60-11-7

Usage

Uses

Used in the Chemical Industry:
Solvent Yellow 2 is used as a pH indicator, with a color change from red at pH 2.9 to yellow at pH 4.0. This property makes it useful for determining the acidity or alkalinity of solutions in various chemical applications.
Used in the Pharmaceutical Industry:
In the past, Solvent Yellow 2 was used as a coloring agent in the pharmaceutical industry. Its vibrant yellow color added visual appeal to medications, although it is now considered a banned food coloring due to potential health risks.
Used in the Food Industry:
Although now banned, Solvent Yellow 2 was formerly used as a coloring agent in the food industry. Its bright yellow hue was utilized to enhance the appearance of various food products.
Used in the Cosmetics Industry:
Similar to its use in the pharmaceutical and food industries, Solvent Yellow 2 was also employed as a coloring agent in cosmetics. Its ability to provide a vivid yellow color made it a popular choice for cosmetic products.
Used in the Laboratory:
Solvent Yellow 2 serves as a laboratory reagent and is used for the determination of free hydrochloric acid in gastric juice and the spot test identification of peroxidized fats. Its chemical properties make it a valuable tool in scientific research and analysis.
Used in the Aviation Industry:
Solvent Yellow 2 is utilized as a stability agent for aviation fuel, specifically for TETRAETHYLLEAD. Its role in ensuring the stability of aviation fuel contributes to the safe and efficient operation of aircraft.

Preparation

aniline diazotization, and N,N-dimethylaniline coupling.

Production Methods

4-Dimethylaminoazobenzene was produced in large quantities in the early 1900s but is currently not produced in any significant commercial quantity in the United States.

Air & Water Reactions

Dust may form an explosive mixture in air. Insoluble in water.

Reactivity Profile

Solvent Yellow 2 can detonate, particularly if sensitized by the presence of metal salts or strong acids. May form toxic gases with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. May form flammable gases with alkali metals. May react explosively with strong oxidizing agents, metal salts, peroxides, and sulfides. May react explosively with strong oxidizing agents, metal salts, peroxides, and sulfides.

Health Hazard

4-Dimethylamino-azobenzene (XIII) is the parent compound of the amino-azo dye carcinogens; it is also known in the earlier literature as Butter Yellow, because it was used to color butter and vegetable oils before its carcinogenic activity was discovered. Many derivatives of XIII have been prepared and tested for carcinogenic activity. In the rat, the amino-azo dye carcinogens, administered in the diet, specifically induce hepatomas. Tumor induction by most of the amino-azo dyes is delayed or inhibited by high dietary levels of riboflavin (vitamin B2) or protein. Replacement of the –N=N– azo linkage by –CH=CH–, as in 4-dimethylaminostilbene (XIV), results in widening the target tissue spectrum; XIV induces tumors in the liver, mammary gland, and ear duct. Mice are much more resistant than rats to the carcinogenic activity of both amino-azo dyes and aminostilbenes.

Fire Hazard

Flash point data for Solvent Yellow 2 are not available. Solvent Yellow 2 is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx

Carcinogenicity

4-Dimethylaminoazobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.

Environmental fate

Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and Lewis, 1987). At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 249, 140, 83, and 48 mg/g, respectively (Dobbs and Cohen, 1980).

Standard

Light Fastness

Melting point

Stable

ISO

General

Purification Methods

Crystallise the dye from acetic acid or isooctane, or from 95% EtOH by adding hot water and cooling. Dry it over KOH under vacuum at 50o. [Beilstein 6 IV 448.] CARCINOGEN.

Toxicity evaluation

Butter yellow exists as a stable crystalline material at normal temperature and pressure. It is insoluble in water, but soluble in organic solvents such as alcohol, chloroform, ether, petroleum ether, mineral acids, oils, and pyridine. Its octanol/water partition coefficient is 4.58, vapor pressure is 3.3×10-7 mm Hg; and Henry’s law constant is 7.1×10-9 atm-m3 mol-1. Butter yellow may be released into the environment as a result of its manufacture and use in the consumer products. It may bind to the soil and when released into water, may bioconcentrate in aquatic organisms, or may be adsorbed into the sediment. If released in the atmosphere, it may undergo direct photolysis.

