10199-87-8

Usage

Uses

Used in Dye and Pigment Manufacturing Industry:
1,3-Dinitro-2,4-diamino-benzene is used as a key intermediate in the production of various dyes and pigments. Its chemical properties allow for the creation of a wide range of colorants used in different applications, including textiles, plastics, and printing inks.
Due to the potential hazards associated with 1,3-dinitro-2,4-diamino-benzene, it is crucial to handle and store this chemical with extreme care, following strict safety protocols to minimize risks to human health and the environment.

InChI:InChI=1/C6H6N4O4/c7-3-1-2-4(9(11)12)5(8)6(3)10(13)14/h1-2H,7-8H2

Upstream product

• 73333-90-1 2,3,4-trinitro-aniline 
• 97-02-9 2,4-Dinitroanilin 
• 606-22-4 2,6-dinitroaniline 
• 74-89-5 methylamine 
• 64-17-5 ethanol 
• 7803-49-8 hydroxylamine 
• 141-52-6 sodium ethanolate 
• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 372-20-3 3-fluorophenol 
• 27684-84-0 5-bromo-2-nitrophenol 
• 99-65-0 meta-dinitrobenzene 
• 1194-66-7 2,6-dichloronitrosobenzene 
• 76361-99-4 3-bromo-2-nitro-phenol 
• 1777-85-1 acetic acid-(4-ethoxy-2,3-dinitro-anilide) 

Downstream Products

• 519-44-8 2,4-dinitroresorcinol 

Relevant academic research and scientific papers

Amination of some 1,3-dinitrobenzenes with liquid ammonia-potassium permanganate

1,3-Dinitrobenzene and some its 2- and 4-substituted derivatives are dehydroaminated in a solution of potassium permanganate in liquid ammonia to give the corresponding mono- or diamino-1,3-dinitro-benzenes. Under the same conditions, 4-fluoro-1,3-dinitrobenzene is converted into 2,4-dinitroaniline via replacement of the fluorine atom, while 2,4-dinitrobenzaldehyde gives rise to 2,4-dinitrobenzamide.

Amination of dinitrobenzenes with liquid methylamine/potassium permanganate

1,3-Dinitrobenzene (1a) and some simple monosubstituted derivatives (1b-g) were aminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to give the corresponding mono- and bis(methylamino)-substituted compounds (3a-e and 4a). 1,2-Dinitrobenzene (1i) was aminated with LMA/PP to give 2-(methylamino)-1-nitrobenzene (3f) in high yield.The intermediacy of 4-(methylamino) ?-adducts of 1,3-dinitrobenzene (2a), 2-chloro- (2b) and 2-amino-1,3-dinitrobenzene (2c) was established by 1H NMR spectroscopy.Quantum-chemical calculations for the dinitrobenzenes suggest that, in general, the experimentally observed regioselectivity of the methylamination is satisfactorily described by frontier molecular orbital (FMO) interaction of the reagents.