1,3-Dinitrobenzene Chemical Properties
- Melting point:
- 86 °C
- Boiling point:
- 297 °C(lit.)
- 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.
- White to yellowish crystals
- Specific Gravity
- Water Solubility
- 500 mg/L (20 ºC)
- Exposure limits
- NIOSH REL: TWA 1, IDLH 50; OSHA PEL: TWA 1; ACGIH TLV: TWA 0.15 ppm for all isomers (adopted).
- Stable. Incompatible with reducing agents, oxidizing agents, strong bases. May explode if heated.
- CAS DataBase Reference
- 99-65-0(CAS DataBase Reference)
- NIST Chemistry Reference
- Benzene, 1,3-dinitro-(99-65-0)
- EPA Substance Registry System
- m-Dinitrobenzene (99-65-0)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 3443 6.1/PG 2
- WGK Germany
- HS Code
- Hazardous Substances Data
- 99-65-0(Hazardous Substances Data)
- LD50 in male, female rats (mg/kg): 91, 81 orally (Cody)
1,3-Dinitrobenzene Usage And Synthesis
orange to yellow crystalline powder
Organic synthesis; dyes.
ChEBI: A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.
The Journal of Organic Chemistry, 38, p. 4243, 1973 DOI: 10.1021/jo00964a007
Synthesis, p. 1085, 1992
Yellow solid with a slight odor. Sinks in water.
Air & Water Reactions
Slowly mixes with water.
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].
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.
Behavior in Fire: May explode
Suspected 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.
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.
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.]
1,3-Dinitrobenzene Preparation Products And Raw materials
- NAPHTHOL YELLOW S
- nitrazine yellow
- 1,4-DINITROBENZENE OEKANAL, 250 MG,1,4-Dinitrobenzene, 98+%,1,4-DINITROBENZENE, 1X1ML, MEOH, 2000UG/ ML,1,4-DINITROBENZENE, 1000MG, NEAT
- 1,2-DINITROBENZENE, 99+%,1,2-DINITROBENZENE OEKANAL, 250 MG
- 3,5-Dinitrobenzoic acid
- Sodium 3-nitrobenzenesulphonate