:2,6-Xylenol
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477212188
| Reference =[http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=W324906|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 2,6-Xylenol] at Sigma-Aldrich
| ImageFile = 2,6-Xylenol.svg
| ImageSize = 180px
| ImageFile1 = 2,6-Xylenol-3D-spacefill.png
| ImageSize1 = 160
| ImageAlt1 = 2,6-Xylenol molecule
| PIN = 2,6-Dimethylphenol
| OtherNames = 2-Hydroxy-m-xylene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 576-26-1
| PubChem = 11335
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = I8N0RO87OV
| SMILES = CC1=C(C(=CC=C1)C)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 13839174
| InChI = 1/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3
| InChIKey = NXXYKOUNUYWIHA-UHFFFAOYAM
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NXXYKOUNUYWIHA-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=8 | H=10 | O=1
| Appearance = white solid
| Density = 1.132 g/cm3
| MeltingPtC = 43 to 45
| MeltingPt_notes =
| BoilingPtC = 203
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 86
| AutoignitionPtC =
}}
}}
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.
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:{{cite book |doi=10.1002/14356007.a08_025|chapter=Cresols and Xylenols |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2000 |last1=Fiege |first1=Helmut |isbn=3527306730 }}{{cite journal|pmid=25342964|pmc=4172955|year=2014|last1=Zukowski|first1=W.|title=Selective phenol methylation to 2,6-dimethylphenol in a fluidized bed of iron-chromium mixed oxide catalyst with o-cresol circulation|journal=Chemistry Central Journal|volume=8|issue=1|pages=51|last2=Berkowicz|first2=G.|last3=Baron|first3=J.|last4=Kandefer|first4=S.|last5=Jamanek|first5=D.|last6=Szarlik|first6=S.|last7=Wielgosz|first7=Z.|last8=Zielecka|first8=M.|doi=10.1186/s13065-014-0051-6|url=https://core.ac.uk/download/pdf/81194098.pdf |doi-access=free }}
:{{chem2|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.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 [http://www.rsc.org/publishing/journals/CC/article.asp?doi=b510378a Abstract]
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.
Toxicity
Its LD50 (oral, rats) ranges from 296-1750 mg/kg.