539-17-3

Usage

Uses

Used in Textile Industry:
N,N-DIMETHYL-4,4'-AZODIANILINE is used as a dye for coloring synthetic fibers, particularly polyamides. It provides excellent ironing fastness, light fastness, perspiration fastness, and washing fastness, as indicated by its ISO ratings of 2, 3, 4, and 3-4, respectively.
Used in Solvent Industry:
N,N-DIMETHYL-4,4'-AZODIANILINE is used as a component in the formulation of solvents due to its solubility in various mediums such as ethanol, acetone, and carbon tetrachloride.
Used in Pottery Industry:
N,N-DIMETHYL-4,4'-AZODIANILINE is utilized as a coloring agent in the pottery industry, where it imparts a distinctive black, red, and black-red crystallization to the finished products.
Used in Dyes and Metabolites:
N,N-DIMETHYL-4,4'-AZODIANILINE is also employed in the production of other dyes and metabolites, contributing to the diversity of color options available in various industries.

Preparation

4-Nitrobenzenamine diazo, and N,N-dimethylaniline?coupling, and then will the nitro reductive into amino.

Safety Profile

Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx

Fading

Stain

Purification Methods

Crystallise the azo-dye from aqueous EtOH. [Beilstein 14 IV 1004.]

InChI:InChI=1/C14H16N4/c1-18(2)14-9-7-13(8-10-14)17-16-12-5-3-11(15)4-6-12/h3-10H,15H2,1-2H3

Upstream product

• 2491-74-9 N,N-dimethyl-4-(4-nitrophenylazo)aniline 
• 1591-56-6 acetic acid-[4-(4-dimethylamino-phenylazo)-anilide] 
• 138-89-6 p-dimethylaminonitrosobenzene 
• 106-50-3 1,4-phenylenediamine 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 100-01-6 4-nitro-aniline 
• 99-98-9 4-amino-N,N-dimethylaniline 

Downstream Products

• 1591-56-6 acetic acid-[4-(4-dimethylamino-phenylazo)-anilide] 
• 79307-81-6 chloro-acetic acid-[4-(4-dimethylamino-phenylazo)-anilide] 
• 6257-64-3 methyl orange 
• 81530-90-7 (N_.N-Dimethyl-anilin)-(4 azo 1)-benzol-(4 azo 4)-phenol 
• 83922-67-2 4-octanoylamino-4'-(dimethylamino)azobenzene 
• 119428-84-1 1,4-Diamino-2-chloro-3-[4-(4-dimethylamino-phenylazo)-phenylamino]-anthraquinone 
• 69074-65-3 4-{[(E)-4-(4-Dimethylamino-phenylazo)-phenylimino]-methyl}-benzonitrile 
• 42985-83-1 2-[1-[4-(4-Dimethylamino-phenylazo)-phenylamino]-meth-(Z)-ylidene]-3,4-dihydro-2H-naphthalen-1-one 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 1229570-64-2 C₂₁H₂₇N₉S₂ 
• 1338925-82-8 C₂₇H₂₄N₄ 
• 106-50-3 1,4-phenylenediamine 
• 1393659-21-6 2,6-bis(4-[2-(4-(dimethylamino)phenyl)diazen-1-yl]phenyl)-1H,2H,3H,5H,6H,7H-pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone 
• 87963-80-2 1-(4-[2-(4-(dimethylamino)phenyl)diazen-1-yl]phenyl)-2,5-dihydro-1H-pyrrole-2,5-dione 

Relevant academic research and scientific papers

Azo aryl urea derivative, and preparation method and application thereof

The invention relates to an azo aryl urea derivative, and a preparation and an application thereof, and concretely discloses a compound represented by formula (I), or an optical isomer, a cis-trans-isomer or a pharmaceutically acceptable salt thereof, and a preparation method thereof. Definitions of substituent groups in the general formula are described in the specification and claims. The invention further discloses a composition containing the above compound, and an application thereof. The compound has excellent anticancer activity on HepG2 liver cancer cells, MGC803 gastric cancer cells,HCT116 colon cancer and the like.

Molecular length adjustment for organic azo-based nonvolatile ternary memory devices

Two conjugated small molecules with different molecular length, DPAPIT and DPAPPD, in which an electron donor dimethylamino moiety and an electron acceptor phthalimide core unit are bridged by another electron-accepting azobenzene block, were designed and synthesized. DPAPIT molecule with longer conjugation length stacked regularly in the solid state and formed uniform nanocrystalline film. The fabricated memory devices with DPAPIT as active material exhibited outstanding nonvolatile ternary memory effect with the current ratio of ～1:101.7:104 for "0", "1" and "2" states and all the switching threshold voltages lower than -3 V. In contrast, the shorter molecule DPAPPD showed amorphous microstructure and no obvious conductive switching behavior was observed in the device. The crystallinity and surface roughness of DPAPIT thin films were significantly improved as the annealing temperature increased, lowering the switching threshold voltages which are highly desirable for low-power consumption data-storage devices. It is worth noting that the tristable memory signals of DPAPIT film could also be achieved by using conductive atomic force microscopy with platinum-coated probe, which enables fabrication of nano-scale or even molecular-scale device, a significant progress for the ultra-high density data storage application. Mechanism analysis demonstrated that two charge traps with different depth in the molecular backbone were injected by charge carriers progressively as the external bias increased, resulting in the formation of three distinct conductive states (OFF, ON1 and ON2 states). The Royal Society of Chemistry 2012.

