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3,3',5,5'-Tetramethylbenzidin
TMB · 3,3',5,5'-Tetramethylbenzidine · Tmbz · TMB SUBSTRATE · Tetramethylbenzidine (TMB) · 3,3',5',5-TETRAMETHYLBENZIDINE · 3,3,5,5-TETRAMETHYLBENZIDINE, STANDARD F OR GC · 4-(4-Amino-3,5-dimethylphenyl)-2,6-dimethylaniline
Identifikatoren & physikalische Daten
| CAS No. | 54827-17-7 |
|---|---|
| Summenformel | C16H20N2 |
| Durchschnittliche Molmasse | 240,34 g/mol |
| Monoisotopische Masse | 240,16264864 g/mol |
| SMILES | Cc1cc(-c2cc(C)c(N)c(C)c2)cc(C)c1N |
| InChIKey | UAIUNKRWKOVEES-UHFFFAOYSA-N |
| PubChem CID | 41206 |
| ChEMBL | CHEMBL1331128 |
| EC No. | 259-364-6 |
| DTXSID | DTXSID5026120 |
| Lokaler Name | 3,3',5,5'-Tetramethylbenzidin |
Chemische & physikalische Eigenschaften
| XLogP | 3,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 52 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 226 |
| Stoffklassen | Nitrogen Compounds -> Benzidine and Derivatives |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)Slightly soluble. <0.1 g/100 mL at 20°C.Slightly soluble. <0.1 g/100 mL at 20 ºC |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomp it emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 334 to 336 °F (NTP, 1992)168.5 °C168-171 °C(lit.) |
| Dampfdruck | 0.0000005 [mmHg] |
| Physical Description | 3,3',5,5'-tetramethylbenzidine appears as pale yellow crystals or off-white powder. (NTP, 1992)Pale yellow or off-white solid[CAMEO] White or light yellow solid[MSDSonline] |
| Collision Cross Section | 175.7 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID5026120] |
| Siedepunkt | 100 °C |
| Dichte | 1 |
| Brechungsindex | 1.5519 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 4.49±0.10(Predicted) |
| Aggregatzustand | tablet |
| Farbe | Cream |
| BRN | 2808541 |
| Henry-Konstante | 1.3×105 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable, but moisture sensitive and may be light sensitive. Incompatible with water, strong oxidizing agents. |
| InChI | 1S/C16H20N2/c1-9-5-13(6-10(2)15(9)17)14-7-11(3)16(18)12(4)8-14/h5-8H,17-18H2,1-4H3 |
| InChIKey | UAIUNKRWKOVEES-UHFFFAOYSA-N |
| SMILES | Cc1cc(cc(C)c1N)-c2cc(C)c(N)c(C)c2 |
| CAS Datenbank | 54827-17-7(CAS DataBase Reference) |
| EPA chemische Informationen | 3,3',5,5'-Tetramethylbenzidine (54827-17-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.8% (2 of 72) of reports.WarningH302 (29.2%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 72 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: [1,1'-Biphenyl]-4,4'-diamine, 3,3',5,5'-tetramethyl-[1,1'-Biphenyl]-4,4'-diamine, 3,3',5,5'-tetramethyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Flash point data for this chemical are not available, however, it is probably combustible. (NTP, 1992) |
| Gefahrenübersicht | An irritantHarmful if swallowedMay induce methemoglobinemia if absorbed[Alfa Aesar MSDS] See Benzidine. |
| Reaktive Gruppe | Amines, Aromatic |
| Reactivity Profile | 3,3',5,5'-TETRAMETHYLBENZIDINE is sensitive to prolonged exposure to light (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (29.2%) |
| Brandbekämpfung | Fires involving this compound can be controlled using a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992) |
| 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. |
| 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. |
| Preventive Measures | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Protective Action Criteria (PAC) | 0.44 [mg/m3]4.9 [mg/m3]29 [mg/m3] |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,000(SRC), determined from an estimated log Kow of 4.11(2) and a regression-derived equation(3), indicates that 3,3',5,5'-tetramethylbenzidine is expected to have slight mobility in soil(SRC). The first pKa of 3,3',5,5'-tetramethylbenzidine is estimated as 4.2(SRC), using an estimation method based on perturbed molecular orbital theory and linear free energy (LFER) methods(4). This pKa indicates that 3,3',5,5'-tetramethylbenzidine will partially exist in the protonated form under acidic conditions and cations have greater adsorption to soil than neutral molecules(SRC). Furthermore, 3,3',5,5'-tetramethylbenzidine is an aromatic amine which may form covalent bonds with humic materials resulting in relatively immobile quinone-like complexes(5). Volatilization of the neutral species of 3,3',5,5'-tetramethylbenzidine from moist soil surfaces is not expected to be an important fate process(SRC) based upon an estimated Henry's Law constant of 7.7X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). The conjugate acid of 3,3-dimethylbenzidine will not volatilize since cations are non-volatile(SRC). 