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N,N-Dimethyl-p-phenyl-azoanilin
METHYL YELLOW · Dimethylaminoazobenzene · 4-DIMETHYLAMINOAZOBENZENE · DIMETHYL YELLOW · N,N-DIMETHYL-4-(PHENYLAZO)ANILINE · BUTTER YELLOW · Benzenamine, N,N-dimethyl-4-(phenylazo)- · OIL YELLOW
Identifikatoren & physikalische Daten
| CAS No. | 60-11-7 |
|---|---|
| Summenformel | C14H15N3 |
| Durchschnittliche Molmasse | 225,29 g/mol |
| Monoisotopische Masse | 225,12659748 g/mol |
| SMILES | CN(C)c1ccc(N=Nc2ccccc2)cc1 |
| InChIKey | JCYPECIVGRXBMO-UHFFFAOYSA-N |
| PubChem CID | 6053 |
| ChEMBL | CHEMBL1090440 |
| ChEBI | CHEBI:17903 |
| EC No. | 200-455-7 |
| DTXSID | DTXSID5020491 |
| Lokaler Name | N,N-Dimethyl-p-phenyl-azoanilin |
Chemische & physikalische Eigenschaften
| XLogP | 4,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 28 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 236 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)Dyes -> Azo DyesCarcinogens |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | log Kow= 4.584.05 |
| Color/Form | YELLOW CRYSTALLINE LEAFLETSYellow, leaf-shaped crystals. |
| Löslichkeit | less than 1 mg/mL at 72 °F (NTP, 1992)SOL IN ALCOHOL, BENZENE, CHLOROFORMSOL IN ETHER, PETROLEUM ETHER, MINERAL ACIDS, OILS.VERY SOL IN PYRIDINE.Water solubility of 13.6 ppm.Solubility in water: none0.001%Insoluble in watersoluble in ethanol, benzene, ether, chloroform,petroleum ether, mineralacids, oils13.6 mg/L |
| Siedepunkt | Sublimes (NIOSH, 2024)356.8°C (rough estimate) |
| Schmelzpunkt | 232 °F (decomposes) (NTP, 1992)114-117 °C237 °F111 °C (dec.)(lit.) |
| Dampfdichte | 7.78 (NTP, 1992) - Heavier than airwill sink (Relative to Air) |
| Dampfdruck | 3e-07 mmHg (est.) (NIOSH, 2024)0.0000003 [mmHg]0.0000003 mmHg (est.)3 x 10-7 mmHg (estimated, NIOSH, 1997) |
| Henry-Konstante | Henry's Law constant= 7.1X10-9 atm-cu m/mol (calculated).1.4×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Physical Description | 4-dimethylaminoazobenzene appears as yellow crystalline leaflets or an orange powder. (NTP, 1992)Yellow, leaf-shaped crystals[NIOSH]YELLOW CRYSTALS.Yellow, leaf-shaped crystals. |
| Dichte | 1.1303 (rough estimate) |
| Brechungsindex | 1.5770 (estimate) |
| Lagerbedingungen | Store at RT. |
| pKa (Säurekonstante) | 3.226(at 25℃) |
| Aggregatzustand | Powder |
| Farbe | Yellow |
| pH | 2.9-4.0 |
| Merck | 14,3229 |
| BRN | 746016 |
| Stabilität | Stable, but heat and light sensitive. Incompatible with strong oxidizing agents, strong acids. |
| Hauptanwendungen | Electrochromic materials, sol-gel coatings, display device, inks, gasdetection apparatus, status assessment indetection apparatus, nematocides, hair dyes, diapers, food storage, status assessment inbreast cancer, detecting carbohydrates, bacteria, diagnosing cervical disease, wound dressing materials |
| InChI | 1S/C14H15N3/c1-17(2)14-10-8-13(9-11-14)16-15-12-6-4-3-5-7-12/h3-11H,1-2H3 |
| InChIKey | JCYPECIVGRXBMO-UHFFFAOYSA-N |
| SMILES | CN(C)c1ccc(cc1)N=Nc2ccccc2 |
| CAS Datenbank | 60-11-7(CAS DataBase Reference) |
| NIST chemische Informationen | Benzenamine, N,N-dimethyl-4-(phenylazo)-(60-11-7) |
| EPA chemische Informationen | 4-Dimethylaminoazobenzene (60-11-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 52 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.WarningH315: Causes skin irritation [Warning Skin corrosion/irritation] |
|---|---|
| Regulatorische Informationen | Chemical: Benzenamine, N,N-dimethyl-4-(phenylazo)-Hazard Traits - CarcinogenicityDermatotoxicityRegulation (EC) No 178/2002 (amended)C.I. Solvent Yellow 2: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzenamine, N,N-dimethyl-4-(phenylazo)-: Environment tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)Not combustible. |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for 4-Dimethylaminoazobenzene: |
