60-11-7 Usage
Description
4-N,N-Dimethylaminobenzene diazonium chloride is a
diazo compound found in diazo copy paper. It is
allergenic only when unexposed.
Chemical Properties
yellow to orange crystalline powder
Uses
Different sources of media describe the Uses of 60-11-7 differently. You can refer to the following data:
1. For determination of free HCl in gastric juice; spot test identification of peroxidized fats; pH indicator (red 2.9, yellow 4.0).
2. Formerly used as a coloring agent in
foods, drugs, and cosmetics
3. Butter yellow was largely used as a food coloring agent. It was
also used for the determination of free hydrochloric acid in
gastric juice, for the spot test identification of peroxidized fats,
as a pH indicator, and as a laboratory reagent.
Preparation
aniline diazotization, and N,N-dimethylaniline coupling.
Definition
A banned food coloring.
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.
General Description
Yellow crystalline leaflets or an orange powder.
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).
Properties and Applications
yellow to red light yellow. Light yellow powder, melting point 115 ℃ (yellow flaky crystal). Insoluble in water, soluble in ethanol for yellow solution, in oil soluble. In concentrated sulfuric acid to yellow, red after diluted solution; . Mainly used for Aviation fuel TETRAETHYLLEAD stability agent and pH indicator, also used in paraffin, polystyrene, oil and soap stain
Standard
Light Fastness
Heat-resistant(℃)
Water
Sodium Carbonate(5%)
Hydrochloric acid(5%)
Melting point
Stable
ISO
General
113.5-115
120
Poor
Well
Poor
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.
Check Digit Verification of cas no
The CAS Registry Mumber 60-11-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 60-11:
(4*6)+(3*0)+(2*1)+(1*1)=27
27 % 10 = 7
So 60-11-7 is a valid CAS Registry Number.
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
60-11-7Relevant articles and documents
Strong Inhibition of Cis-Trans Isomerization of Azo Compounds by Hydroxide Ion
Sanchez, Ana,Rossi, Rita H. de
, p. 2094 - 2096 (1993)
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.
-
Hromatka,Schlager
, p. 29,31 (1954)
-
Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions
Gingrich, Phillip W.,Olson, David E.,Tantillo, Dean J.,Tombari, Robert J.,Tuck, Jeremy R.,Yardeny, Noah
supporting information, p. 7575 - 7580 (2021/09/22)
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.
Method for preparing asymmetric azobenzene and azobenzene oxide compounds through photocatalysis
-
Paragraph 0028-0030; 0059; 0060, (2020/02/27)
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.
Hole Catalysis as a General Mechanism for Efficient and Wavelength-Independent Z → E Azobenzene Isomerization
Goulet-Hanssens, Alexis,Rietze, Clemens,Titov, Evgenii,Abdullahu, Leonora,Grubert, Lutz,Saalfrank, Peter,Hecht, Stefan
supporting information, p. 1740 - 1755 (2018/06/29)
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.