3,3',5,5'-Tetramethylbenzidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5X10-7 mm Hg(SRC), determined from a fragment constant method(7). No data on the biodegradation of 3,3',5,5'-tetramethylbenzidine in soil were found(SRC), but a similar compound (3,3'-dimethylbenzidine) was reported to be resistant to biodegradation in the Japanese MITI test(8), suggesting biodegradation in soil will most likely occur slowly(SRC). Benzidine-based compounds such as 3,3',5,5'-tetramethylbenzidine are rapidly oxidized by Fe(III) and several other cations which are frequently found in soils and clay minerals(9).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,000(SRC), determined from an estimated log Kow of 4.11(2) and a regression-derived equation(3), indicates that 3,3',5,5'-tetramethylbenzidine is expected to adsorb to suspended solids and sediment(SRC). The first pKa of 3,3',5,5'-tetramethylbenzidine is estimated as 4.2(SRC), using an estimation method based on perturbed molecular orbital theory and linear free energy (LFER) methods(4). This pKa indicates that 3,3',5,5'-tetramethylbenzidine will partially exist in the protonated form under acidic conditions and cations have greater adsorption to suspended solids and sediment than neutral molecules(SRC). Volatilization of the free base from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.7X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). The conjugate acid of 3,3',5,5'-tetramethylbenzidine will not volatilize since cations are non-volatile(SRC). According to a classification scheme(6), an estimated BCF of 290(SRC), from its estimated log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). No data on the biodegradation of 3,3',5,5'-tetramethylbenzidine in natural waters were found(SRC), but a similar compound (3,3'-dimethylbenzidine) was reported to be resistant to biodegradation in the Japanese MITI test(8), suggesting biodegradation in water will most likely occur slowly(SRC). Benzidine-based compounds such as 3,3',5,5'-tetramethylbenzidine are rapidly oxidized by Fe(III) and several other cations which are frequently found in environmental waters, complexes of fulvic acids and in clay minerals(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,3',5,5'-tetramethylbenzidine, which has an estimated vapor pressure of 5X10-7 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',5,5'-tetramethylbenzidine 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 5 hours(SRC), calculated from its rate constant of 7.6X10-11 cu cm/molecule-sec at 25 °C (SRC) determined using a structure estimation method(3). Since 3,3',5,5'-tetramethylbenzidine absorbs light greater than 290 nm(4), it may be susceptible to direct photolysis in the environment(SRC). Particulate-phase 3,3',5,5'-tetramethylbenzidine may be removed from the air by wet and dry deposition(SRC). |
| Unerwünschte Wirkungen | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Soil Adsorption/Mobility | The Koc of 3,3',5,5'-tetramethylbenzidine is estimated as 4,000(SRC), using an estimated log Kow of 4.11(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3,3',5,5'-tetramethylbenzidine is expected to have slight mobility in soil(SRC). The first pKa of 3,3',5,5'-tetramethylbenzidine is estimated as 4.2, using an estimation method based on perturbed molecular orbital theory and linear free energy (LFER) methods(4). This estimated pKa indicates that 3,3',5,5'-tetramethylbenzidine will partially exist in the protonated form under acidic conditions and cations have greater adsorption to soils than neutral molecules(SRC). Furthermore, 3,3',5,5'-tetramethylbenzidine is an aromatic amine which may form covalent bonds with humic materials resulting in relatively immobile quinone-like complexes(5). |
| Artificial Pollution Sources | 3,3',5,5'-Tetramethylbenzidine's production and use as a clinical reagent for testing blood(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | No biodegradation data for 3,3',5,5'-tetramethylbenzidine were found(SRC). Structurally similar compounds such as 3,3'-dimethylbenzidine have been shown to undergo biodegradation slowly in screening tests(1), suggesting that 3,3',5,5'-tetramethylbenzidine is also resistant to biodegradation(SRC). |
