6219-77-8

Usage

Uses

Used in Dye and Pigment Synthesis:
4-nitrobenzene-1,2-diamine dihydrochloride is used as a key intermediate in the production of dyes and pigments for various applications, including textiles, plastics, and printing inks. Its chemical structure allows for the creation of a wide range of colorants with different properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-nitrobenzene-1,2-diamine dihydrochloride is used as a precursor in the development of anti-cancer drugs. Its chemical properties make it a candidate for the synthesis of compounds that can target and treat cancer cells.
Used in Research and Analytical Chemistry:
4-nitrobenzene-1,2-diamine dihydrochloride is used as a reagent in research and analytical chemistry due to its ability to react with a variety of substances. This makes it useful for conducting laboratory experiments and testing, where its reactivity can be harnessed to detect or measure the presence of other compounds.
Used in Laboratory Experiments:
4-nitrobenzene-1,2-diamine dihydrochloride is used as a reactant in laboratory experiments to explore its chemical properties and potential applications. Its reactivity with different substances can lead to the discovery of new chemical reactions and the development of novel compounds.
Used in Testing Procedures:
In testing procedures, 4-nitrobenzene-1,2-diamine dihydrochloride is used to validate the presence or properties of other chemicals. Its interaction with various substances can help in the qualitative and quantitative analysis of samples in a laboratory setting.

InChI:InChI=1/C6H7N3O2.2ClH/c7-5-2-1-4(9(10)11)3-6(5)8;;/h1-3H,7-8H2;2*1H

Upstream product

• 99-56-9 4-Nitrophenylene-1,2-diamine 

Relevant academic research and scientific papers

Hydrogen bonding in 4-nitrobenzene-1,2-diamine and two hydrohalide salts

The structures of 4-nitrobenzene-1,2-diamine [C6H 7N3O2, (I)], 2-amino-5-nitroanilinium chloride [C6H8N3O2+ Cl -, (II)] and 2-amino-5-nitroanilinium bromide monohydrate [C 6H8N3O2+ Br- H2O, (III)] are reported and their hydrogen-bonded structures described. The amine group para to the nitro group in (I) adopts an approximately planar geometry, whereas the meta amine group is decidedly pyramidal. In the hydrogen halide salts (II) and (III), the amine group meta to the nitro group is protonated. Compound (I) displays a pleated-sheet hydrogen-bonded two-dimensional structure with R22(14) and R44(20) rings. The sheets are joined by additional hydrogen bonds, resulting in a three-dimensional extended structure. Hydrohalide salt (II) has two formula units in the asymmetric unit that are related by a pseudo-inversion center. The dominant hydrogen-bonding interactions involve the chloride ion and result in R42(8) rings linked to form a ladder-chain structure. The chains are joined by N-H...Cl and N-H...O hydrogen bonds to form sheets parallel to (010). In hydrated hydrohalide salt (III), bromide ions are hydrogen bonded to amine and ammonium groups to form R 42(8) rings. The water behaves as a double donor/single acceptor and, along with the bromide anions, forms hydrogen bonds involving the nitro, amine, and ammonium groups. The result is sheets parallel to (001) composed of alternating R55(15) and R64(24) rings. Ammonium N-H...Br interactions join the sheets to form a three-dimensional extended structure. Energy-minimized structures obtained using DFT and MP2 calculations are consistent with the solid-state structures. Consistent with (II) and (III), calculations show that protonation of the amine group meta to the nitro group results in a structure that is about 1.5 kJ mol-1 more stable than that obtained by protonation of the para-amine group. DFT calculations on single molecules and hydrogen-bonded pairs of molecules based on structural results obtained for (I) and for 3-nitrobenzene-1,2-diamine, (IV) [Betz & Gerber (2011). Acta Cryst. E67, o1359] were used to estimate the strength of the N-H...O(nitro) interactions for three observed motifs. The hydrogen-bonding interaction between the pairs of molecules examined was found to correspond to 20-30 kJ mol -1.