ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Hydrocarbon nitrification > 1,3-Dinitrobenzene
1,3-Dinitrobenzene Chemical Properties
- Melting point:86 °C
- Boiling point:297 °C(lit.)
- Density 1.575
- vapor pressure 8.15 x 10-4 mmHg at 35 °C (Hine et al., 1963)
- refractive index 1.4660 (estimate)
- Flash point:150 °C
- storage temp. 2-8°C
- form solid
- Specific Gravity1.368
- color White to yellowish crystals
- Water Solubility 500 mg/L (20 ºC)
- Merck 14,3273
- BRN 1105654
- Exposure limitsNIOSH REL: TWA 1, IDLH 50; OSHA PEL: TWA 1; ACGIH TLV: TWA 0.15 ppm for all isomers (adopted).
- Stability:Stable. Incompatible with reducing agents, oxidizing agents, strong bases. May explode if heated.
- CAS DataBase Reference99-65-0(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzene, 1,3-dinitro-(99-65-0)
- EPA Substance Registry Systemm-Dinitrobenzene (99-65-0)
- Hazard Codes T+,N,T,F,Xn
- Risk Statements 26/27/28-33-50/53-40-36/37/38-23/24/25-11-52/53-36-20/21/22
- Safety Statements 28-36/37-45-60-61-28A-27-16-26
- RIDADR UN 3443 6.1/PG 2
- WGK Germany 3
- RTECS CZ7350000
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29042090
- Hazardous Substances Data99-65-0(Hazardous Substances Data)
- ToxicityLD50 in male, female rats (mg/kg): 91, 81 orally (Cody)
1,3-Dinitrobenzene Usage And Synthesis
- Description1,3-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 Propertiesorange to yellow crystalline powder
- UsesOrganic synthesis; dyes.
- UsesDinitrobenzene (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.
- DefinitionChEBI: A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.
- Synthesis Reference(s)The Journal of Organic Chemistry, 38, p. 4243, 1973 DOI: 10.1021/jo00964a007
Synthesis, p. 1085, 1992 DOI: 10.1055/s-1992-26309
- General DescriptionYellow solid with a slight odor. Sinks in 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 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 HazardBehavior in Fire: May explode
- Safety ProfileSuspected carcinogen. Human poison by ingestion. Experimental poison by ingestion, intraperitoneal, and intravenous routes. Human systemic effects by skin contact: cyanosis and motor activity changes. Experimental reproductive effects. An eye irritant. Mutation data reported. Mixture with nitric acid is a high explosive. Mixture with tetranitromethane is a hgh explosive very sensitive to sparks. When heated to decomposition it emits toxic fumes of NOx. See also 0and pDINITROBENZENE.
- Environmental FateBiological. 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 organicsSoluble 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 MethodsCrystallise 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 evaluationCultured 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.
1,3-Dinitrobenzene Preparation Products And Raw materials
- Preparation ProductsNitrobenzene1,3-Dichlorobenzene3-Nitroanilinem-Anisidine2,3-Dichloro-1,4-naphthoquinoneEmodin2,3,5-TRIMETHYL-1,4-BENZENE DIAMINE2-Nitrobenzenesulfenyl chloride2-Nitrobenzenesulfonamide
- Raw materialsSulfuric acid Nitric acidBenzeneSodium sulfiteSodium metabisulfiteNitrobenzeneBenzenesulfonic acid sodium salt1,4-DINITROBENZENE1,2-Dinitrobenzene
- CYCLOHEXANONE 2,4-DINITROPHENYLHYDRAZONE 2-Chloro-3,5-dinitrobenzoic acid 2,4-Dinitrofluorobenzene 2,4,7-TRINITRO-9-FLUORENONE 1,3-Difluoro-4,6-Dinitrobenzene/1,5-Difluoro-2,4-Dinitrobenzene Chlorodimethylpentafluorophenylsilane 4-CHLORO-3,5-DINITROBENZONITRILE N-(4-DIMETHYLAMINO-3,5-DINITROPHENYL)MALEIMIDE 9-DICYANOMETHYLENE-2,4,7-TRINITROFLUORENE 2-Chloro-3,5-dinitrobenzotrifluoride NAPHTHOL YELLOW S nitrazine yellow DNP 3,4-Difluoronitrobenzene 3-Bromonitrobenzene 1,4-Dinitrosobenzene 3-Nitrobenzaldehyde 3,5-Dinitrobenzoic acid