried out by contacting gaseous phenol and methanol at elevated temperatures in the presence of a solid acid catalyst:^[2][3]

C₆H₅OH + 2 CH₃OH → (CH₃)₂C₆H₃OH + 2 H₂O

Challenges associated with the production is the similarity of the boiling points of cresols and this xylenol.

Reactions

2,6-Xylenol is susceptible to oxidative coupling leading to polymers and dimers.^[4]

Acid-catalyzed condensation of 2,6-xylenol gives tetramethylbisphenol A. An analogue of bisphenol A, this bisphenol is used in the production of some polycarbonates. 2,6-Xylenol reacts with ammonia to give 2,6-dimethylaniline.^[2]

Toxicity

Its LD50 (oral, rats) ranges from 296-1750 mg/kg.^[2]