InChI:InChI=1/C14H15N3/c1-17(2)14-10-8-13(9-11-14)16-15-12-6-4-3-5-7-12/h3-11H,1-2H3

Upstream product

• 2684-02-8 benzenediazonium 
• 121-69-7 N,N-dimethyl-aniline 
• 34885-34-2 phenyldiazonium acetate 
• 62-53-3 aniline 
• 138-89-6 p-dimethylaminonitrosobenzene 
• 621-90-9 N-methyl-4-aminoazobenzene 
• 74-88-4 methyl iodide 
• 82946-80-3 1-(4-N,N'-dimethylaminophenyl)-1-propanol 
• 2747-31-1 4-(phenylazo)-N,N-dimethylaniline amino oxide 
• 13921-67-0 4-(phenyl-ONN-azoxy)-N,N-dimethylaniline amino oxide 
• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 109057-65-0 C₁₆H₁₂N₂O 
• 614-01-7 N-phenyl-N-nitrosohydrazine 

Downstream Products

• 85074-39-1 N,N-dibutyl-N',N'-dimethyl-p-phenylenediamine 
• 2350-78-9 trans-N,N,N-trimethyl-4-(phenylazo)benzenammonium iodide 
• 2747-31-1 4-(phenylazo)-N,N-dimethylaniline amino oxide 
• 2491-74-9 N,N-dimethyl-4-(4-nitrophenylazo)aniline 
• 69127-76-0 4-heptafluoropropyl-N,N-dimethylaniline 
• 144499-72-9 4-dimethylamino-4'-heptafluoropropylazobenzene 
• 2350-78-9 4-(phenylazo)-N,N-dimethylaniline methiodide 
• 14135-50-3 4-(phenyl-NNO-azoxy)-N,N-dimethylaniline amino oxide 
• 13921-67-0 4-(phenyl-ONN-azoxy)-N,N-dimethylaniline amino oxide 
• 100-34-5 benzene diazonium chloride 
• 51105-04-5 Dimethyl-(2-nitro-4-phenylazo-phenyl)-amine 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 621-90-9 N-methyl-4-aminoazobenzene 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Strong Inhibition of Cis-Trans Isomerization of Azo Compounds by Hydroxide Ion

The thermal cis-trans isomerization rate of methyl yellow (1), p-phenyl red (2), and o-methyl red (3) in aqueous solution was measured at different hydroxide ion concentrations, and it was found that there is a very strong inhibition as the pH increases.For 1 the rate changes from 2.17*10-2 s-1 at NaOH 6*10-3 M to 1.0*10-3 s-1 at NaOH 0.1 M.The observed rate constant for 2 was too fast for the experimental technique used at a concentration of NaOH lower than 0.01 M.These results are interpreted in terms of a much faster rate of isomerization of the protonated cis compounds than the neutral ones, and values for the pKa and rate constants for both species are calculated.

Photochromic behavior in the molecular glass of 4,4′,4″-tris(3-methylphenyphenylamino)triphenylamine

For the purpose of gaining information on the microstructure of molecular glasses, photochromic behavior of 4-dimethyl-aminoazobenzene (DAAB) in the molecular glass of 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA) was studied in comparison with that in a polystyrene matrix and in a benzene solution. The results strongly suggest that the local free volume in the molecular glass of m-MTDATA is smaller than that in the polystyrene glass.

Photochromic reaction in a molecular glass as a novel host matrix: The 4-dimethylaminoazobenzene-4,4′,4″-tris [3-methylphenyl(phenyl)amino]triphenylamine system

For the purposes of clarifying the properties of a molecular glass as a novel host matrix and gaining information on the microstructure of the molecular glass, the photochromic behavior of 4-dimethylaminoazobenzene (DAAB) in a novel molecular glass of 4,4′,4″-tris[3-methylphenyl(phenyl)amino]triphenylamine (m-MTDATA) was investigated, and compared with its behavior in a polystyrene glass matrix and a benzene solution. It was found that the fraction of the photoisomerized cis-isomer of DAAB at the photostationary state is smaller in the m-MTDATA glass matrix than in the polystyrene matrix and the benzene solution, and that the apparent initial rate constant for the backward cis→trans thermal isomerization of DAAB is much larger in the m-MTDATA glass than in the polystyrene matrix and the benzene solution. These results suggest that the average size of local free volume in the molecular glass of m-MTDATA is smaller than that in the polystyrene glass.

Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions

Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer-Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component.

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Method for preparing asymmetric azobenzene and azobenzene oxide compounds through photocatalysis

The invention relates to a method for preparing asymmetric azobenzene and azobenzene oxide compounds through photocatalysis. Through a photocatalyst, an aromatic nitro compound reacts with an aromaticamino compound under the conditions of illumination and inert gas to obtain an asymmetric azobenzene compound represented by a formula I and an asymmetric azoxybenzene compound represented by a formula II; the method can be used for replacing a conventional mature organic synthesis process, has the advantages of mild conditions, high selectivity and universality, and is suitable for industrial production.

