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2,4-Dimethylphenol

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2,4-Dimethylphenol Basic information
2,4-Dimethylphenol Chemical Properties
  • Melting point:22-23 °C(lit.)
  • Boiling point:211-212 °C(lit.)
  • Density 1.011 g/mL at 25 °C(lit.)
  • vapor pressure 0.1 mm Hg ( 25 °C)
  • refractive index n20/D 1.538(lit.)
  • Flash point:205 °F
  • storage temp. Store below +30°C.
  • solubility 5.0g/l
  • form Liquid
  • pkapK1:10.58 (25°C)
  • color Clear colorless to yellow
  • explosive limit1.4%(V)
  • Water Solubility 0.5 g/100 mL (25 ºC)
  • Merck 14,10082
  • BRN 636244
  • Henry's Law Constant42.8(x 10-6 atm?m3/mol) at 75.9 °C, 74.0 at 88.7 °C, 113.0 at 98.5 °C (VLE circulation still-UV spectrophotometry, Dohnal and Fenclová, 1995)
  • InChIKeyKUFFULVDNCHOFZ-UHFFFAOYSA-N
  • CAS DataBase Reference105-67-9(CAS DataBase Reference)
  • NIST Chemistry ReferencePhenol, 2,4-dimethyl-(105-67-9)
  • EPA Substance Registry System2,4-Dimethylphenol (105-67-9)
Safety Information
MSDS
2,4-Dimethylphenol Usage And Synthesis
  • Description2,4-dimethylphenol (also named as 2,4-xylenol) is a substituted phenol which occurs naturally. It can be also derived from the cresol fraction of petroleum or coal tars by fractional distillation and extraction with aqueous alkaline solution. It can be used as a feedstock for the production of phenolic antioxidants, disinfectants, solvents, pharmaceuticals, insecticides, fungicides, plasticizers, rubber chemicals, polyphenylene oxide, dyestuffs, wetting agents, and as an additive or constituent of gasolines, lubricants, and cresylic acid. It is an allowed liquid smoke flavoring agent in the EU.
  • Reference
    • J. P. Ghosh, K. E. Taylor, J. K. Bewtra, N. Biswas, Laccase-catalyzed removal of 2,4-dimethylphenol from synthetic wastewater: Effect of polyethylene glycol and dissolved oxygen, Chemosphere, 2008, vol. 71, pp. 1709-1717
    • G. W. Holcombe, G. L. Phipps, J. T. Fiandt, Effects of phenol, 2,4-dimethylphenol, 2,4-dichlorophenol, and pentachlorophenol on embryo, larval, and early-juvenile fathead minnows (Pimephales promelas), Archives of Environmental Contamination and Toxicology, 1982, vol. 11, pp. 73-78
    • A. Giri, Z. Zelinkova, T. Wenzl, Experimental design-based isotope-dilution SPMEGC/MS method development for the analysis of smoke flavouring products, Food Additives & Contaminants: Part A, 2007, vol. 34, pp. 2069-2084
  • Chemical Propertiesclear colorless to yellow liquid
  • Physical propertiesColorless solid, slowly turning brown on exposure to air
  • UsesDisinfectant; manufacture of pharmaceuticals, plastics, insecticides, fungicides, rubber chemicals, wetting agents, dyestuffs
  • UsesWetting agent; dyestuffs; preparation of phenolic antioxidants; plastics, resins, solvent, disinfectant, pharmaceuticals, insecticides, fungicides, and rubber chemicals manufacturing; lubricant and gasoline additive; possibly used as a pesticide; plasticizers.
  • General DescriptionColorless crystals or clear, dark amber liquid.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity Profile2,4-Dimethylphenol is a very weak acid (pKa = 10.6) . Incompatible with acid chlorides, acid anhydrides, bases and oxidizing agents. Corrodes steel, brass, copper and copper alloys .
  • Health Hazard2,4-Dimethylphenol is expected to be an irritant of the eyes, mucous membranes, and skin, by analogy to other phenols.
    The oral LD50 for rats was 3.2 g/kg; the dermal LD50 in mice was 1.04 g/kg.
  • Fire Hazard2,4-Dimethylphenol is probably combustible.
  • Safety ProfilePoison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and skin contact. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also other xylenol entries.
  • Carcinogenicity2,4-Dimethylphenol was tested for mutagenicity in the Salmonella microsome preincubation assay using the standard protocol of the National Toxicology Program and five strains of Salmonella; results were negative.
    The ACGIH has not established a threshold limit value (TLV) for 2,4-dimethylphenol.
  • SourceThomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 625. Average 2,4-dimethylphenol concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 50, 99, and 108 μg/L, respectively. 2,4-Dichlorophenol may also enter groundwater by leaching from coal tar, asphalt runoff, plastics, and pesticides (quoted, Verschueren, 1983).
  • Environmental FateBiological. When 2,4-dimethylphenol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5 and 10 mg/L, 100 and 99% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981).
    Photolytic. 2,4-Dimethylphenol absorbs UV light at a maximum wavelength of 277 nm (Dohnal and Fenclová, 1995).
    Chemical/Physical. Wet oxidation of 2,4-dimethylphenol at 320 °C yielded formic and acetic acids (Randall and Knopp, 1980). 2,4-Dimethylphenol will not hydrolyze because there is no hydrolyzable functional group (Kollig, 1993).
2,4-Dimethylphenol Preparation Products And Raw materials
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