Azobenzene
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Azobenzene
structure -
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CAS No:
103-33-3
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Formula:
C12H10N2
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Chemical Name:
Azobenzene
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Synonyms:
Diazene,1,2-diphenyl-;Azobenzene;Diazene,diphenyl-;Benzene,azo-;1,2-Diphenyldiazene;Azobenzide;Azobenzol;Benzeneazobenzene;Diphenyldiimide;Benzene,azobis-;Diphenyldiazene;Phenylazobenzene;A 15073;NSC 2102
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CAS No:
Description
orange to red crystals Azobenzene is a combustible, orange-red crystalline solid.ChEBI: A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.Orange-red crystals or dark brown chunky solid.
Azobenzene appears as orange-red crystals or dark brown chunky solid. (NTP, 1992)
Azobenzene appears as orange-red crystals or dark brown chunky solid. (NTP, 1992)|Azobenzene is a molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.
Azobenzene Basic Attributes
182.22
182.22
203-102-5
F0U1H6UG5C
2102
DTXSID8020123
Orange-red leaflets|Monoclinic crystals|Yellow or orange crystals
29270000
Characteristics
24.7
3.82
Orange Crystalline Powder
1.203 g/cm3 @ Temp: 20 °C
68 °C
293 °C
100 °C
1.62662 (78.1℃)
soluble in alcohol, ether, benzene and glacial acetic acid. Insoluble in water.
2-8°C
1 mm Hg ( 104 °C)
Oral-rat LD50: 1000 mg/kg; intraperitoneal-mouse LD50: 500 mg/kg
Combustion produces toxic nitrogen oxide gas
Henry's Law constant = 1.35X10-5 atm-cu m/mole at 25 °C (est)
pKa = -2.950E+00
Combustible|MW = 182.220, orange-red plates (petroleum ether), MP = 71, soluble in ethanol, ether, benzene, acetic acid, and ligroin /Cis/|Hydroxyl radical reaction rate constant = 1.55X10-12 cu cm/molec-sec at 25 °C (est)
This chemical is sensitive to air and light. Dust may form an explosive mixture in air. Insoluble in water.
Azo, Diazo, Azido, Hydrazine, and Azide Compounds
AZOBENZENE is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class 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. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. This compound is incompatible with strong oxidizing agents. (NTP, 1992)
Safety Information
III
6.1(b)
UN 3077 9/PG 3
3
45-20/22-48/22-50/53-68-67-65-62-51/53-38-11-48/20-39/23/24/25-23/24/25-52/53
53-45-60-61-62-36/37-33-29-16-9-7
CN1400000
T,N,Xn,F
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sensitive.
P201-P273-P281-P308 + P313-P501
H302 + H332-H341-H350-H373-H410
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|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/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for AZOBENZENE (6 total), please visit the HSDB record page.
Strong oxidizers.
DHEW/NCI; Bioassay of Azobenzene for Possible Carcinogenicity (1979) Technical Rpt Series No. 154 DHEW Pub No. (NIH) 79-1710
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P281, P301+P312, P304+P312, P304+P340, P308+P313, P312, P314, P330, P391, P405, and P501|H302+H332 (37.11%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]|Aggregated GHS information provided by 97 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501
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 chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing material for your operation. All protective clothing (suits, gloves, footwear, headgear) should be clean, available for work each day, and put on before work. Contact lenses should not be worn when working with this chemical. Wear dust-proof chemical goggles and face shield unless full face-piece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.|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/
Use dry chemical, carbon dioxide, or alcohol foam extinguishers. Poisonous gases are produced in fire including nitrogen oxides. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are required to fight fires, they must be properly trained and equipped. OSHA 1910.156.
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 bag 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 bag, 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/
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/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for AZOBENZENE (9 total), please visit the HSDB record page.
PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/|No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
... Irritates the eyes, skin, and respiratory tract.
Azobenzene has been detected at levels as high as 123 ug/L in industrial wastewater effluents from automotive cleaning operations and other (unspecified) industrial laundering processes(1). An azobenzene concn of 0.03 ppm was detected in wastewater effluent in one sample collected from an unnamed specialty chemical manufacturing plant(2).