Trichloroisocyanuric Acid Mediated Oxidative Dehydrogenation of Hydrazines: A Practical Chemical Oxidation to Access Azo Compounds

A highly efficient, metal-free, chemical oxidation of hydrazines has been implemented using environmentally friendly TCCA as oxidant. This benign protocol provides straightforward access to a wide range of azo compounds in THF in excellent yield. Altogether, 35 azo compounds were obtained in this way and scale-up preparations were performed. Additionally, a plausible mechanism was also proposed. Step-economical process, mild reaction conditions, operational simplicity, high reaction efficiency, and easy scale-up highlight the practicality of this methodology.

Hole Catalysis as a General Mechanism for Efficient and Wavelength-Independent Z → E Azobenzene Isomerization

Whereas the reversible reduction of azobenzenes has been known for decades, their oxidation is destructive and as a result has been notoriously overlooked. Here, we show that a chain reaction leading to quantitative Z → E isomerization can be initiated before reaching the destructive anodic peak potential. This hole-catalyzed pathway is accessible to all azobenzenes, without exception, and offers tremendous advantages over the recently reported reductive, radical-anionic pathway because it allows for convenient chemical initiation without the need for electrochemical setups and in the presence of air. In addition, catalytic amounts of metal-free sensitizers, such as methylene blue, can be used as excited-state electron acceptors, enabling a shift of the excitation wavelength to the far red of the azobenzene absorption (up to 660 nm) and providing quantum yields exceeding unity (up to 200%). Our approach will boost the efficiency and sensitivity of optically dense liquid-crystalline and solid photoswitchable materials. Video Abstract: [Figure presented] Molecular switches are a key ingredient in stimulus-responsive and adaptive materials and devices. Light is among the most attractive stimuli, yet photoswitches often require intense irradiation with high-energy UV light and suffer from inefficient switching as well as fatigue. Thus, the design of robust and efficient photoswitches constitutes an important challenge to boost the sensitivity and energy efficiency of the respective materials and devices. Here, we describe that the isomerization of azobenzene switches from their less stable Z isomer back to the more stable E isomer can be triggered by tiny, i.e., catalytic, amounts of holes caused by chemical, electrochemical, or photochemical oxidation. Our method is generally applicable to the entire family of azobenzene switches, does not require expensive equipment, and allows the reliable and efficient operation of these photoswitches by using red light with quantum efficiencies up to 200%. An efficient and generally applicable method is developed for operating azobenzene molecular switches by using catalytic amounts of holes (via an oxidant) or photons (via a photosensitizer). The pathway allows for indirect Z → E photoisomerization using lower-energy light than required for direct azobenzene excitation and with high quantum yields exceeding unity. The method should help to enhance the sensitivity of photoresponsive materials and devices with high optical density.

Method for highly stereoselective preparation of trans-aromatic tertiary amine azo compound

The invention provides a method for efficient and highly stereoselective preparation of an azo compound through para C-H bond selective activity of an organic aromatic tertiary amine. According to themethod, a Bronsted acid is adopted as a catalyst, an aromatic diazonium tetrafluoroboric acid compound and an organic aromatic tertiary amine compound are adopted as reaction substrates, and an organic solvent is put into a reaction system. The method has the advantages that the catalyst is cheap and easy to obtain, high in substrate applicability, gentle in reaction condition and safe and reliable; the selectivity of a target product is approximate to 100%, the E/Z selectivity of the target product is greater than 99:1, and relatively high yield is achieved; and by adopting the method, the defects that a conventional method for synthesizing different aromatic functional groups to replace organic aromatic tertiary amine azo compounds is harsh in reaction condition, poor in reaction selectivity, tedious in experiment step, low in yield, harmful to the environment since reagents harmful to the environment are used, and the like, can be overcome, and good industrial application prospectscan be achieved. The invention further provides an organic aromatic tertiary amine azo compound with different aryl substituted functional groups.

Azo disperse dyes and sublimation transferring ink comprising thereof

The present invention relates to a sublimation transfer ink which is used in digital textile printing (DTP). The present invention provides an azo-based disperse dye represented by chemical formula 1 and a sublimation transfer ink comprising the azo-based disperse dye. In chemical formula 1, R_1 and R_2 are each independently an alkyl group having 6 to 8 carbon atoms, R_3 is each independently H, NO_2 or SCO_2H_3, R_4 and R_5 are each independently H, NO_2, Cl or CN, R_6 is each independently H or NHCO_2CH_3, and R_7 is each independently H, CH_3, OCH_3, or OCH_2CH_3. The azo-based disperse dye and the transfer ink comprising the azo-based disperse dye can be used as a transfer ink specified to DTP since the azo-based disperse dye and the transfer ink comprising the azo-based disperse dye are not only excellent in transfer efficiency for fabrics such as a polyester fabric and the like, but also very excellent in washing fastness and light fastness.COPYRIGHT KIPO 2018