1,3-Dinitrobenzene Explained

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.

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]}

Notes and References

1. Book: Joachim Buddrus. Grundlagen der organischen Chemie . 3 . de Gruyter . Berlin . 2003 . 3-11-014683-5 . 360.
2. Book: Hans Beyer and Wolfgang Walter . Lehrbuch der Organischen Chemie . 19 . S. Hirzel Verlag. Stuttgart . 1981 . 3-7776-0356-2 . 536, 542.
3. Book: Michael B. . Smith . Jerry . March . March's Advanced Organic Chemistry . John Wiley & Sons . 2007 . 6th . 978-0-471-72091-1 . 688 .
4. 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 . . 1974 . 1974 . 6 . 444–445 . 10.1055/s-1974-23344 .