1,3-Dinitrobenzene

1,3-Dinitrobenzene is an organic compound with the formula C6H4(NO2)2. It is one of three isomers of dinitrobenzene. The compound is a yellow solid that is soluble in organic solvents.

1,3-Dinitrobenzene
Names
Preferred IUPAC name
1,3-Dinitrobenzene
Other names
meta-dinitrobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.524
EC Number
  • 202-776-8
RTECS number
  • CZ7350000
UNII
UN number 1597 3443
  • InChI=1S/C6H4N2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H
    Key: WDCYWAQPCXBPJA-UHFFFAOYSA-N
  • C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]
Properties
C6H4N2O4
Molar mass 168.108 g·mol−1
Appearance yellow solid
Density 1.575 g/cm3
Melting point 89.6 °C (193.3 °F; 362.8 K)
Boiling point 297 °C (567 °F; 570 K)
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H300, H310, H330, H373, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
Flash point 149 °C (300 °F; 422 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[1]

Nitration of nitrobenzene to produce dinitrobenzenes

Reactions

Reduction of 1,3-dinitrobenzene with sodium sulfide in aqueous solution leads to 3-nitroaniline. Further reduction with iron and hydrochloric acid (HCl) gives m-phenylenediamine.[2]

References
  1. Joachim Buddrus (2003). Grundlagen der organischen Chemie (3 ed.). Berlin: de Gruyter. p. 360. ISBN 3-11-014683-5.
  2. Hans Beyer and Wolfgang Walter (1981). Lehrbuch der Organischen Chemie (19 ed.). Stuttgart: S. Hirzel Verlag. pp. 536, 542. ISBN 3-7776-0356-2.
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