SEDIMENT: Azobenzene was detected in sediments of the Huaihe River, China at 6 different sampling sites with concns ranging from 0.13-0.29 mg/kg. Samples were taken from Xiao Zui, Huaihe Bridge, and Hongguang Chemical Plant during the summer of 2002. The samples were filtered on an SPE-filtration device and analyzed using gas chromatography and mass spectrometry(1). The U.S. Geological Survey's National Water-Quality Assessment (NAWQA) study detected azobenzene, along with other semi-volatile organic chemicals, at 0.4% of 492 sites and detected at a maximum concn of 130 ug/kg dry weight in streambed sediments. The survey conducted testing from across 536 streambed sites in 20 major river basin systems across the U.S. during 1992-1995(2).
Toxicity
moderately toxic
A bioassay of azobenzene for possible carcinogenicity was conducted by administering the test chemical in feed to F344 rats and B6C3F1 mice. Groups of 50 rats of each sex were administered azobenzene at one of two doses, either 200 or 400 ppm, for 105 or 106 weeks. Matched controls consisted of 20 untreated rats of each sex. All surviving rats were killed at the end of administration of the test chemical. Groups of 50 male mice were administered azobenzene at one of two doses, either 200 or 400 ppm, for 105 weeks. Groups of 50 female mice were administered the test chemical at one of two doses, initially 400 or 800 ppm, for 38 weeks. Because of excessively lowered body weights in the dosed groups of the females, doses for the females were then reduced to 100 and 400 ppm, respectively, and administration at the lowered doses was continued for 67 or 68 weeks. The time-weighted average doses for the female mice were either 208 or 545 ppm. Matched controls consisted of 20 untreated mice of each sex. All surviving mice were killed at the end of administration of the test chemical. Mean body weights of dosed rats and mice of each sex were lower than those of corresponding controls, and were generally dose related throughout the bioassay. Mortality was dose related in the male rats and the female mice, but was not significantly affected in either the female rats or the male mice. Survival was 70% or greater at week 90 on study in all dosed and control groups of each species and sex; thus, sufficient numbers of animals were at risk in all groups for the development of late-appearing tumors. In rats, a large number of sarcomas, including fibrosarcomas, hemangiosarcomas, and osteosarcomas in both males and females and malignant hemangiopericytomas in females, occurred in the spleen and other abdominal organs at incidences that were dose related in each sex (P<0.001) and that in direct comparisons were significantly higher (P<0.001) in the high-dose groups of each sex than in the corresponding control groups (males: controls, 0/20, low-dose 6/49, high-dose 31/49; females: controls 0/20, low-dose 5/50, high-dose 21/50). In mice, no tumors occurred in either males or females at incidences that were significantly higher in the dosed groups than in the corresponding control groups. It is concluded that under the conditions of this bioassay, azobenzene was carcinogenic (sarcomagenic) for F344 rats, inducing various types of sarcomas in the spleen and other abdominal organs of both males and females. The test chemical was not carcinogenic for B6C3F1 mice of either sex.
Azobenzene is not known to occur in nature(1).
Azobenzene's former production and use an intermediate in the production of dyes and rubber accelerators(1), benzidine and its salts, insecticides and pyrazolone derivatives(2) may have resulted in its release to the environment through various waste streams(SRC). Its former use as a greenhouse fumigant(3) and arcaricide(2) resulted in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values of 1,350-4,510(2,3), indicate that azobenzene is expected to have low to slight mobility in soil(SRC). Volatilization of azobenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 3.61X10-4 mm Hg(4), and water solubility, 6.40 mg/L(5). Azobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Azobenzene was found to be resistant to biodegradation when tested using a Warburg respirometer(6), suggesting that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), experimental Koc values of 1,350-4,510(2,3), indicates that azobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.4X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 3.61X10-4 mm Hg(4), and water solubility, 6.40 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.5 days and 32 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 12 to 22 months if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 10(SRC), from its log Kow of 3.82(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Azobenzene was found to be resistant to biodegradation when tested using a Warburg respirometer(10), suggesting that biodegradation is not an important environmental fate process in soil(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), azobenezene, which has a vapor pressure of 3.61X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase azobenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 days(SRC), calculated from its rate constant of 1.55X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). In methanol, azobenzene will absorb UV light strongly above 290 nm(4), and therefore may be susceptible to direct photolyis by sunlight(SRC).
