1,3-Dinitrobenzene

M-Dinitrobenzol.svg 124 1,3-dinitrobenzene-from-xtal-3D-bs-17.png 1,3-dinitrobenzene-from-xtal-3D-sf.png 1,3-Dinitrobenzene meta-dinitrobenzene 99-65-0 7452 7172 202-776-8 CZ7350000 1597 3443 DK8B627BU0 51397 114070 1S/C6H4N2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H WDCYWAQPCXBPJA-UHFFFAOYSA-N C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-] 6 4 2 4 yellow solid 1.575 g/cm3 89.6 297 149 06 08 09 Danger 300 310 330 373 410 260 262 264 270 271 273 280 284 301+310 302+350 304+340 310 314 320 321 322 330 361 363 391 403+233 405 501 1,3-Dinitrobenzene is one of three isomers of dinitrobenzene, with the formula C6H4(NO2)2. The compound is a yellow solid that is soluble in organic solvents.Booth Gerald Ullmann's Encyclopedia of Industrial Chemistry Nitro Compounds, Aromatic 2000 10.1002/14356007.a17_411 978-3-527-30385-4 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. Joachim Buddrus Grundlagen der organischen Chemie 3 de Gruyter Berlin 2003 3-11-014683-5 360 400px|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. Hans Beyer and Wolfgang Walter Lehrbuch der Organischen Chemie 19 S. Hirzel Verlag Stuttgart 1981 3-7776-0356-2 536, 542 1,3-Dinitrobenzene can be nitrated to 1,3,5-trinitrobenzene with nitronium tetrafluoroborate in fluorosulfuric acid at 150 °C. Michael B. Smith Jerry March March's Advanced Organic Chemistry John Wiley & Sons 2007 6th 978-0-471-72091-1 688 George A. Olah George Andrew Olah Henry C. Lin 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 1974 6 444–445 10.1055/s-1974-23344 References Category:3-Nitrophenyl compounds Category:Nitrobenzenes