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.
General Description
Colorless to yellow solid. Sinks and mixes slowly with water.
Air & Water Reactions
Slowly mixes 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].
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.
Safety Profile
Suspected 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 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.]
