Solvent Yellow 2
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Solvent Yellow 2
structure -
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CAS No:
60-11-7
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Formula:
C14H15N3
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Chemical Name:
Solvent Yellow 2
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Synonyms:
4-(Dimethylamino)azobenzol;4-(Dimethylamino)phenylazobenzene;4-(Phenylazo)-N,N-dimethylaniline;4-Dimethylaminoazobenzene,CI 11020;4-Dimethylaminoazobenzene,CI 11020 ph.eur;brilliantfastyellow;Butter OR Methyl Yellow;ButteryellowMethylyellow
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CAS No:
Description
yellow to orange crystalline powder
4-dimethylaminoazobenzene appears as yellow crystalline leaflets or an orange powder. (NTP, 1992)|YELLOW CRYSTALS.|Yellow, leaf-shaped crystals.
4-dimethylaminoazobenzene appears as yellow crystalline leaflets or an orange powder. (NTP, 1992)|4-(dimethylamino)azobenzene is a member of azobenzenes.|4-Dimethylaminoazobenzene is used as a dye for coloring polishes, wax products, and soap. Acute (short- term) dermal exposure to 4-dimethylaminoazobenzene may result in contact dermatitis in humans. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of 4-dimethylaminoazobenzene in humans. Animal studies have reported birth defects in the offspring of mice exposed to 4-dimethylaminoazobenzene and tumors of the lung, liver, and bladder from oral exposure to 4-dimethylaminoazobenzene. EPA has not classified 4-dimethylaminoazobenzene for carcinogenicity. The International Agency for Research on Cancer (IARC) has classified 4- dimethylaminoazobenzene as a Group 2B, possibly carcinogenic to humans.|4-Dimethylaminoazobenzene is a yellow, crystalline solid compound. 4-Dimethylaminoazobenzene was used as a dye for coloring polishes, wax products, polystyrene and soap, and was also used as a pH indicator, but is no longer used or produced in the United States. Exposure to this substance causes dermatitis. 4-dimethylaminoazobenzene is reasonably anticipated to be a human carcinogen. (NCI05)|A reagent used mainly to induce experimental liver cancer. According to the Fourth Annual Report on Carcinogens (NTP 85-002, p. 89) published in 1985, this compound "may reasonably be anticipated to be a carcinogen." (Merck, 11th ed)
4-N,N-Dimethylaminobenzene diazonium chloride is a diazo compound found in diazo copy paper. It is allergenic only when unexposed.
A banned food coloring.
Solvent Yellow 2 Basic Attributes
225.29
225.29
746016
200-455-7
A49L8E13FD
1498
6236
2811|3143|3077
TSCA listed
DTXSID5020491
C44324
Yellow
29270000
Characteristics
408nm, 256nm, 508nm
28
4.58
Yellow Powder
1.1303 (rough estimate)
111 °C (dec.)(lit.)
356.8°C (rough estimate)
178.2±23.2 °C
1.5770 (estimate)
13.6 mg/L
Store at RT.
3 x 10-7mmHg (estimated, NIOSH, 1997)
7.78
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-m3mol-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.
2.9-4.0
3.226(at 25℃)
1.4×103mol/(m3Pa) at 25℃, HSDB (2015)
Dust may form an explosive mixture in air. Insoluble in water.
Amines, Phosphines, and Pyridines
Explosive
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.
Store at RT.
Safety Information
III
6.1
UN 2811 6.1/PG 3
3
T
36/37-45-53-22
BX7350000
T
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with DAB youshould be trained on its proper handling and storage. Storein a cool, dry place and protect from exposure to light andair. A regulated, marked area should be established wherethis chemical is handled, used, or stored in compliance withOSHA Standard 1910.1045.
Stable, but heat and light sensitive. Incompatible with strong oxidizing agents, strong acids.
P281-P301 + P310
Carcinogen.
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U093, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... Summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for 4-(DIMETHYLAMINO)AZOBENZENE (7 total), please visit the HSDB record page.
