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3,3'-Dimethyl-benzidin
DMB · Tolidine · 3,3'-DIMETHYLBENZIDINE · DIMETHYLBENZIDINE · ORTHO TOLIDINE · 3,3'-DIMETHYL-4,4'-DIAMINOBIPHENYL · 3,3'-Dimethylbiphenyl-4,4'-diamine · 2-Tolidine
Identifikatoren & physikalische Daten
| CAS No. | 119-93-7 |
|---|---|
| Summenformel | C14H16N2 |
| Durchschnittliche Molmasse | 212,29 g/mol |
| Monoisotopische Masse | 212,13134851 g/mol |
| SMILES | Cc1cc(-c2ccc(N)c(C)c2)ccc1N |
| InChIKey | NUIURNJTPRWVAP-UHFFFAOYSA-N |
| PubChem CID | 8413 |
| ChEMBL | CHEMBL85109 |
| ChEBI | CHEBI:34320 |
| EC No. | 204-358-0 |
| DTXSID | DTXSID5024059 |
| Lokaler Name | 3,3'-Dimethyl-benzidin |
Chemische & physikalische Eigenschaften
| XLogP | 2,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 52 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 205 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)Nitrogen Compounds -> Benzidine and DerivativesCarcinogens |
| SpringerMaterials Properties | Crystal structure |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | log Kow = 2.34 |
| Dichte | 1 (NTP, 1992)1.234 g/cu cm1.2 g/cm³0.9678 (rough estimate) |
| Color/Form | Colorlessin technical grades also brownish flakesWhite to reddish crystals or powder [Note: Darkens on exposure to air] |
| Löslichkeit | less than 1 mg/mL at 66 °F (NTP, 1992)In water, 1,300 mg/L at 25 °CSoluble in alcohol, ether, dilute acidsSolubility in water, g/100ml at 25 °C: 0.13 (poor)0.1%2% HCl: 10 mg/mL, clearSlightly soluble in water. |
| Flammpunkt | 137 °C244 °C471 °F |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 392 °F at 760 mmHg (NTP, 1992)300 °C300 °C @760 [mm Hg]572 °F300.5 °C |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 264 to 268 °F (NTP, 1992)129-131 °CMP: 264 °F131-132 °C128-131 °C(lit.) |
| Brechungsindex | n20/D 1.341 |
| Lagerbedingungen | -20°C |
| Aggregatzustand | powder (may contain lumps) |
| pKa (Säurekonstante) | 4.59±0.10(Predicted) |
| Farbe | light brown |
| Merck | 14,9514 |
| BRN | 2210640 |
| Henry-Konstante | 1.6×105 mol/(m3Pa) at 25℃, HSDB (2015) |
| Hauptanwendungen | diagnostic assay manufacturinghematologyhistology |
| InChI | 1S/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3 |
| InChIKey | NUIURNJTPRWVAP-UHFFFAOYSA-N |
| SMILES | Cc1cc(ccc1N)-c2ccc(N)c(C)c2 |
| NIST chemische Informationen | [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dimethyl-(119-93-7) |
| EPA chemische Informationen | 3,3'-Dimethylbenzidine (119-93-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dimethyl-Hazard Traits - CarcinogenicityRespiratory Toxicity[1,1'-Biphenyl]-4,4'-diamine, 3,3'-dimethyl-: HSNO Approval: HSR001543 Approved with controlsThe 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 - [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dimethyl-: Environment tier I assessment |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for o-Tolidine: |
| Gefahrenübersicht | 3,3'-Dimethylbenzidine is used as an intermediate in the production of dyes and pigments. Acute (short- term) exposure to high levels of 3,3'-dimethylbenzidine in humans may irritate the nose and throat. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of 3,3'-dimethylbenzidine in humans. A study by the National Toxicology Program (NTP) reported that oral exposure to 3,3'-dimethylbenzidine dihydrochloride resulted in an increased incidence of tumors of the skin, liver, intestine, lung, and other organs. EPA has classified 3,3'-dimethylbenzidine as a Group B2, probable human carcinogen.A carcinogen in experimental animals[HSDB] In subchronic feeding studies, animals develop liver and kidney damage and bone marrow depression. [ACGIH] See Benzidine. |
| Reaktive Gruppe | Amines, Aromatic |
| EG-Einstufung | Symbol: T, NR: 45-22-51/53S: 53-45-61Note: E |
| Special Reports | U.S. Department of Health & Human Services/National Toxicology ProgramTwelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 3,3'-Dimethylbenzidine (119-93-7) was first listed in the Third Annual Report on Carcinogens (1983) as reasonably anticipated to be a human carcinogen and re-reviewed in the Tenth Report on Carinogens (2002). /3,3'-Dimethylbenzidine and Dyes Metabolized to 3,3'-Dimethylbenzidine/[Available from, as of July 17, 2013: http://ntp.niehs.nih.gov/]Health hazard alert: benzidine-, o-tolidine-, & o-dianisidine-based dyesdhhs (niosh) publ usa (81-106) 39 pp (1980). A review with 42 references on the health hazard of benzidine, o-tolidine, & o-dianisidine dyes & 118 dyes based on these cmpd.USEPAHealth and Environmental Effects Profile for 3,3'-DimethylbenzidineEnvironmental Criteria and Assessment Office, Cincinnati, OH, EPA/600/X-87/391 (1987), NTIS PB89-119929DHHS/NTPToxicology & Carcinogenesis Studies of 3,3'-Dimethylbenzidine Dihydrochloride in F344/N Rats (Drinking Water Studies) Technical Report Series No. 390 (1991) NIH Publication No. 91-2845 |
