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2,6-Dinitrotoluene Basic information
2,6-Dinitrotoluene Chemical Properties
  • Melting point:56-61 °C(lit.)
  • Boiling point:300°C
  • Density 1.2833
  • vapor pressure 3.5(x 10-4 mmHg) at 20 °C (quoted, Howard, 1989)5.67(x 10-4 mmHg) at 25 °C (Banerjee et al., 1990)
  • refractive index 1.4790
  • Flash point:207°C
  • storage temp. 2-8°C
  • solubility Soluble in ethanol (Weast, 1986) and many other organic solvents including chloroform and carbon tetrachloride.
  • Water Solubility 0.0182 g/100 mL
  • BRN 2052046
  • Stability:Stable, but shock sensitive. Incompatible with oxidizing agents, reducing agents, strong bases. Heating may cause explosion.
  • CAS DataBase Reference606-20-2(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzene, 2-methyl-1,3-dinitro-(606-20-2)
  • EPA Substance Registry System2,6-Dinitrotoluene (606-20-2)
Safety Information
2,6-Dinitrotoluene Usage And Synthesis
  • Chemical Propertiestan crystals
  • Physical propertiesPale yellow, orange, brown or reddish rhombic crystals. Odor threshold concentration in water is 100 ppb (quoted, Keith and Walters, 1992).
  • UsesOrganic synthesis; propellant additive; manufacture of explosives; intermediate in the manufacture of polyurethanes.
  • Uses2,6-Dinitrotoluene is used primarily, along with the other isomers, in producing toluene diisocyanate; production of the diisocyanate ranges from 100 million to almost a billion pounds each year.
  • DefinitionChEBI: A dinitrotoluene carrying nitro substituents at positions 2 and 6.
  • General DescriptionYellow to red solid or heated liquid with a slight odor. Solidifies in cool water. Solid and liquid sink in water.
  • Air & Water ReactionsMixes slowly with water. Insoluble in water.
  • Reactivity Profile2,6-Dinitrotoluene is sensitive to heat. 2,6-Dinitrotoluene may explode when exposed to heat or flame. 2,6-Dinitrotoluene can be detonated only by a very strong initiator. 2,6-Dinitrotoluene is incompatible with strong oxidizers. 2,6-Dinitrotoluene is also incompatible with caustics and metals such as tin and zinc. 2,6-Dinitrotoluene may react with reducing agents. 2,6-Dinitrotoluene will attack some forms of plastics, rubber and coatings.
  • Health HazardINHALATION, INGESTION OR SKIN ABSORPTION: Headache, weakness, nausea or dizziness, cyanosis, drowsiness, shortness of breath and collapse. Can burn eyes and skin.
  • Safety ProfilePoison by ingestion. A skin irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also 2,4-DINITROTOLUENE
  • Environmental FateBiological. When 2,6-dinitrotoluene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with gradual acclimation was followed by deadaptive process in subsequent subcultures. At a concentration of 5 mg/L, 82, 55, 47, and 29% losses were observed after 7, 14, 21, and 28-d incubation periods, respectively. At a concentration of 10 mg/L, only 57, 49, 35, and 13% were observed after 7, 14, 21, and 28-d incubation periods, respectively (Tabak et al., 1981). Under anaerobic and aerobic conditions, a sewage inoculum degraded 2,6-dinitrotoluene to aminonitrotoluene (Hallas and Alexander, 1983).
    Photolytic. Simmons and Zepp (1986) estimated the photolytic half-life of 2,6-dinitrotoluene in surface water to range from 2 to 17 h.
    Low et al. (1991) reported that the nitro-containing compounds (e.g., 2,4-dinitrophenol) undergo degradation by UV light in the presence of titanium dioxide yielding ammonium, carbonate, and nitrate ions. By analogy, 2,6-dinitrotoluene should degrade forming identical ions.
    Chemical/Physical. 2,6-Dinitrotoluene will not hydrolyze (Kollig, 1993).
    At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 145, 70, 33, and 16 mg/g, respectively (Dobbs and Cohen, 1980).
  • Metabolic pathway2-Amino-6-nitrotoluene, 2,6-dinitrobenzyl alcohol, 2- amino-6-nitrobenzyl alcohol, and the conjugates of the latter two alcohols are detected in the urine of male Wistar rats as metabolites of 2,6-dinitrotoluene (2,6- DNT). In addition to the metabolites identified in the urine, 2,6-dinitrobenzaldehyde is detected in the rat bile. Incubation of 2,6-DNT with a hepatic microsomal preparation gives 2,6-dinitrobenzyl alcohol. Incubation of benzyl alcohol with a microsomal plus cytosol preparation gives 2,6-dinitrobenzaldehyde, and incubation of 2,6-dinitrobenzaldehyde with cytosol preparations gives 2,6-dinitrobenzyl alcohol and 2,6- dinitrobenzoic acid.
  • Purification MethodsCrystallise it from acetone. EXPLOSIVE when dry.[Beilstein 5 III 761, 5 IV 866.]
2,6-Dinitrotoluene Preparation Products And Raw materials
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