| Gefahrenübersicht | 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.In animal studies: liver injuryIn feeding studies of dogs: bladder cancer[HSDB] |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: III |
| Special Reports | 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. |
| RCRA-Anforderungen | U093As 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). |
| Reactivity Alerts | Explosive |
| OSHA Standards | 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. |
| Brandbekämpfung | 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. |
| Erste-Hilfe-Maßnahmen | 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.Give one or two glasses of water to drink. |
| Erste Hilfe | 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.(General first aid procedures) |
| Lagerbedingungen | PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... . Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/ |
| Reinigungsverfahren | 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/ |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | 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. |
| Verschüttetes entsorgen | 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. |
| Preventive Measures | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection. |
| Inhalation Risk | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly when dispersed. |
| Cancer Sites | [in animals: liver & bladder tumors] |
| Wechselwirkungen | DIETS HIGH IN RIBOFLAVIN OR SUPPLEMENTED WITH POLYCYCLIC HYDROCARBONS, WHICH REDUCED TUMOR INDUCTION BY AZO DYES, ALSO LOWERED BINDING OF DYES TO PROTEIN FRACTIONS. |
| Zielorgane | Skin, respiratory system, liver, kidneys, bladder |
| Umweltverhalten | 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 ringshowever, it may exist primarily adsorbed onto particulate matter due to its very low vapor pressure. (SRC) |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | The substance can be absorbed into the body by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Sore throat.Redness. Pain.Enlarged liverliver, kidney disturbancecontact dermatitiscough, wheezing, dyspnea (breathing difficulty)bloody sputumbronchial secretionsfrequent urination, hematuria (blood in the urine), dysuria[potential occupational carcinogen] |
| ICSC Environmental Data | Environmental effects from the substance have not been investigated adequately. |
| Medical Surveillance | Employment & periodical examinations should focus on liver function.PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/ |
| Soil Adsorption/Mobility | 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. |
| Natural Pollution Sources | N,N-Dimethyl-p-(phenylazo)aniline is not known to occur in nature(1). |
| Human Toxicity Excerpts | 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/. |
| Luftstandards | 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. |
| CERCLA-Meldepflichtmengen | 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) 424-8802In 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). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29270000 |
| RTECS-Nr. | BX7350000 |
| R-Sätze (R) | 25-40-68-45-23/24/25 |
| Toxizität | Acute oral LD50 for mice 300 mg/kg, rats 200 mg/kg (quoted, RTECS, 1985). |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 36/37-45-53-22 |
| Gefahrenklasse | 6.1Acute Tox. 3 OralCarc. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 60-11-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
4-N,N-Dimethylaminobenzene diazonium chloride is a diazo compound found in diazo copy paper. It is allergenic only when unexposed.
Verwenden
For determination of free HCl in gastric juice; spot test identification of peroxidized fats; pH indicator (red 2.9, yellow 4.0).
Herstellung & Synthese
synthetische
aniline diazotization, and N,N-dimethylaniline coupling.