| RCRA-Anforderungen | U095As stipulated in 40 CFR 261.33, when 3,3'-dimethylbenzidine, 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 Profile | 3,3'-DIMETHYLBENZIDINE is sensitive to exposure to light. May be sensitive to prolonged exposure to air. A weak base that forms salts with hydrochloric acid or sulfuric acid. It can be acetylated. Incompatible with strong agents (NTP, 1992). |
| 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. 3,3'-Dimethylbenzidine is included on this list. |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes including nitrogen oxides. Reacts with oxidants. |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use powder, water spray, foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.Rinse with plenty of water (remove contact lenses if easily possible).Rinse mouth. 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) |
| Sichere Lagerung | Separated from strong oxidants and food and feedstuffs. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. |
| Brandbekämpfungsverfahren | Use powder, water spray, foam, carbon dioxide. |
| Lagerbedingungen | Separated from strong oxidants and food and feedstuffs. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.... Protected from light.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 | A new method developed for the removal of carcinogenic aromatic amines from industrial aqueous effluents uses horseradish peroxidase & hydrogen peroxide resulting in a nearly complete precipitation of carcinogenic aromatic amines from water due to enzymatic crosslinking.Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.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/ |
| 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 U095, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A good 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 good 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.It is shown that the oxidation of benzidine, o-tolidine, and o-dianisidine with potassium permanganate in a sulfuric acid medium results in a deep destruction of these substances in which more than 99.8% of the original compounds is destroyed.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/For more Disposal Methods (Complete) data for 3,3'-DIMETHYLBENZIDINE (11 total), please visit the HSDB record page. |
| Verschüttetes entsorgen | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | 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 3,3'-DIMETHYLBENZIDINE (16 total), please visit the HSDB record page. |
| Eye Prevention | Wear safety spectacles. |
| Cancer Sites | [in animals: liver, bladder & mammary gland tumors] |
| Wechselwirkungen | ... Elevated risk for cancer of the urinary bladder has been found in workers employed in dye manufacture, and those exposted to combination of benzidine and o-Tolidine...There is some evidence that concurrent exposure to o-tolidine decreased the time to appearance of tumors in rats treated with benzidine. |
| Zielorgane | Eyes, respiratory system, liver, kidneys |
| Ökotoxizitätswerte | EC50Species: Daphnia magna (Water Flea)Conditions: freshwater, renewal, 25 °C, pH >7Concentration: 3200 ug/L for 24 hrEffect: behavior, equilibrium /formulation/Species: Daphnia magna (Water Flea) age < or =24 hrConditions: freshwater, static, 25 °C, pH > or =7, dissolved oxygen > or =58%Effect: intoxication, immobilization /formulation/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3190(SRC), determined from a structure estimation method(2), indicates that 3,3'-dimethylbenzidine is expected to have slight mobility in soil(SRC). The pKa values of 3,3'-dimethylbenzidine are 4.50 and 3.3(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). In sediment studies, sorption measurements over the pH range of 5 to 9 saw an increase in sorption as the pH decreased suggesting that the protonated form of 3,3'-dimethylbenzidine was more strongly bound than the neutral form(5). Volatilization of 3,3'-dimethylbenzidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 3,3'-Dimethylbenzidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). 3,3'-Dimethylbenzidine, present at 100 mg/L, reached 3% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(6), indicating the compound is not readily biodegradable(6). 3,3'-Dimethylbenzidine absorbs light >290 nm(7) and may be susceptible to direct photolysis by sunlight on soil surfaces(SRC). Benzidine is rapidly oxidized by Fe(III) and several other cations which are frequently found in environmental soils and clays(8) which suggest that 3,3'-dimethylbenzidine may also be degraded by a similar process(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3190(SRC), determined from a structure estimation method(2), indicates that 3,3'-dimethylbenzidine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.3X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(7), BCF values in the range of 4.8 to 83(4), measured in carp (Cyprinus carpio), suggest bioconcentration in aquatic organisms is low to moderate(SRC). 