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

Description

N,N-DIMETHYL-4,4'-AZODIANILINE is a disperse dye characterized by its dark orange to rust brown crystalline powder appearance. It exhibits various color properties in different chemical environments, such as light yellow in strong sulfuric acid, orange-red in diluted sulfuric acid, red in nitric acid, and red in strong hydrochloric acid. It remains unchanged in the presence of sodium hydroxide solution.

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

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

Downstream Products

• 1591-56-6 acetic acid-[4-(4-dimethylamino-phenylazo)-anilide] 
• 79307-81-6 chloro-acetic acid-[4-(4-dimethylamino-phenylazo)-anilide] 
• 83922-67-2 4-octanoylamino-4'-(dimethylamino)azobenzene 
• 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 
• 765303-90-0 4-{6-[(E)-(4-{(E)-[4-(dimethylamino)phenyl]diazenyl)phenyl)-diazenyl]-2,3-dihydro-1H-perimidin-2-yl}-phenol 
• 1338925-82-8 C₂₇H₂₄N₄ 
• 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 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.