896-05-9

Basic information

• Product Name: 4'-(DIMETHYLAMINO)BENZYLIDENE-4-NITROANILINE
• Synonyms: 4'-(DIMETHYLAMINO)BENZAL-4-NITROANILINE;4'-(DIMETHYLAMINO)BENZYLIDENE-4-NITROANILINE;Dimethylaminobenzylidenenitroaniline
• CAS NO: 896-05-9
• Molecular Formula: C₁₅H₁₅N₃O₂
• Molecular Weight: 269.3
• Mol File: 896-05-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 451.8°C at 760 mmHg
• Flash Point: 227°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 2.37E-08mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 4'-(DIMETHYLAMINO)BENZYLIDENE-4-NITROANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-(DIMETHYLAMINO)BENZYLIDENE-4-NITROANILINE(896-05-9)
• EPA Substance Registry System: 4'-(DIMETHYLAMINO)BENZYLIDENE-4-NITROANILINE(896-05-9)

Safety Data

• Hazardous Substances Data: 896-05-9(Hazardous Substances Data)

Usage

General Description

4'-(Dimethylamino)benzylidene-4-nitroaniline is a chemical compound with the molecular formula C15H15N3O2. It is a yellow to orange crystalline solid that is commonly used as an intermediate in the synthesis of various dyes and pigments. 4'-(DIMETHYLAMINO)BENZYLIDENE-4-NITROANILINE is known for its strong absorption in the ultraviolet region, making it useful in optical and electronic applications. It is also used as a pH indicator, and as a reagent in analytic chemistry. Additionally, it has been studied for its potential use in organic light-emitting diodes due to its luminescent properties. However, it is important to handle this compound with care as it is considered harmful if swallowed, inhaled, or skin contact occurs, and may cause irritation to the eyes and skin.

InChI:InChI=1/C15H15N3O2/c1-17(2)14-7-3-12(4-8-14)11-16-13-5-9-15(10-6-13)18(19)20/h3-11H,1-2H3/b16-11+

Upstream product

• 119-58-4 4,4'-bis(dimethylamino)benzhydrol 
• 100-01-6 4-nitro-aniline 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 34025-22-4 Hexafluoraceton-N-(p-nitrophenyl)-imin 
• 7647-01-0 hydrogenchloride 
• 43001-34-9 N-(4,4'-bis-dimethylamino-benzhydryl)-4-nitro-aniline 

Downstream Products

• 279248-29-2 [(4-dimethylamino-phenyl)-(4-nitro-phenylamino)-methyl]-phosphonic acid diisopropyl ester 
• 271242-70-7 N,N-dimethyl-4-{[(4-nitrophenyl)amino]methyl}aniline 

Relevant articles and documents

Observation of the complex spectra for the supramolecular system involving silver nanoparticles-biaryl Schiff bases containing the nitro group

A series of biaryl Schiff bases containing the nitro groups, 4-XArCH═NArNO2-4′ (XBANO2-4′) and 4-NO2ArCH═NArY-4′ (4-NO2BAY), were synthesized. Also, the fish sperm DNA (fsDNA) and silver nanoparticles (AgNPs) solutions were prepared. By mixing these compounds with fsDNA or AgNPs solution and determining the ultraviolet absorption spectra of the mixture solutions, an interesting phenomenon was found: a new absorption peak λmax,lim appeared in the (XBANO2-4′)-AgNPs solution, which was longer than the wavelength of λmax of XBANO2-4′ solution. The new absorption peak in the (XBANO2-4′)-AgNPs solution was the complex spectrum originating from the electron transfer between XBANO2-4′ and AgNPs. Whereas this phenomenon was not observed in the (4-NO2BAY)-AgNPs solutions, a quantitative correlation analysis was carried out with the measured spectral data, and the results show that the wave number νmax,lim of the λmax,lim is mainly affected by the excited-state substituent constant (Formula presented.) rather than the ground Hammett constant σ of the X group. The redshift magnitude Δνmax,WSL, namely, Δνmax,WSL = (1/λmax) ? (1/λmax,lim), of the wavelength λmax,lim is related to the highest occupied molecular orbital and lowest unoccupied molecular orbital of XBANO2-4′. The discovery of this new phenomenon is helpful to understanding the interaction between AgNPs-organic compound supramolecular systems.

Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions

Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of (het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Br?nsted acid.

Synthesis of aminophosphonates with a primary amino group

Mono- and dinitro-substituted aromatic Shiff bases were reacted with diisopropyl hydrogen phosphite in the presence of the boron trifluoride-ether complex to obtain the corresponding α-aminophosphonates. Reduction of the nitro groups in the resulting phos