None reported.
Toxicology Review: L'alimentation et la Vie 50: 77 (1962)|Toxicology Review: British Journal of Cancer 6: 270 (1952)|Toxicology Review: Advances in Chemistry Series 13: 271 (1970)|Toxicology Review: Journal of Nutrition 44: 345 (1951)|For more Special Reports (Complete) data for 4-(DIMETHYLAMINO)AZOBENZENE (6 total), please visit the HSDB record page.
UN 2811 6.1/PG 3
Flash point data for Solvent Yellow 2 are not available. Solvent Yellow 2 is probably combustible.
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P310, P308+P313, P321, P330, P405, and P501|Aggregated GHS information provided by 51 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P264, P280, P281, P302+P352, P308+P313, P321, P332+P313, P362, P405, and P501|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|In case of fire in the surroundings, use appropriate extinguishing media.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Workers exposed to DAB should wear personal protective equipment & their work should be carried out only in restricted areas.|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|For more Personal Protective Equipment (PPE) (Complete) data for 4-(DIMETHYLAMINO)AZOBENZENE (8 total), please visit the HSDB record page.|(See protection codes)
PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... . Filter housing that is designed so that used filters can be transferred into plastic bags without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... . The plastic bag should be sealed immediately ... . The sealed bag should be labelled properly ... . Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bags, so that outer surface ... is not contaminated ... . The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
Clothing & equipment after use should be placed in an impervious container for decontamination or disposal.|PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for 4-(DIMETHYLAMINO)AZOBENZENE (14 total), please visit the HSDB record page.
Workers' exposure to 4-dimethylaminoazobenzene is to be controlled through the required use of engineering controls, work practices, & personal protective equipment, incl respirators. Identified as an occupational carcinogen without establishing a PEL.
NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.|NIOSH considers 4-dimethylaminoazobenzene to be a potential occupational carcinogen.
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.
Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
The substance is irritating to the eyes, skin and respiratory tract.
Repeated or prolonged contact with skin may cause dermatitis. This substance is possibly carcinogenic to humans.
PREVENT DISPERSION OF DUST! AVOID ALL CONTACT!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety goggles or eye protection in combination with breathing protection.
Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 4-(Dimethylamino)azobenzene is included on this list.
4-Dimethylaminoazobenzene is used as a dye for coloring polishes, wax products, and soap. Acute (short- term) dermal exposure to 4-dimethylaminoazobenzene may result in contact dermatitis in humans. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of 4-dimethylaminoazobenzene in humans. Animal studies have reported birth defects in the offspring of mice exposed to 4-dimethylaminoazobenzene and tumors of the lung, liver, and bladder from oral exposure to 4-dimethylaminoazobenzene. EPA has not classified 4-dimethylaminoazobenzene for carcinogenicity. The International Agency for Research on Cancer (IARC) has classified 4- dimethylaminoazobenzene as a Group 2B, possibly carcinogenic to humans.
U093; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
U093; As stipulated in 40 CFR 261.33, when p-dimethylaminoazobenzene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Toxicity
DIETS HIGH IN RIBOFLAVIN OR SUPPLEMENTED WITH POLYCYCLIC HYDROCARBONS, WHICH REDUCED TUMOR INDUCTION BY AZO DYES, ALSO LOWERED BINDING OF DYES TO PROTEIN FRACTIONS.
N,N-Dimethyl-p-(phenylazo)aniline is not known to occur in nature(1).
Release of N,N-dimethyl-p-(phenylazo)aniline to the environment will occur as a result of its manufacture and use as a dye intermediate(1); in photosensitive polymers and reusable films(2); and as an indicator in volumetric analysis, in test for oxidized fat, and as a coloring agent(3).
