6219-77-8

Basic information

• Product Name: 4-nitrobenzene-1,2-diamine dihydrochloride
• Synonyms: 4-nitrobenzene-1,2-diamine dihydrochloride;4-NITRO-o-PHENYLENEDIAMINE DIHYDROCHLORIDE;1,2-Benzenediamine, 4-nitro-, dihydrochloride;2-benzenediamine, 4-nitro- dihydrochloride;4-nitro-1,2-benzenediamine dihydrochloride;Fouramine 4J;Fourrine 91;Furro 4G
• CAS NO: 6219-77-8
• Molecular Formula: C6H9Cl2N3O2
• Molecular Weight: 226.06056
• EINECS: 228-293-2
• Mol File: 6219-77-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 421.1°C at 760 mmHg
• Flash Point: 208.5°C
• Appearance: /
• Vapor Pressure: 2.68E-07mmHg at 25°C
• CAS DataBase Reference: 4-nitrobenzene-1,2-diamine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrobenzene-1,2-diamine dihydrochloride(6219-77-8)
• EPA Substance Registry System: 4-nitrobenzene-1,2-diamine dihydrochloride(6219-77-8)

Safety Data

• Hazardous Substances Data: 6219-77-8(Hazardous Substances Data)

Usage

General Description

4-nitrobenzene-1,2-diamine dihydrochloride, also known as 4-nitro-o-phenylenediamine dihydrochloride, is a chemical compound with the molecular formula C6H8N4O2·2HCl. It is a yellowish crystalline powder and is commonly used in the synthesis of dyes and pigments. The compound has potential applications in the pharmaceutical industry as well, particularly in the development of anti-cancer drugs. 4-nitrobenzene-1,2-diamine dihydrochloride also has usage in research and analytical chemistry due to its ability to react with various substances, making it useful in laboratory experiments and testing. However, it is important to handle this chemical with caution as it can be toxic when inhaled, ingested, or in contact with the skin.

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 articles and documents

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.