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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.
| Column 1 | Column 2 | Column 3 |
|---|---|---|
| Preferred IUPAC name | ||
| 1,3-Dinitrobenzene | ||
| Other names | ||
| meta-dinitrobenzene | ||
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}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/h1-4HKey: WDCYWAQPCXBPJA-UHFFFAOYSA-N | ||
| SMILES | ||
| C1=CC(=CC(=C1)N+[O-])N+[O-] | ||
| 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) | |
| 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, 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 | | |
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 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.
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.
1,3-Dinitrobenzene can be nitrated to 1,3,5-trinitrobenzene with nitronium tetrafluoroborate in fluorosulfuric acid at 150 °C.
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