TERRESTRIAL FATE: If N,N-dimethyl-p(phenylazo)aniline is released to soil it may bind to the soil based on an estimated Koc of 7390 and therefore should not leach to the groundwater. However, since N,N-dimethyl-p-(phenylazo)aniline has a pKa of 3.226(1) at 25 °C, it exists partially as a cation and the extent of its adsorption to soils and sediments should be affected by the pH of the medium. It should not hydrolyze in soils. No information was found on biodegradation in soils(SRC).|AQUATIC FATE: If N,N-dimethyl-p-(phenylazo)aniline is released to water it may bioconcentrate in aquatic organisms, adsorb to sediment and may be subject to direct photolysis. It should not hydrolyze or evaporate from water. Based on a laboratory screening test using an inoculum from settled domestic wastewater, it may be subject to biodegradation. (SRC)|ATMOSPHERIC FATE: If N,N-dimethyl-p-(phenylazo)aniline is released to the atmosphere, it may be subject to direct photolysis and the estimated vapor phase half-life in the atmosphere is 7.04 hrs as a result of photochemically produced hydroxyl radicals adding to the aromatic rings; however, it may exist primarily adsorbed onto particulate matter due to its very low vapor pressure. (SRC)
Based on the stability of aromatic amines(1) and other azobenzene compounds(2), N,N-dimethyl-p-(phenylazo)aniline should not hydrolyze. N,N-dimethyl-p-(phenylazo)aniline strongly absorbs light >290 nm(3); therefore, it may be susceptible to direct photolysis. A rapid, reversible equilibrium occurs between aniline and other primary and secondary aromatic humates or humic analogs followed by addition to quinodal structures and oxidation(4); this may occur with N,N-dimethyl-p-(phenylazo) aniline(SRC). The estimated vapor phase half-life in the atmosphere is 7.04 hrs as a result of photochemically produced hydroxyl radicals adding to the aromatic ring(5); however, due to the very low estimated vapor pressure (3.3X10-7 mm Hg(7)) N,N-dimethyl-p-(phenylazo)aniline may exist in the atmosphere primarily adsorbed onto particulate matter(8). The pKa of N,N-dimethyl-p-(phenylazo)aniline is 3.226 at 25 °C(6) and therefore it exists partially as a cation; this may affect its reactivity in the environment.
Using a reported log octanol/water partition coefficient of 4.58(1), an estimated BCF of 1780 was calculated(2,SRC). Based on this estimated BCF, N,N-dimethyl-p-(phenylazo)aniline should bioconcentrate in aquatic organisms(SRC).
7.41e+03 L/kg|Using a reported log octanol/water partition coefficient of 4.58(1), an estimated Koc of 7390 was calculated(2,SRC). Based on this estimated Koc, N,N-dimethyl-p-(phenylazo)aniline should adsorb to soils and sediment. Since N,N-dimethyl-p-(phenylazo)aniline has a pKa of 3.226 at 25 °C(3), and it exists partially as a cation, the extent of its adsorption to soils and sediments may be affected by the pH of the medium.
Using an estimated vapor pressure of 3.3X10-7 mmHg(1) and water solubility of 13.6 ppm(1), a Henry's Law constant of 7.1X10-9 atm-cu m/mol was calculated(2,SRC). Based on this estimated Henry constant, N,N-dimethyl-p-(phenylazo)aniline should not evaporate from water(2).
Exposure to N,N-dimethyl-p-(phenylazo)aniline may occur as a result of occupational dermal exposure. (SRC)|NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,454 workers are potentially exposed to N,N-dimethyl-(phenylazo)aniline in the USA(1). NIOSH (NOHS Survey 1972-74) has statistically estimated that 2,692 workers are potentially exposed to N,N-dimethyl-p-(phenylazo)aniline in the USA(2).
