2491-76-1

Basic information

• Product Name: 4'-CHLORO-4-DIMETHYLAMINOAZOBENZENE
• Synonyms: chlorodimethylaminoazobenzene;n,n-dimethyl-p-((p-chlorophenyl)azo)-anilin;n,n-dimethyl-p-((p-chlorophenyl)azo)aniline;n,n-Dimethyl-p-[(p-chlorophenyl)azo]aniline;N,N-dimethyl-p-[(p-chlorophenyl)azo]-Aniline;p-Chlorodimethylaminoazobenzene;4'-CHLORO-4-DIMETHYLAMINOAZOBENZENE;4-DIMETHYLAMINO-4'-CHLOROAZOBENZENE
• CAS NO: 2491-76-1
• Molecular Formula: C₁₄H₁₄ClN₃
• Molecular Weight: 259.73
• Mol File: 2491-76-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 159 °C
• Boiling Point: 407.06°C (rough estimate)
• Flash Point: 198.2°C
• Appearance: /
• Density: 1.1724 (rough estimate)
• Refractive Index: 1.6010 (estimate)
• PKA: 3.28±0.10(Predicted)
• CAS DataBase Reference: 4'-CHLORO-4-DIMETHYLAMINOAZOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLORO-4-DIMETHYLAMINOAZOBENZENE(2491-76-1)
• EPA Substance Registry System: 4'-CHLORO-4-DIMETHYLAMINOAZOBENZENE(2491-76-1)

Safety Data

• RTECS: BX5060000
• Hazardous Substances Data: 2491-76-1(Hazardous Substances Data)

Usage

General Description

4'-Chloro-4-dimethylaminoazobenzene is a chemical compound commonly used as a dye in the textile industry. It is a yellow to orange crystalline powder and is insoluble in water but soluble in organic solvents. This chemical is known for its strong coloration properties, making it a popular choice for dyeing fabrics and textiles. However, it is also a known carcinogen and has been linked to several health concerns, leading to restrictions on its use in some countries. In addition to its use as a dye, 4'-chloro-4-dimethylaminoazobenzene also has applications in the research and development of new dyes and pigments, as well as in the study of chemical reactions and mechanisms.

Upstream product

• 17333-85-6 4-chlorophenyldiazonium salt 
• 121-69-7 N,N-dimethyl-aniline 
• 82946-80-3 1-(4-N,N'-dimethylaminophenyl)-1-propanol 
• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 106-47-8 4-chloro-aniline 
• 99-98-9 4-amino-N,N-dimethylaniline 

Downstream Products

• 144499-83-2 4-chloro-4'-dimethylamino-3'-heptafluoropropylazobenzene 
• 106-47-8 4-chloro-aniline 
• 99-98-9 4-amino-N,N-dimethylaniline 

Relevant articles and documents

Convenient and rapid diazotization and diazo coupling reaction via aryl diazonium nanomagnetic sulfate under solvent-free conditions at room temperature

For the first time, nanomagnetic-supported sulfonic acid is used for conversion of several types of aromatic amine, containing electron-withdrawing groups as well as electron-donating groups to the corresponding azo dyes in excellent yield. The synthesis of these compounds is described by the sequential diazotization-diazo coupling of various aromatic amines with sodium nitrite, nanomagnetic supported sulfonic acid and coupling agents under solvent-free conditions at room temperature. This new method offers several advantages including short reaction time, mild reaction conditions, avoidance of harmful acids, and simple work-up procedure. More importantly, aryldiazonium salts supported on magnetic nanoparticles (aryl diazonium nanomagnetic sulfate) were sufficiently stable to be kept at room temperature in the dry state.

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.