General Description
Yellow solid with a slight odor. Sinks in 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 causes loss of color, nausea, headache, dizziness, drowsiness, and collapse. Eyes are irritated by liquid. Stains skin yellow; if contact is prolonged, can be absorbed into blood and cause same symptoms as for inhalation.
Fire Hazard
Behavior in Fire: May explode
Description
1,3-Dinitrobenzene (1,3-DNB) is an impurity present in the
manufacture of 2,4,6-trinitrotoluene. Workers in munitions
plants are at risk of exposure. While it does not bioaccumulate, it
persists in the environments (air, water, and soil) with slow rates
of degradation. Metabolism in animals (rabbits) results in
reduction of the nitro functionalities to amine functionalities to
produce 2,4-diaminophenol, m-nitroaniline, m-phenylenediamine,
and 2-amino-4-nitrophenol. Human exposure is generally
dermal contact or inhalation of vapor.
Chemical Properties
orange to yellow crystalline powder
Uses
Dinitrobenzene (as a mixture of 1,2-dinitro- 1,3-dinitro- and
1,4-dinitro-isomers) is used in the manufacture of dyes and
explosives, and in organic syntheses.
Uses
Organic synthesis; dyes.
Definition
ChEBI: A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.
Preparation
1,3-Dinitrobenzene is accessible by nitration of nitrobenzene. The reaction proceeds under acid catalysis using sulfuric acid. The directing effect of the nitro group of nitrobenzene leads to 93% of the product resulting from nitration at the meta-position. The ortho- and para-products occur in only 6% and 1%, respectively.
Environmental Fate
Biological. Under anaerobic and aerobic conditions using a sewage inoculum, 1,3-
dinitrobenzene degraded to nitroaniline (Hallas and Alexander, 1983). In activated sludge
inoculum, following a 20-d adaptation period, no degradation 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, 1,3-dinitrobenzene should degrade forming
identical ions.
Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and
Lewis, 1987). 1,3-Dinitrobenzene will not hydrolyze in water (Kollig, 1993).
Solubility in organics
Soluble in acetone, ether, pyrimidine (Weast, 1986), alcohol (27 g/L), pyridine (3,940 g/kg at 20–25 °C) (Dehn, 1917); freely soluble in benzene, chloroform, ethyl acetate (Windholz et al., 1983),
and toluene.
Purification Methods
Crystallise 1,3-dinitrobenzene from alkaline EtOH solution (20g in 750mL 95% EtOH at 40o, plus 100mL of 2M NaOH) by cooling and adding 2.5L of H2O. The precipitate, after filtering off, is washed with H2O, sucked dry, and crystallised from 120mL, then 80mL of absolute EtOH [Callow et al. Biochem J 32 1312 1938]. Alternatively crystallise it from MeOH, CCl4 or EtOAc. It can be sublimed in a vacuum. [Tanner J Org Chem 52 2142 1987, Beilstein 5 IV 739.]
Toxicity evaluation
Cultured astrocytes and brain capillary endothelial cells were
exposed to 1 mM concentrations for 1 day in an in vitro
blood–brain barrier (BBB) model, resulting in cell death.
