1,3-Dinitrobenzene

1,3-Dinitrobenzene is one of three isomers of dinitrobenzene, 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
CAS Number	99-65-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:51397
ChEMBL	ChEMBL114070
ChemSpider	7172
ECHA InfoCard	100.002.524
EC Number	202-776-8
PubChem CID	7452
RTECS number	CZ7350000
UNII	DK8B627BU0
UN number	1597 3443
CompTox Dashboard (EPA)	DTXSID9024065
InChI InChI=1S/C6H4N2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H Key: WDCYWAQPCXBPJA-UHFFFAOYSA-N
SMILES C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330, H373, H410
Precautionary statements	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]

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]

1,3-Dinitrobenzene can be nitrated to 1,3,5-trinitrobenzene with nitronium tetrafluoroborate in fluorosulfuric acid at 150 °C.^[3][4]

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.
3. Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. p. 688. ISBN 978-0-471-72091-1.
4. Olah, George A.; Lin, Henry C. (1974). "Synthetic Methods and Reactions; XI¹. A Convenient Direct Preparation of 1,3,5-Trinitrobenzene from m-Dinitrobenzene by Nitration with Nitronium Tetrafluoroborate in Fluorosulfuric Acid Solution". Synthesis. 1974 (6): 444–445. doi:10.1055/s-1974-23344.