1,3-Dinitrobenzene

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1,3-Dinitrobenzene
M-Dinitrobenzol.svg
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
Properties
C6H4N2O4
Molar mass 168.11 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 pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H300, H310, H330, H373, H400, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P304+340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+233, P405, P501
Flash point 149°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

Preparation[edit]

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[edit]

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[edit]

  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.