General Description
Colorless to yellow solid. Sinks and mixes slowly with water.
Reactivity Profile
All 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].
Air & Water Reactions
Slowly mixes with water.
Health Hazard
INHALATION 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.
Chemical Properties
light yellow powder
Physical properties
Clear, colorless to white crystalline solid or monoclinic crystals. Slowly turns yellow on exposure
to air.
Uses
1,4-Dinitrobenzene is used in a study to evaluate the ionization mechanism and solvent effect by novel atmospheric pressure photoionization mass spectrometry in negative ion mode for analysis of some compounds. 1,4-Dinitrobenzene can be used in synthesis of dyes and dye intermediates.
Uses
manufacture of dyes, dye intermediates, explosives, plastics.
Definition
ChEBI: A dinitrobenzene carrying nitro groups at positions 1 and 4.
Environmental Fate
Biological. 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 Methods
Crystallise 1,4-dinitrobenzene from EtOH or EtOAc. Dry it under vacuum over P2O5. It can be sublimed in a vacuum. [Beilstein 5 IV 741.]
