Dinitrobenzene Explained

Dinitrobenzenes are nitrobenzenes composed of a benzene ring and two nitro group (-NO2) substituents. The three possible arrangements of the nitro groups afford three isomers, 1,2-dinitrobenzene, 1,3-dinitrobenzene, and 1,4-dinitrobenzene. Each isomer has the chemical formula C6H4N2O4 and a molar mass of about 168.11 g/mol. 1,3-Dinitrobenzene is the most common isomer and it is used in the manufacture of explosives.

Properties

The dinitrobenzenes are all crystalline solids. The boiling points of the three isomers are relatively close; however, the melting points significantly differ. 1,4-Dinitrobenzene, which has the highest symmetry, has the highest melting point.

Dinitrobenzenes
IUPAC name1,4-Dinitrobenzene
Other nameso-Dinitrobenzene m-Dinitrobenzene p-Dinitrobenzene
Chemical structure
CAS number528-29-0 99-65-0 100-25-4
25154-54-5 (Unspecified isomers)
PubChem
Chemical formulaC6H4N2O4
Molar mass168.11 g/mol
Magnetic Susceptibility-65.98·10−6 cm3/mol-70.53·10−6 cm3/mol-68.30·10−6 cm3/mol
Physical statesolid
Appearancewhite solidyellowish solidpale yellow solid[1]
Melting point118 °C89.6 °C174 °C
Boiling point318 °C297 °C299 °C[2]
Density1.565 g/cm3 (17 °C) 1.575 g/cm3 (18 °C) 1.625 g/cm3 (18 °C)
Vapor pressure0.08 Pa (30 °C)[3] 0.07 Pa (30 °C)
0.34 Pa (50 °C)0.23 Pa (50 °C)
SolubilityInsoluble in water
GHS hazards
H phrases
P phrases

Notes and References

  1. E. B. Starkey . P-DINITROBENZENE . Organic Syntheses . 1939 . 19 . 40 . 10.15227/orgsyn.019.0040.
  2. Brockhaus ABC Chemie, VEB F.A. Brockhaus Verlag, Leipzig 1971.
  3. 10.1016/j.tca.2010.11.034 . Triacetone triperoxide thermogravimetric study of vapor pressure and enthalpy of sublimation in 303–338K temperature range . Thermochimica Acta . 2011 . 514 . 1–2 . 37–43 . Hilsamar . Félix-Rivera.)