Drug Information
Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)|Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)
MORE THAN HALF OF BOUND DYE IN ALL LIVER-CELL FRACTIONS IS ASSOC WITH SOL PROTEINS; OF THIS, 80% IS BOUND TO FRACTION WHICH ACCOUNTS FOR ONLY 15% OF SOL PROTEINS.|BILIARY EXCRETION OF THE AZO DYE CARCINOGEN, N,N-DIMETHYL-4-AMINOAZO(C-14)BENZENE (DAB) WAS STUDIED IN MALE RATS. AFTER A SINGLE IV DOSE OF CARCINOGEN, 20-25% OF THE INJECTED RADIOACTIVITY APPEARS IN THE BILE WITHIN 1 HR, ENTIRELY AS METABOLITES.|IT WAS ADMIN IP TO WISTAR RATS & FOUND TO HAVE THE TENDENCY TO BIND TO LIVER TISSUES, NUCLEI & CHROMATIN WITH SPECIFIC BINDING AFFINITY TO NUCLEAR NONHISTONE PROTEIN.
YIELDS 4'-DIMETHYLAMINO-4-HYDROXYAZOBENZENE & 4-METHYLAMINOAZOBENZENE IN RAT. /FROM TABLE/|DAB IS METABOLIZED VIA FOLLOWING PATHWAYS: 1) REDUCTION & CLEAVAGE OF AZO GROUP; 2) DEMETHYLATION; 3) RING HYDROXYLATION; 4) N-HYDROXYLATION; 5) N-ACETYLATION & O-CONJUGATION OF METABOLITES.|IN RATS & MICE, CARCINOGENIC AROMATIC AZO-DYES UNDERGO N-HYDROXYLATION, & FOR EXAMPLE, N-HYDROXY-N-ACETYL-4-AMINOAZOBENZENE IS URINARY METABOLITE OF HEPATOCARCINOGENIC 4-DIMETHYLAMINOAZOBENZENE ... .|A study was made of the azoreduction of dimethylaminoazobenzene (DAB) in-vitro by purified rat liver NADPH cytochrome p450-reductase and by a partially purified reconstituted cytochrome p450 system. Male Wistar rats were induced with clofibrate, nafenopin, phenobarbital, or beta-naphthoflavone prior to liver microsomal isolation. ... Both purified NADPH cytochrome p450 reductase and the reconstituted system reduced dimethylaminoazobenzene, with a more than five fold greater rate for the latter. A ratio of 2:1 azoreductase to cytochrome p450 was optimal for dimethylaminoazobenzene reduction. Clofibrate was the only inducer of azoreductase. Reaction with the suicide inhibitor 10-undecynoic acid distinguished laurate hydroxylase from the azoreductase. The reconstituted system was active in air and carbon monoxide, while purified NADPH cytochrome p450 reductase was inhibited in air. In both systems, nearly 50 fold acceleration of dimethylaminoazobenzene azoreduction occurred in the presence of flavin adenine dinucleotide or flavin mononucleotide, but only under anaerobic conditions, indicating facilitation of electron flow to dimethylaminoazobenzene onlhy from NADPH cytochrome p450-reductase and not from cytochrome p450 itself. This was confirmed with the use of cytochrome p450 inhibitors. ... There appears to be an obilgatory electron flow through cytochrome p450 to dimethylaminozaobenzene, bypassing an oxygen sensitive step, and dietary riboflavin probably attenuates dimethylaminoazobenzene hepatocarcinogenicity solely by its effect on intestinal bacteria.|For more Metabolism/Metabolites (Complete) data for 4-(DIMETHYLAMINO)AZOBENZENE (7 total), please visit the HSDB record page.
4-Dimethylaminoazobenzene (or butter yellow) has been used as a laboratory hepatocarcinogen to study the mode of action of this class of compounds, including structure activity relationships. Because of its characteristic color change as a function of pH, it was the first carcinogen that demonstrated binding to cellular macromolecules. Because of the flavin-dependent azo dye reductase, it was also one of the first carcinogens with a clear-cut nutritional modulation of its activity. Substitution with polar groups such as sulfonic acid in simple azo dyes usually abolishes carcinogenicity and mutagenicity. Thus, molecules such as FD and C Red No. 2 (amaranth) are not mutagenic or carcinogenic. On the other hand, tetra-azo dyes such as direct black 38 or direct blue 6, which are not mutagenic and are quite polar, can release the mutagenic carcinogenic benzidine upon reduction of the azo link by bacteria. Such dyes are highly carcinogenic.