3,3'-Dimethylbenzidine, present at 100 mg/L, reached 3% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(6), indicating the compound is not readily biodegradable(5). 3,3'-Dimethylbenzidine absorbs light >290 nm(6) and may be susceptible to direct photolysis. When aerated solutions of benzidine were exposed to a light from a xenon lamp (300-400 nm) complete degradation of benzidine was observed in 12 hours(7)photodegradation of 3,3'-dimethylbenzidine may be similar(SRC). Aromatic amines are susceptible to photooxidation in natural waters via reaction with OH and RO2 radicals with half-lives on the order of a few days or less(8), therefore, photooxidation may be an important fate process for 3,3'-dimethylbenzidine in sunlit natural water(SRC). Benzidine is rapidly oxidized by Fe(III) and several other cations which are frequently found in environmental soils and clays(9) which suggests that 3,3'-dimethylbenzidine may also be degraded by a similar process(SRC). 3,3'-Dimethylbenzidine is not expected to undergo hydrolysis due to a lack of hydrolyzable functional groups(3).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,3'-dimethylbenzidine, which has an estimated vapor pressure of 1.0X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3,3'-dimethylbenzidine 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 2 hours(SRC), calculated from its rate constant of 1.9X10-10 cu cm/molecule-sec at 25 °C (SRC)determined using a structure estimation method(2). 3,3'-Dimethylbenzidine absorbs light >290 nm(3), therefore, it may be susceptible to direct photolysis(SRC). Particulate-phase 3,3'-dimethylbenzidine may be removed from the air by wet and dry deposition(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 through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Signs and Symptoms | MAY BE ABSORBED! See EFFECTS OF LONG-TERM OR REPEATED EXPOSURE.irritation eyes, noseIn Animals: liver, kidney damage[potential occupational carcinogen] |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of July 18, 2013: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=119-93-7]The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. /3,3'-Dimethylbenzidine dihydrochloride/[Available from, as of July 18, 2013: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=612-82-8] |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment. |
| EPA IRIS Information | 3,3-Dimethylbenzidine |
| Medical Surveillance | 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/ |
| 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) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| Landesrichtlinien für Trinkwasser | (FL) FLORIDA 250 ug/L |
| F | 8 |
| Arbeitsplatzgrenzwert (OEL) | Ceiling: 0.02 mg/m3 [60-minute] [skin] |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3082 9/PG 3 |
| Zollcode | 29215900 |
| RTECS-Nr. | DD1225000 |
| R-Sätze (R) | 45-68-51/53-22-11 |
| Toxizität | dog,LDLo,oral,600mg/kg (600mg/kg),Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 58, Pg. 167, 1907. |
| Gefahrensymbole | T,N,F |
| Sicherheitshinweise (S) | 53-45-61-16 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 OralAquatic Chronic 2Carc. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 119-93-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
o-Tolidine, also called orthotolidine or 2-tolidine, is a chemical compound with the molecular formula (C6H4(CH3)NH2)2. It is a white to reddish-colored, combustible, aromatic amine that emits toxic fumes of nitrogen oxides when heated to decomposition. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as hydrochloride, which is commercially available. 2-Tolidine can be produced by a benzidine rearrangement from a hydrazine derivative derived from 2-nitrotoluene.
Verwenden
o-Tolidine is used extensively in the manufacture of dyes, especially in the production of soluble azo dyes and insoluble pigments for the textile, leather, and paper sectors. Additionally, It is also used as a sensitive colorimetric reagent for the analysis of gold and free chlorine in water.
Herstellung & Synthese
synthetische
There are two commonly used methods for producing o-Tolidine. The first method involves reducing ortho-nitrotoluene to 1,2-diorthotolylhydrazine, which is then rearranged with acid. The second method involves reducing o-nitrotoluene using zinc dust and caustic soda, then converting the resulting hydrazotoluene to o-Tolidine by boiling it with hydrochloric acid. Once either of these methods is completed, o-Tolidine can be extracted and purified through techniques such as solvent extraction and recrystallization.