539-17-3

Basic information

• Product Name: N,N-DIMETHYL-4,4'-AZODIANILINE
• Synonyms: N,N-DIMETHYL-4,4'-AZODIANILINE;N,N-DIMETHYL-4,4-AZODIANILINE;P,P'-DIMAPA-ANILINE;CI 11025;(E)-4-((4-AMINOPHENYL)DIAZENYL)-N,N-DIMETHYLANILINE;DISPERSE BLACK 3;4-(4-DIMETHYLAMINOPHENYLAZO)ANILINE;4-AMINO-4'-DIMETHYLAMINOAZOBENZENE
• CAS NO: 539-17-3
• Molecular Formula: C14H16N4
• Molecular Weight: 240.3
• EINECS: 208-712-5
• Mol File: 539-17-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 190-195 °C (dec.)
• Boiling Point: 373.02°C (rough estimate)
• Flash Point: 214.5°C
• Appearance: /
• Density: 1.0236 (rough estimate)
• Vapor Pressure: 1.23E-07mmHg at 25°C
• Refractive Index: 1.4850 (estimate)
• Storage Temp.: 2-8°C
• PKA: 3.43±0.10(Predicted)
• Water Solubility: 120.2ug/L(25 oC)
• BRN: 748253
• CAS DataBase Reference: N,N-DIMETHYL-4,4'-AZODIANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYL-4,4'-AZODIANILINE(539-17-3)
• EPA Substance Registry System: N,N-DIMETHYL-4,4'-AZODIANILINE(539-17-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: BX5020000
• F: 8-9-23
• Hazardous Substances Data: 539-17-3(Hazardous Substances Data)

Usage

Chemical Properties

dark orange to rust brown crystalline powder

Uses

N,?N-?Dimethyl-?4,?4''-?azodianiline is a disperse dye. Dyes and metabolites.

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

Properties and Applications

black, red and black. Red crystallization, melting point of 186 ~ 187 ℃. Soluble in ethanol, acetone, soluble fiber element, pottery, solvent and carbon tetrachloride,. The strong sulfuric acid is palm in light yellow, diluted for orange red; In the light of nitric acid for palm red solution; In strong hydrochloric acid solution for red; In the thick of sodium hydroxide solution don’t change color. Standard(Polyamide) Ironing Fastness Light Fastness Persperation Fastness Washing Fastness Fading Stain Fading Stain Fading Stain ISO 2 3 4 3-4 4 4

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 
• 119428-81-8 1,4-diamino-2-(4-dimethylaminophenylazophenylamino)anthraquinone 
• 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 

Relevant articles and documents

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.

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.

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.