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.
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)|(See procedures)
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
IN USA, IT WAS WITHDRAWN FROM APPROVED LIST OF FOOD ADDITIVES IN 1918, 6 MO AFTER ITS ADDITION TO LIST, BECAUSE CONTACT DERMATITIS WAS OBSERVED IN UP TO 90% OF FACTORY WORKERS HANDLING IT.|N-DIMETHYL-P-AMINOAZOBENZENE WAS ACTIVE IN INDUCING UNSCHEDULED DNA SYNTHESIS IN HELA HUMAN CERVICAL CANCER CELLS TESTED IN PRESENCE OR ABSENCE OF RAT LIVER MIXED-FUNCTION OXIDASE PREPARATION.|The only occupational health observation in man was of contact dermatitis in factory workers handling /4-(Dimethylamino)azobenzene/.
4 Dimethylaminoazobenzene
The substance can be absorbed into the body by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact
Enlarged liver; liver, kidney disturbance; contact dermatitis; cough, wheezing, dyspnea (breathing difficulty); bloody sputum; bronchial secretions; frequent urination, hematuria (blood in the urine), dysuria; [potential occupational carcinogen]
Cough. Sore throat.
Redness. Pain.
Redness. Pain.
Skin, respiratory system, liver, kidneys, bladder
Solvent Yellow 2 Use and Manufacturing
By diazotization of aniline and sodium nitrite, and then coupled with xylidine. The aniline was slowly added to concentrated hydrochloric acid with crushed ice, and sodium nitrite solution was added at 0-5°C for diazotization reaction. Then add xylidine to the diazonium salt, control the temperature below 5°C, add industrial sodium acetate while stirring, add a small amount of sodium acetate after stirring for 3h, and filter out the yellow precipitate to obtain the crude product. After drying, recrystallize with toluene, and then recrystallize with ethanol to obtain the finished dimethyl yellow.
For determination of free HCl in gastric juice; spot test identification of peroxidized fats; pH indicator (red 2.9, yellow 4.0).
Formerly used as a coloring agent in foods, drugs, and cosmetics
(1978) NOT PRODUCED COMMERCIALLY IN USA|(1982) NOT PRODUCED COMMERCIALLY IN USA
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.
NOT USED COMMERCIALLY IN USA
Benzenamine, N,N-dimethyl-4-(2-phenyldiazenyl)-: ACTIVE|... WAS USED TO GIVE YELLOW COLOR TO HAIR CREAMS IN SCANDINAVIA.|... NOT APPROVED FOR GENERAL FOOD USE IN ANY OF THE COUNTRIES SURVEYED.|... IS NOT USED IN FOODS, DRUGS OR COSMETICS; THUS ITS MFR & TESTING DO NOT CONFORM TO RIGID CHEMICAL SPECIFICATIONS, & ITS COMPOSITION VARIES TO MEET CUSTOMER SHADE & INTENSITY REQUIREMENTS.
DETERMINATION OF SOME CARCINOGENIC AMINOAZOBENZENES BY POLAROGRAPHY.|Analyte: 4-dimethylaminoazobenzene; Matrix: air; Analysis by GC; Range: 4-2000 ug/cu m in a 50 l sample.
SERA FROM RATS BEARING INTRAPERITONEAL IMPLANTS OF AN AMINOAZO DYE-INDUCED HEPATOMA WERE FRACTIONATED BY SEPHADEX G200 & DEAE-CELLULOSE ION EXCHANGE COLUMN CHROMATOGRAPHY AND CHARACTERIZED.
Hazardous Air Pollutants (HAPs)|Health Hazards -> Carcinogens
Computed Properties
Molecular Weight:225.29
XLogP3:4.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:225.126597491
Monoisotopic Mass:225.126597491
Topological Polar Surface Area:28
Heavy Atom Count:17
Complexity:236
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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