1,3-Dinitrobenzene is one of three

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

s of

dinitrobenzene Dinitrobenzenes are nitrobenzenes composed of a benzene ring and two nitro group (-NO2) substituents. The three possible arrangements of the nitro groups afford three isomers, 1,2-dinitrobenzene, 1,3-dinitrobenzene, and 1,4-dinitrobenzene. Each iso ...

, with the formula C₆H₄(NO₂)₂. It is one of three

s of

. The compound is a yellow solid that is soluble in organic solvents.

Preparation

1,3-Dinitrobenzene is accessible by

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...

nitrobenzene Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5 NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced ...

. The reaction proceeds under

acid catalysis In acid catalysis and base catalysis, a chemical reaction is catalyzed by an acid or a base. By Brønsted–Lowry acid–base theory, the acid is the proton (hydrogen ion, H+) donor and the base is the proton acceptor. Typical reactions catalyz ...

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. : Nitration2

Reactions

Reduction of 1,3-dinitrobenzene with

sodium sulfide Sodium sulfide is a chemical compound with the formula Na2 S, or more commonly its hydrate Na2S·9 H2O. Both the anhydrous and the hydrated salts are colorless solids, although technical grades of sodium sulfide are generally yellow to brick red ...

in aqueous solution leads to

3-nitroaniline 3-Nitroaniline is an organic compound with the formula H2NC6H4NO2. A yellow solid, it is a derivative of aniline, carrying a nitro functional group in position 3. It is an isomer of 2-nitroaniline and 4-nitroaniline. It is used as a precursor t ...

. Further reduction with

iron Iron is a chemical element; it has symbol Fe () and atomic number 26. It is a metal that belongs to the first transition series and group 8 of the periodic table. It is, by mass, the most common element on Earth, forming much of Earth's o ...

and

hydrochloric acid Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...

(HCl) gives m-phenylenediamine. 1,3-Dinitrobenzene can be nitrated to

1,3,5-trinitrobenzene 1,3,5-Trinitrobenzene is one of three isomers of trinitrobenzene with the formula C6H3(NO2)3. A pale yellow solid, the compound is highly explosive. Synthesis and reactions 1,3,5-Trinitrobenzene is produced by decarboxylation of 2,4,6-trinitrob ...

with

nitronium tetrafluoroborate Nitronium tetrafluoroborate is an inorganic compound with formula NO2BF4. It is a salt of nitronium cation and tetrafluoroborate anion. It is a colorless crystalline solid, which reacts with water to form the corrosive acids HF and HNO3. As su ...

fluorosulfuric acid Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula . It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, , substitu ...

at 150 °C.

References

{{DEFAULTSORT:Dinitrobenzene, 1,3- Nitrobenzenes