Dinitrobenzene

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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. It is used as a precursor to 1,3-diaminobenzene and 3-nitroaniline. [1]

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 name 1,2-Dinitrobenzene 1,3-Dinitrobenzene 1,4-Dinitrobenzene
Other nameso-Dinitrobenzenem-Dinitrobenzenep-Dinitrobenzene
Chemical structure O-Dinitrobenzol.svg M-Dinitrobenzol.svg P-Dinitrobenzol.svg
CAS number 528-29-099-65-0100-25-4
25154-54-5 (Unspecified isomers) [2]
PubChem CID 10707 from PubChem CID 7452 from PubChem CID 7492 from PubChem
Chemical formula C6H4N2O4
Molar mass 168.11 g/mol
Magnetic Susceptibility -65.98·10−6 cm3/mol-70.53·10−6 cm3/mol-68.30·10−6 cm3/mol
Physical state solid
Appearancewhite solidyellowish solidpale yellow solid [3]
Melting point 118 °C [4] 89.6 °C [5] 174 °C [6]
Boiling point 318 °C [4] 297 °C [5] 299 °C [7]
Density 1.565 g/cm3 (17 °C) [7] 1.575 g/cm3 (18 °C) [7] 1.625 g/cm3 (18 °C) [7]
Vapor pressure 0.08 Pa (30 °C) [8] 0.07 Pa (30 °C) [8]
0.34 Pa (50 °C) [8] 0.23 Pa (50 °C) [8]
Solubility Insoluble in water
GHS hazards [9] GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
H phrases H300, H310, H330, H373, H410
P phrases P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P330, P361, P363, P391, P403+P233, P405, P501

References

  1. ↑ Booth, Gerald (2000). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_411. ISBN   978-3-527-30385-4.
  2. ↑ Recordof CAS RN 25154-54-5 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ↑ E. B. Starkey (1939). "P-DINITROBENZENE". Organic Syntheses. 19: 40. doi:10.15227/orgsyn.019.0040.
  4. 1 2 Recordof CAS RN 528-29-0 in the GESTIS Substance Database of the Institute for Occupational Safety and Health , accessed on 11 March 2008.
  5. 1 2 Recordof CAS RN 99-65-0 in the GESTIS Substance Database of the Institute for Occupational Safety and Health , accessed on 11 March 2008.
  6. ↑ Recordof CAS RN 100-25-4 in the GESTIS Substance Database of the Institute for Occupational Safety and Health , accessed on 11 March 2008.
  7. 1 2 3 4 Brockhaus ABC Chemie, VEB F.A. Brockhaus Verlag, Leipzig 1971.
  8. 1 2 3 4 Félix-Rivera, Hilsamar (2011). "Triacetone triperoxide thermogravimetric study of vapor pressure and enthalpy of sublimation in 303–338K temperature range". Thermochimica Acta. 514 (1–2): 37–43. doi:10.1016/j.tca.2010.11.034.)
  9. ↑ "Globally Harmonized System of Classification and Labelling of Chemicals (GHS)" (pdf). Geneva: United Nations. 2025. Annex 3: Codification of hazard statements, codification and use of precautionary statements, codification of hazard pictograms and examples of precautionary pictograms (pp. 293–408).
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