Cyclodextrin-induced host-guest effects of classically prepared poly(NIPAM) bearing azo-dye end groups

A thermo-, pH- and cyclodextrin-(CD) responsive poly(N-isopropylacrylamide) (PNIPAM), with a N,N-dimethylaminoazobenzene end group was synthesized. Using 3-mercaptopropionic acid as a chain transfer agent, PNIPAM with a well-defined COOH end group was obtained. The acid end group was transferred to the corresponding acid chloride and then functionalized with N,Ndimethyl[4-(4'- aminophenylazo)phenyl]amine. This dye-end-group-labeled polymer showed acidochromic effects, depending on the pH and the presence of randomly methylated β-cyclodextrin (RAMEB-CD). Also higher cloud-point values for the lower critical solution temperature (LCST) in the presence of RAMEB-CD were observed. Additionally, this azo-dye-end-group-labeled polymer was complexed with hyperbranched polyglycerol (HPG) decorated with β-CD to generate hedgehog-like superstructures.

Azo compounds reducing formation and toxicity of amyloid beta aggregation intermediates

The present invention relates to compounds suitable as modulators of protein misfolding and/or protein aggregation. The compounds are particularly suitable as inhibitors of amyloid aggregate formation and/or modulators of amyloid surface properties, and/or as activators of degradation or reduction of amyloid aggregates.

Visible-light photoresponsivity of a 4-(dimethylamino)azobenzene unit incorporated into single-stranded DNA: Demonstration of a large spectral change accompanying isomerization in DMSO and detection of rapid (Z)-to-(E) isomerization in aqueous solution

We demonstrate significant visible-light photoresponsivity in a synthesized oligonucleotide containing a built-in pseudonucleotide possessing a 4-(dimethylarnino)azobenzene (4-DMAzo) side chain. In dry DMSO as solvent, two clearly distinguishable spectra corresponding to the (E) and (Z) forms of the 4-DMAzo moiety tethered to the oligonucleotide were recorded with a conventional spectrophotometer before and after irradiation with 420 nm wavelength light, which induced (E)-to-(Z) isomerization. In addition, (Z)-to-(E) isomerization was accelerated by irradiation with either visible (λ = 550 nm) or UV (λ = 350 nm) light, demonstrating reversible photoresponsivity of the pseudo-ohgonucleotide. In aqueous solutions the (Z)-to-(E) thermal isomerization of the photoresponsive pseudo-ohgonucleotide was very rapid and was only detectable by laser flash photolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis and characterization of some azo-anil dyes

A number of azo-anil dyes of the type RR'N-φ-N--N-φ-N--6CH-φ-Y with Y=CN or NO2 and R,R′=Me, Me; Me,C6H13; Et,Pr and C6H13,C6,H13 were synthesized by reactions of the aminosubstituted nitrosoamine with phenylene diamine followed by condensation of the resulting aniline with the appropriate 4-substituted benzaldehyde. Mesomorphic properties were determined both by hot-stage polarizing microscopy and DSC. A nematic phase was observed only when R=R′=CH3 while smectic A phases occurred in the other homologs. Melting temperatures were greater than 130°. All had colors ranging from red to orange with UV λmax ranging from 448-459 nm and ε 2.20-3.67 E+4. The ΔH melting values ranged from 16.8 to 30.7 KJ/mole and solubilities in a BDH-E7 liquid crystal mixture were low.

Studies on UV/VIS Absorption Spectra of Azo Dyes. XV. An Analysis of the Absorption Spectra of 4,4'-Diaminoazobenzenes

In the visible absorption spectrum 4,4'-bis-diethylaminoazobenzene shows two absorption maxima (λmax = 426 nm and λmax = 477 nm) with high intensity.Quantum chemical calculations and examinations by peak separation of six 4-substituted azobenzenes and six 4'-substituted 4-diethylaminoazobenzenes (1a-k) indicate that the longest wavelenght band is due to a n-?* transition and the other band is due to a ?-?*-transition.This is verified using an inrement system for ?-?* absorption maxima.A linear relation is found between intensity ratios of the two bands and the HAMMETT-?-constants of the substituents.With increasing electron releasing tendency of the substituents the absorption intensity of the n-?*-band increases.