75113-69-8

Basic information

• Product Name: N,N-di-n-butyl-2,4-dinitroaniline
• Synonyms: N,N-di-n-butyl-2,4-dinitroaniline
• CAS NO: 75113-69-8
• Molecular Weight: 295.338
• Mol File: 75113-69-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N,N-di-n-butyl-2,4-dinitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-di-n-butyl-2,4-dinitroaniline(75113-69-8)
• EPA Substance Registry System: N,N-di-n-butyl-2,4-dinitroaniline(75113-69-8)

Safety Data

• Hazardous Substances Data: 75113-69-8(Hazardous Substances Data)

Upstream product

• 70-34-8 2,4-Dinitrofluorobenzene 
• 111-92-2 dibutylamine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 584-48-5 2,4-dinitrobromobenzene 
• 102-82-9 tributyl-amine 
• 613-29-6 N-Dibutylaniline 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 

Relevant articles and documents

A probable hydrogen-bonded meisenheimer complex: An unusually high S NAr reactivity of nitroaniline derivatives with hydroxide ion in aqueous media

Observations show that nitroanilines exhibit an unusually high S NAr reactivity with OH- in aqueous media in reactions that produce nitrophenols. SNAr reaction of 4-nitroaniline (2a) in aqueous NaOH for 16 h yields 4-nitrophenol (4a) quantitatively, whereas a similar reaction of 4-nitrochlorobenzene (1a) gave 4a in 2% yield together with recovered 1a in 97%, suggesting that the leaving ability of the NH2 group far surpasses that of Cl under these conditions. An essential feature of SNAr reactions of nitroanilines is probably that the NH2 leaving group participates in a hydrogen-bonding interaction with H 2O. Density functional theory (DFT) calculations for a set of 4-nitroaniline, OH-, and H2O suggest a possible formation of a Meisenheimer complex stabilized by hydrogen-bonding interactions and a six-membered ring structure. The results obtained here contrast with conventional SNAr reactivity profiles in which nitroanilines are nearly unreactive with nucleophiles in organic solvents.

Photoredox catalyzed dealkylative aromatic halogen substitution with tertiary amines

A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are

REACTIONS OF SUBSTITUTED HALOGENOBENZENES WITH TRIBUTYLAMINE

The reactions of 2,4-dinitrohalobenzenes and 2-nitro-4-trifluoromethylsulfonylchlorobenzene with tributylamine in DMFA lead to the formation of two products, i.e., substituted N,N-dibutylanilines and phenols.The reactions occur with an induction period, which disappears with increase in temperature, and with fractional orders in the reagents.The effective activation was determined by means of the transformation coefficients.The ordes of mobility of the halogens in the reaction of 2,4-dinitrohalogenobenzenes with tributylamine is Br >= Cl > F.The effect of substituents on the mobility of the chlorine corresponds to their accepting characteristics: SO2CF3 > NO2.