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1,4-DINITROBENZENE

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1,4-DINITROBENZENE Basic information
1,4-DINITROBENZENE Chemical Properties
  • Melting point:170-173 °C(lit.)
  • Boiling point:183.4 °C34 mm Hg(lit.)
  • Density 1.625 g/mL at 25 °C(lit.)
  • vapor pressure 2.25 x 10-4 mmHg at 35 °C (Hine et al., 1963)
  • refractive index 1.725 (589.3 nm)
  • Flash point:150 °C
  • storage temp. 2-8°C
  • solubility alcohol: soluble1g in 300ml
  • form Crystals or Powder
  • color Ochre to orange
  • Water Solubility Soluble in water. (0.8 g/L) at 20°C.
  • Merck 14,3273
  • BRN 1105828
  • Henry's Law Constant4.79(x 10-7 atm?m3/mol) at 35 °C (approximate - calculated from water solubility and vapor pressure)
  • Exposure limitsNIOSH REL: TWA 1, IDLH 50; OSHA PEL: TWA 1 ACGIH TLV: TWA 0.15 ppm for all isomers (adopted).
  • Stability:Stable, but may be shock-sensitive. May explode if heated. Incompatible with oxidizing agents, strong bases, nitric acid, many metals, tin oxides.
  • CAS DataBase Reference100-25-4(CAS DataBase Reference)
  • EPA Substance Registry Systemp-Dinitrobenzene (100-25-4)
Safety Information
MSDS
1,4-DINITROBENZENE Usage And Synthesis
  • Chemical Propertieslight yellow powder
  • Physical propertiesClear, colorless to white crystalline solid or monoclinic crystals. Slowly turns yellow on exposure to air.
  • Usesmanufacture of dyes, dye intermediates, explosives, plastics.
  • DefinitionChEBI: A dinitrobenzene carrying nitro groups at positions 1 and 4.
  • General DescriptionColorless to yellow solid. Sinks and mixes slowly with water.
  • Air & Water ReactionsSlowly mixes with water.
  • Reactivity ProfileAll three isomers have similar properties and may react vigorously with oxidizing materials. Their reaction with nitric acid (nitration) will lead to a mixture of trinitrobenzenes possessing high-explosive properties [Urbanski, 1967, vol. 3, p. 290]. If heat and reaction conditions of the nitration are not controlled, detonation comparable to TNT may occur [Anon., J. R. Inst. Chem., 1960, 84, p. 451]. Mixture of 1,3-dinitrobenzene with tetranitromethane was found highly explosive [Urbanski, 1964, vol. 1, 592]. 1,2-dinitrobenzene is a severe explosion hazard when shocked or exposed to heat or flame. When heated to decomposition all dinitrobenzens emit toxic fumes of nitrogen oxides [Sax, 9th ed., 1996, p. 1374].
  • Health HazardINHALATION OR INGESTION: Headache, vertigo, nausea, vomiting, diarrhea, fever, rapid weak pulse, decreased blood pressure, cyanosis, exhaustion, hepatomegaly, jaundice, albuminurea, hematuria, visual scotomata, amblyopia and nystagmus. EYES: Irritation. SKIN: Stains skin yellow; if skin contact is prolonged, can be absorbed into blood causing same symptoms as for inhalation.
  • Safety ProfileSuspected carcinogen. Poison by ingestion. Mutation data reported. Mxture with nitric acid is a high explosive. When heated to decomposition it emits toxic fumes of NOx. See also 0and mDINITROBENZENE
  • Environmental FateBiological. In activated sludge inoculum, following a 20-d adaptation period, no biodegradation was observed (Pitter, 1976).
    Photolytic. 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, 1,4-dinitrobenzene should degrade forming identical ions.
    Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and Lewis, 1987). 1,4-Dinitrobenzene will not hydrolyze in water (Kollig, 1993).
  • Purification MethodsCrystallise 1,4-dinitrobenzene from EtOH or EtOAc. Dry it under vacuum over P2O5. It can be sublimed in a vacuum. [Beilstein 5 IV 741.]
1,4-DINITROBENZENE Preparation Products And Raw materials
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