309957-83-3

Basic information

• Product Name: 4-(N,N-dimethylamino)-4'-aminotriphenylmethane
• Synonyms: 4-(N,N-dimethylamino)-4'-aminotriphenylmethane
• CAS NO: 309957-83-3
• Molecular Weight: 302.419
• Mol File: 309957-83-3.mol

Chemical Properties

• CAS DataBase Reference: 4-(N,N-dimethylamino)-4'-aminotriphenylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(N,N-dimethylamino)-4'-aminotriphenylmethane(309957-83-3)
• EPA Substance Registry System: 4-(N,N-dimethylamino)-4'-aminotriphenylmethane(309957-83-3)

Safety Data

• Hazardous Substances Data: 309957-83-3(Hazardous Substances Data)

Upstream product

• 25782-57-4 (4-aminophenyl)(phenyl)methanol 
• 121-69-7 N,N-dimethyl-aniline 
• 530-44-9 4-(Dimethylamino)benzophenone 
• 5089-33-8 2-(4-bromophenyl)-1,1,1,3,3,3-hexamethyldisilazane 
• 1144-74-7 4-nitrobenzophenone 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 858788-29-1 N,N'-bis-(4-dimethylamino-benzhydryl)-urea 
• 62-53-3 aniline 

Downstream Products

• 309957-87-7 C₂₀H₁₈N₂O 
• 309957-85-5 (4-benzhydryl-2-nitro-phenyl)-dimethyl-amine 

Relevant articles and documents

Synthesis and characterization of N-demethylated metabolites of malachite green and leucomalachite green

Malachite green (MG), a triphenylmethane dye used to treat fungal and protozoan infections in fish, undergoes sequential oxidation to produce various N-demethylated derivatives (monodes-, dides(sym)-, dides(unsym)-, trides-, and tetrades-) both before and after reduction to leucomalachite green (LMG). The close structure resemblance of the metabolites with aromatic amine carcinogens implicates a potential genotoxicity from exposure to MG. The availability of the synthetic standards is important for metabolic and DNA adduct studies of MG. This paper describes a simple and versatile method for the synthesis of MG, LMG, and their N-demethylated metabolites. The synthesis involves a coupling of 4-(dimethylamino)-benzophenone or 4-nitrobenzophenone with the aryllithium reagents derived from appropriately substituted 4-bromoaniline derivatives, followed by treatment with HCl in methanol. The resulting cationic MG and their leuco analogues showed systematic UV/vis spectral and tandem mass fragmentation patterns consistent with sequential N-demethylation. The extensive 1H and 13C spectral assignments of the metabolites were aided by the availability of 13C7-labeled MG and LMG. The results indicate the existence of a resonance structure with the cationic charge located in the central methane carbon (C7). The synthetic procedure is general in scope so that it can be extended to the preparation of N-demethylated metabolites of other structurally related N-methylated triphenylmethane dyes.

Synthesis and characterization of 4'-amino and 4'-nitro derivatives of 4-N,N-dimethylaminotriphenylmethane as precursors for a proximate malachite green metabolite

This paper describes the preparation of 4'-amino (2) and 4'-nitro (3) derivatives of 4-N,N-dimethylaminotriphenylmethane as precursors for presumed DNA-binding metabolites of malachite green. The primary amine 2 was synthesized via a condensation of 4-lit