5042-54-6

Basic information

• Product Name: 5-(phenylazo)toluene-2,4-diamine
• Synonyms: 5-(phenylazo)toluene-2,4-diamine;ChrysoidineRVbase;2,4-DIAMINO-5-METHYLAZOBENZENE;4-Methyl-6-(phenylazo)-1,3-benzenediamine;C.I.11320:1;C.I.Solvent Orange 4;Chrysoidine R Base;(5-amino-2-methyl-4-phenylazo-phenyl)amine
• CAS NO: 5042-54-6
• Molecular Formula: C13H14N4
• Molecular Weight: 226.27706
• EINECS: 225-736-1
• Mol File: 5042-54-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 357.89°C (rough estimate)
• Flash Point: 225.1°C
• Appearance: /
• Density: 1.0439 (rough estimate)
• Vapor Pressure: 3.08E-08mmHg at 25°C
• Refractive Index: 1.4850 (estimate)
• CAS DataBase Reference: 5-(phenylazo)toluene-2,4-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(phenylazo)toluene-2,4-diamine(5042-54-6)
• EPA Substance Registry System: 5-(phenylazo)toluene-2,4-diamine(5042-54-6)

Safety Data

• Hazardous Substances Data: 5042-54-6(Hazardous Substances Data)

Usage

Description

5-(phenylazo)toluene-2,4-diamine is an organic compound characterized by its orange color and a melting point of 165-166°C. It is soluble in water, ethanol, acetone, and Cellosolve. 5-(phenylazo)toluene-2,4-diamine exhibits color changes in the presence of different acids, turning yellow in concentrated sulfuric acid and orange upon dilution, and red in concentrated hydrochloric acid. Its aqueous dye solution turns red upon the addition of hydrochloric acid and yields a yellow precipitate when mixed with sodium hydroxide.

Uses

Used in Dye Industry:
5-(phenylazo)toluene-2,4-diamine is used as a dye for its color-changing properties in response to different acids, making it suitable for applications that require pH-sensitive color indicators or specific coloration effects.
Used in Analytical Chemistry:
5-(phenylazo)toluene-2,4-diamine is used as a reagent in analytical chemistry for the detection and determination of metal ions, particularly due to its ability to form colored complexes with certain metals.
Used in Textile Industry:
5-(phenylazo)toluene-2,4-diamine is used as a dye in the textile industry for coloring fabrics, taking advantage of its solubility in water and its color-changing properties to create unique and vibrant patterns.
Used in Plastics and Polymer Industry:
5-(phenylazo)toluene-2,4-diamine is used as a colorant in the plastics and polymer industry to impart specific colors to various plastic products, utilizing its solubility and color-changing characteristics.
Used in Paper Industry:
5-(phenylazo)toluene-2,4-diamine is used as a dye in the paper industry for coloring paper products, providing a range of color options and enabling the creation of visually appealing paper materials.

Preparation

aniline diazotization, and 4-Methylbenzene-1,3-diamine coupling, and made free base.

Standard

Light Fastness

Melting point

Stable

ISO

Poor

InChI:InChI=1/C13H14N4/c1-9-7-13(12(15)8-11(9)14)17-16-10-5-3-2-4-6-10/h2-8H,14-15H2,1H3

Upstream product

• 27329-27-7 4-methyl-2-nitrobenzoic acid 
• 95-80-7 4-methylbenzene-1,3-diamine 
• 619-97-6 benzenediazonium nitrate 
• 100-34-5 benzene diazonium chloride 
• 2684-02-8 benzenediazonium 

Downstream Products

• 63517-77-1 5-methyl-2,7-diphenyl-2,7-dihydro-benzo[1,2-d;3,4-d']bistriazole 
• 120401-84-5 2,5-Dimethyl-8,11-diphenyl-8,11-dihydro-3,4,7,8,9,10,11,12-octaaza-dicyclopenta[c,g]phenathrene 
• 120401-85-6 5,11-Dimethyl-2,8-diphenyl-2,8-dihydro-1,2,3,6,7,8,9,12-octaaza-dicyclopenta[a,h]anthracene 
• 82811-23-2 5-amino-6-methyl-2-phenylbenzotriazole 
• 20828-45-9 N,N'-(4-methyl-6-phenylazo-m-phenylene)-bis-acetamide 
• 63517-76-0 4-methyl-2,6-bis-phenylazo-m-phenylenediamine 
• 861558-54-5 N³-(2,4-dinitro-phenyl)-4-methyl-6-phenylazo-m-phenylenediamine 

Relevant articles and documents

Tricyclic compound as plasma kallikrein inhibitor and application thereof

The invention provides a tricyclic plasma kallikrein inhibitor compound which is novel in structure, good in activity and high in selectivity. The tricyclic plasma kallikrein inhibitor compound can be widely applied to prevention or treatment of diseases related to plasma kallikrein activity.

Synthesis and Quantitative Structure-Activity Relationships of Selective BCRP Inhibitors

The breast cancer resistance protein (BCRP/ABCG2) is a member of the ABC transporter superfamily. This protein has a number of physiological functions, including protection of the human body from xenobiotics. The overexpression of BCRP in certain tumor cell lines causes cross-resistance against various drugs used in chemotherapeutic treatment. In a previous work we showed that a new class of compounds derived from XR9576 (tariquidar) selectively inhibits BCRP. In this work we synthesized more members of this class, with modification on the second and third aromatic rings. The inhibitory activities against BCRP and P-gp were assayed using a Hoechst 33342 assay for BCRP and a calcein AM assay for P-gp. Finally, quantitative structure-activity relationships for both aromatic rings were established. The results obtained show the importance of the electron density on the third aromatic ring, influenced by substituents, pointing to interactions with aromatic residues of the protein binding site. In the second aromatic ring the activity of compounds is influenced by the steric volume of the substituents.

Structure-activity relationships of substituted benzothiophene-anthranilamide factor Xa inhibitors

Compound 1 was identified by high throughput screening as a novel, potent, non-amidine factor Xa inhibitor with good selectivity against thrombin and trypsin. A series of modifications of the three aromatic groups of 1 was investigated. Substitution of chlorine or bromine for fluorine on the aniline ring led to the discovery of subnanomolar factor Xa inhibitors. Positions on the anthranilic acid ring that can accommodate further substitution were also identified.