3010-57-9

Basic information

• Product Name: 4-DIMETHYLAMINO-4'-METHYLAZOBENZENE
• Synonyms: 4’-Methyl-N,N-dimethyl-4-aminoazobenzene;4’-Methyl-p-dimethylaminoazobenzene;Aniline,N,N-dimethyl-p-(p-tolylazo)-;Benzenamine,N,N-dimethyl-4-[(4-methylphenyl)azo]-;Dimethyl-(4-p-tolylazo-phenyl)-amine;n,n-dimethyl-4-((4-methylphenyl)azo)-benzenamin;N,N-Dimethyl-4-(4-methylphenylazo)aniline;n,n-dimethyl-4-(p-tolylazo)-anilin
• CAS NO: 3010-57-9
• Molecular Formula: C₁₅H₁₇N₃
• Molecular Weight: 239.32
• EINECS: 221-135-3
• Mol File: 3010-57-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 165-167 °C
• Boiling Point: 371.98°C (rough estimate)
• Flash Point: 188.1oC
• Appearance: /
• Density: 0.9908 (rough estimate)
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 4-DIMETHYLAMINO-4'-METHYLAZOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-DIMETHYLAMINO-4'-METHYLAZOBENZENE(3010-57-9)
• EPA Substance Registry System: 4-DIMETHYLAMINO-4'-METHYLAZOBENZENE(3010-57-9)

Safety Data

• Hazard Codes: Xn
• Statements: 40-20/21/22
• Safety Statements: 45-36/37
• RTECS: BX8400000
• Hazardous Substances Data: 3010-57-9(Hazardous Substances Data)

Usage

General Description

4-DIMETHYLAMINO-4'-METHYLAZOBENZENE is an aromatic azo compound with the chemical formula C14H16N2. It is used as a dye in the textile and food industries, as well as a pH indicator in chemical analysis. The compound is a bright red-orange crystalline powder that is insoluble in water but soluble in organic solvents. Its azo group gives it the characteristic color, and it is known to be a mutagenic and potentially carcinogenic compound, so precautions must be taken when handling it. It is also used in the synthesis of other organic compounds and in research labs as a biological stain.

Upstream product

• 106-49-0 p-toluidine 
• 121-69-7 N,N-dimethyl-aniline 
• 785-86-4 1,3-di(p-tolyl)triaz-1-ene 

Downstream Products

• 106-49-0 p-toluidine 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 144499-84-3 4-dimethylamino-3-heptafluoropropyl-4'-methylazobenzene 

Relevant articles and documents

Liquid azo dyes

Any liquid azo dyes, in which auxochrome such as dialkylamino, alkoxy, and amino group is attached in a molecule, were produced. In a series of 2-alkyl-4'-(dimethylamino)azobenzenes, the butyl, hexyl, octyl, and dodecyl derivatives were liquid at room temperature, whereas the propyl, 1-methylethyl, 1-methylpropyl, 1,1-dimethylethyl, and octadecyl derivatives were solid. Thus, it is essential for liquid azo dyes to have a medium n-alkyl group at the 2-position. In a series of 2-butyl-4'-(dialkylamino)azobenzenes, the dimethylamino, diethylamino, dibutylamino, dioctylamino, and didodecylamino derivatives were liquid. 2-Butyl-4'-methoxyazobenzene and 4-amino-3,5-dimethyl-2'-butylazobenenzne were also liquid, whereas 2-butyl-4'-hydroxyazobenznene, 4-amino-2'-butylazobenzene, and 2-butyl-4'-(methylamino)azobenzene were solid. The prevention of π/π stacking, alkyl-alkyl interactions, and intermolecular hydrogen bond could produce liquid azo dyes.

Possibility of the Intarmolecularity of Triazene Rearrangement

The mechanism for the ortho-rearrangement of diaryltriazenes still remains equivocal.An interesting result suggesting an intramolecular nature of the triazene rearrangement was obtained on the basis of the effect of concentration of added N,N-dimethylaniline in the ortho-rearrangement of 1,3-bis(4-methylphenyl)triazene (1).The ortho/para ratio for the rearrangement of 1,3-diphenyltriazene (4) tends to increase with an increase of the viscosity.The results are discussed on the basis of increasing nucleophilicity of free amine by H-bonding with dimethylaniline and favoring ortho-migratrion with viscosity, respectively.