The rate constant for the vapor-phase reaction of azobenzene with photochemically-produced hydroxyl radicals has been estimated as 1.6X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Azobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Azobenzene, in methanol solution, absorbs UV light strongly in the environmental spectrum above 290 nm(3) which indicates a potential for direct photolysis in sunlight(SRC). Laboratory irradiation (via mercury vapor lamps) of azobenzene in cyclohexane solutions in pyrex flasks (which filters UV light below 290 nm) resulted in azobenzene photodecomposition(4); about 100 hr of irradiation were required for 0.001M solutions to achieve complete decomposition(4); initial photodecomposition products were identified as phenylazo, phenylazomethylene and aniline radicals(3).|Results of degradation studies in an anaerobic sediment/water system indicated that some biodegradation occurs, although abiotic degradation may be faster(1); in a non-sterilized system, a half-life of 13.8 hr was observed, while systems chemically sterilized (via formaldehyde, sodium azide or m-cresol), half-lives of 15.2 to 24.4 hr were observed(1); in an autoclaved system, the half-life jumped to 163 hr, but it was thought that the heating destroyed the chemical agent responsible for the abiotic reduction(1).
An estimated BCF of 10 was calculated for azobenzene(SRC), using a log Kow of 3.82(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
2.00e+03 L/kg|A Koc value of approximately 1,350 was experimentally derived for a silt loam soil(1). Respective Koc values of 2,410 and 4,510 were experimentally determined for a Hagerstown clay loam soil and a Palouse silt loam soil under non-sterile conditions(2); in sterilized soil, respective Koc values of 2,100 and 3,740 were determined(2). According to a suggested classification scheme(3), these Koc values suggest that azobenzene has low to slight mobility in soil(SRC).
The Henry's Law constant for azobenzene is estimated as 1.4X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 3.61X10-4 mm Hg(1), and water solubility, 6.40 mg/L(2). This Henry's Law constant indicates that azobenzene is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2.5 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 32 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 22 months to 370 days if adsorption is considered(4). Azobenzene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Azobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.61X10-4 mm Hg(1).
Occupational exposure and general population exposure due to its use as an arcaricide and fumigant should be low or non-existent since azobenzene is no longer produced or used in the US(SRC). In the past, azobenzene was used as a fumigant in greenhouses against insects and mites and their eggs(1).
Drug Information
4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).
Of 500 mg/kg bw azobenzene given to rabbits, 30% appears in feces; of absorbed azobenzene, /23%/... is excreted in urine... unchanged...|Azobenzene binds to bovine serum albumin. The interaction of azobenzene and other azo compounds with proteins involves secondary valences.
Following administration of azobenzene by ip injection to rats, aniline and water-soluble compound that gives benzidine on acidification were found in urine...|Metabolic pathways catalyzed by liver microsomal enzymes. Azobenzene reduced to aniline. /from table/|Some is also excreted unchanged in urine, but major fraction is present in urine as metabolites hydrazobenzene, benzidine, o- and p-hydroxyazobenzenes, o- and p-aminophenols and their conjugates.|Factors affecting the metabolism of azo compounds in vitro have been studied and conditions which allow maximal metabolism established. A species difference in the extent of N-oxidation was evident, the order of activity depending on the class of substrate used. With the bisaryl azo compound, the order of activity was rabbit > hamster > mouse > guinea pig > rat, while for the bisalkyl and mixed alkyl-aryl azo compounds, the order was hamster > guinea pig > mouse > rabbit > rat. The appropriate kinetic factors, Km and Vmax for the N-oxidation of azobenzene are reported. A sex difference in azobenzene N-oxidase activity was observed in rats but not in hamsters.|For more Metabolism/Metabolites (Complete) data for AZOBENZENE (6 total), please visit the HSDB record page.
SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and respiratory tract; liver and kidney damage; liver and lung cancer; and possible blood disorders. Symptoms of exposure to nitrogen compounds may include cyanosis, headache, shallow respiration, dizziness, confusion, jaundice, pain on urination, anemia, weight loss, weakness, irritability, blood pressure fall, lethargy, stupor, convulsions, coma, and possible death. The nervous system, liver, kidneys, and bone marrow may be affected after chronic exposure. ACUTE/CHRONIC HAZARDS: This compound irritates the skin, eyes, and respiratory tract, and can be absorbed through the skin. It is a positive animal carcinogen. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, and nitrogen oxides. (NTP, 1992)|Carcinogens
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)
Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/
/CASE REPORTS/ A 19 yr old boy ingested 50 mL of Asomite, a mixture of azobenzene and Aramite. Symptoms first appeared after 19 hr and included jaundice and sporadic unconsciousness. Hepatic coma occurred after 4 days and death from "cardiac insufficiency" after 6 days.
azobenzene
Azobenzene Use and Manufacturing
From nitrobenzene according to the following reaction. The nitrobenzene, methanol and sodium hydroxide solution were heated and maintained at 76°C, and zinc powder was slowly added under stirring, and the heat was kept stirring for 16h; then, the zinc powder was added to keep warm for 48h. Filter while hot, cool, add 20% hydrochloric acid to the crude product to dissolve at 70 ℃, cool and filter, heat the crystals in a water bath at 70-80 ℃, let cool filter, and finally recrystallize with ethanol and dry.
Precursor for dyes, for polymers.
FOR VOLATILIZATION FROM HOT WATER PIPES OF GREENHOUSE; 70% IN SUITABLE PASTE; ALSO IN PYROTECHNIC MIXTURE FOR IGNITION (45%). FOR SPRAY APPLICATION: MISCIBLE LIQ OR WETTABLE POWDERS.
Diazene, 1,2-diphenyl-: ACTIVE|AZOBENZENE FORMATION OCCURS BY REACTION OF NITROSOBENZENE WITH AROMATIC AMINE, OR BY CONVERSION FROM HYDRAZOBENZENE FORMED BY CONDENSATION OF AROMATIC AMINE WITH HYDROXYLAMINE, OR REDUCTION OF AZOXYBENZENE. .../SIMILAR/ TO CERTAIN CARCINOGENIC COMPD.|PRODUCT DISCONTINUED FOR PESTICIDE USE BY EASTERN CHEMICAL DIV, GUARDIAN CHEMICAL CORP|...AZOBENZENE, MAY KILL INSECTS BY VAPOR ACTION UNDER CERTAIN CIRCUMSTANCES, & THEIR FUMIGANT ACTION MAY BE ENHANCED THROUGH ATOMIZATION, VOLATILIZATION BY HEATING, OR THROUGH BURNING IN PYROTECHNIC MIXTURES.
POLAROGRAPHIC PROCEDURE CAN BE USED FOR THE QUANTITATIVE ANALYSIS OF ALL THE AMINOAZOBENZENES TESTED IN THIS STUDY AS INDICATED BY PROPORTIONALITY BETWEEN DIFFUSION CURRENT & CONCN.|AZOBENZOL WAS DETERMINED BY GAS CHROMATOGRAPHY AFTER ISOLATION FROM A CARAGARD MIXTURE WHICH WAS EXTRACTED FROM SOIL, GRAPE JUICE & GRAPES.|DETERMINATION OF AZOBENZENE BY HIGH PRESSURE LIQ CHROMATOGRAPHY.|HIGH-PRESSURE LIQUID CHROMATOGRAPHY COUPLED WITH SPECTROPHOTOMETRIC OR AMPHOTERIC MONITORING OF COLUMN EFFLUENTS.|For more Analytic Laboratory Methods (Complete) data for AZOBENZENE (6 total), please visit the HSDB record page.
Health Hazards -> Carcinogens|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Computed Properties
Molecular Weight:182.22
XLogP3:3.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:182.084398327
Monoisotopic Mass:182.084398327
Topological Polar Surface Area:24.7
Heavy Atom Count:14
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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