General Description
Gray powder or dark purple solid.
Reactivity Profile
Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Air & Water Reactions
This compound is sensitive to prolonged exposure to light and air. Insoluble in water.
Health Hazard
ACUTE/CHRONIC HAZARDS: This compound is a positive animal carcinogen and suspected human carcinogen.
Fire Hazard
Flash point data for this chemical are not available; however, 4-CHLORO-M-PHENYLENEDIAMINE(5131-60-2) is probably combustible.
Chemical Properties
Crystals. Soluble in ethanol; slightly soluble in water;
insoluble in petroleum ether.
Uses
4-Chloro-1,3-diaminobenzene has been used to study the mutagenic effect of phenylenediamines hair chemicals on Salmonella typhimurium TA 102.
Uses
This compound has uses in dye production and in rubber
processing.
Definition
ChEBI: 4-Chloro-meta-phenylenediamine is a member of monochlorobenzenes.
Synthesis
General method: 2-chloro-5-nitroaniline (1 mmol), Pd/C (5% w/w) and methanol (5 mL) were mixed in a reaction vial and hydrazine hydrate (10 mmol) was added to the mixture. The reaction system was heated at reflux at 80 °C for 5 min. Upon completion of the reaction, the mixture was filtered while hot to remove the catalyst and the filtrate was concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography to give 4-chloro-1,3-benzenediamine.
References
[1] RSC Advances, 2016, vol. 6, # 23, p. 19331 - 19340
[2] Synlett, 2014, vol. 25, # 10, p. 1403 - 1408
[3] Patent: WO2006/40568, 2006, A1. Location in patent: Page/Page column 70
[4] Catalysis Communications, 2016, vol. 84, p. 25 - 29
