1,3-Dinitrobenzene

1,3-Dinitrobenzene is one of three isomers of dinitrobenzene, with the formula C₆H₄₂. It is one of three isomers of dinitrobenzene. The compound is a yellow solid that is soluble in organic solvents.

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.

Reactions

Reduction of 1,3-dinitrobenzene with sodium sulfide in aqueous solution leads to 3-nitroaniline. Further reduction with iron and hydrochloric acid gives m-phenylenediamine.
1,3-Dinitrobenzene can be nitrated to 1,3,5-trinitrobenzene with nitronium tetrafluoroborate in fluorosulfuric acid at 150 °C.