17576-88-4

Basic information

• Product Name: 4-[(E)-(3-bromophenyl)diazenyl]-N,N-dimethylaniline
• CAS NO: 17576-88-4
• Molecular Formula: C₁₄H₁₄BrN₃
• Molecular Weight: 304.1851
• Mol File: 17576-88-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 421.6°C at 760 mmHg
• Flash Point: 208.8°C
• Density: 1.31g/cm³
• Vapor Pressure: 2.58E-07mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: 4-[(E)-(3-bromophenyl)diazenyl]-N,N-dimethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(E)-(3-bromophenyl)diazenyl]-N,N-dimethylaniline(17576-88-4)
• EPA Substance Registry System: 4-[(E)-(3-bromophenyl)diazenyl]-N,N-dimethylaniline(17576-88-4)

Safety Data

• Hazardous Substances Data: 17576-88-4(Hazardous Substances Data)

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 591-19-5 m-Bromoaniline 

Downstream Products

• 20893-74-7 3-bromophenyldiazonium chloride 

Relevant articles and documents

Activation of the aryl hydrocarbon receptor by methyl yellow and related congeners: structure-activity relationships in halogenated derivatives.

The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates the biological action of many environmental compounds. Methyl yellow (4-dimethylaminoazobenzene; MY) is a principal azo-dye, and structurally related compounds were subjected to analysis of structure-activity relationships as AhR ligands by using a yeast AhR signaling assay. The effects of halogen-substitution among 23 halogenated MYs on the AhR ligand activity can be summarized as follows: enhancement by halogen-substitution at the ortho-position (2'- and 6'-position), and reduction by substitution at the para-position (4'-position). The greatest enhancement of the ligand activity was observed in 2',6'-dichlorinated MY (13.5-fold of MY), and its AhR ligand activity was very close to that of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the present assay system. In the study of compounds structurally related to MY, benzanilide (BA) showed almost the same AhR ligand activity as azobenzene and trans-stilbene. Furthermore, 4'-chlorobenzanilide, in which the length of the molecule is similar to that of MY, enhanced the AhR ligand activity by ortho(2')-chlorine-substitution, and the AhR ligand activity of 2',4'-dichlorobenzanilide was similar to that of 2'-chloro-MY. These results suggest that the amide bond is equivalent to the -N=N- or -CH=CH- double bond for recognition as the ligand by AhR in 1,2-diphenyl-1,2-ene derivatives.