| Environmental Bioconcentration | An estimated BCF of 290 was calculated for 3,3',5,5'-tetramethylbenzidine(SRC), using an estimated log Kow of 4.11(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). |
| Volatilization from Water/Soil | The first pKa of 3,3',5,5'-tetramethylbenzidine is estimated as 4.2(SRC), using an estimation method based on perturbed molecular orbital theory and linear free energy (LFER) methods(1). This estimated pKa indicates that 3,3',5,5'-tetramethylbenzidine will partially exist in the protonated form under acidic conditions and cations will not volatilize from water or soil surfaces(SRC). The Henry's Law constant for the neutral species (free base) of 3,3',5,5'-tetramethylbenzidine is estimated as 7.7X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(2). This Henry's Law constant indicates that 3,3',5,5'-tetramethylbenzidine is expected to be essentially nonvolatile from water surfaces(3). 3,3',5,5'-Tetramethylbenzidine's Henry's Law constant(2) indicates that volatilization from moist soil surfaces is not expected(SRC). 3,3',5,5'-Tetramethylbenzidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5X10-7 mm Hg(SRC), determined from a fragment constant method(4). |
| Non-Human Toxicity Excerpts | ...HAS PRODUCED NO TUMORS SPECIFICALLY ATTRIBUTABLE TO IT WHEN INJECTED SC INTO RATS IN DOSES GREATER THAN THOSE IN WHICH BENZIDINE & O-TOLIDINE CAUSE HIGH YIELD OF NEOPLASMS.MUTAGENICITY OF URINE FROM RATS TREATED WITH ARYLAMINES (0.25 MMOL/KG IP) WAS STUDIED USING AMES ASSAY (SALMONELLA TYPHIMURIUM). NO MUTAGENICITY WAS OBSERVED IN URINE COLLECTED 24 HR AFTER ADMIN OF 3,3'-5,5'-TETRAMETHYLBENZIDINE.ANALOGS OF BENZIDINE WERE ASSAYED FOR MUTAGENIC ACTIVITY TOWARD SALMONELLA TYPHIMURIUM TA-1538 IN PRESENCE & ABSENCE OF RAT LIVER ENZYME PREPARATION. 3,3',5,5'-TETRAMETHYLBENZIDINE HAD NO MUTAGENIC ACTIVITY ALONE OR IN CONJUNCTION WITH A LIVER PREPARATION.PROLONGED SC ADMIN TO RATS GAVE NEGLIGIBLE YIELD OF TUMORS, UNLIKE RESULTS OF ADMIN OF BENZIDINE & O-TOLIDINE. THIS SENSITIVE & SPECIFIC AGENT FOR DETECTION OF BLOOD MIGHT DISPLACE USE OF LATTER SUBSTANCES.For more Non-Human Toxicity Excerpts (Complete) data for 3,3',5,5'-TETRAMETHYLBENZIDINE (6 total), please visit the HSDB record page. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 3,3',5,5'-tetramethylbenzidine with photochemically-produced hydroxyl radicals has been estimated as 7.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The first pKa of 3,3',5,5'-tetramethylbenzidine is estimated as 4.2(SRC), using an estimation method based on perturbed molecular orbital theory and linear free energy (LFER) methods(2). This pKa indicates that 3,3',5,5'-tetramethylbenzidine will partially exist in the protonated form under acidic conditions(SRC). 3,3',5,5'-Tetramethylbenzidine absorbs light greater than 290 nm(3) and may be susceptible to photolysis in the environment(SRC). Benzidine-based compounds such as 3,3',5,5'-tetramethylbenzidine are rapidly oxidized by Fe(III) and several other cations which are frequently found in environmental waters, complexes of fulvic acids and in clay minerals(3). 3,3',5,5'-Tetramethylbenzidine is not expected to undergo hydrolysis due to a lack of hydrolyzable functional groups(4). |
| Probable Routes of Human Exposure | Occupational exposure to 3,3',5,5'-tetramethylbenzidine may occur through inhalation and dermal contact with this compound at workplaces where 3,3',5,5'-tetramethylbenzidine is produced or used. (SRC) |
| Environmental Fate/Exposure Summary | 3,3',5,5'-Tetramethylbenzidine's production and use as a clinical reagent for testing blood may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 5X10-7 mm Hg at 25 °C indicates 3,3',5,5'-tetramethylbenzidine will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3,3',5,5'-tetramethylbenzidine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicalsthe half-life for this reaction in air is estimated to be 5 hours. 3,3',5,5'-Tetramethylbenzidine absorbs light greater than 290 nm, and it may be susceptible to direct photolysis in the environmenthowever, the rate of this potential reaction is unknown. Particulate-phase 3,3',5,5'-tetramethylbenzidine will be removed from the atmosphere by wet and dry deposition. If released to soil, 3,3',5,5'-tetramethylbenzidine is expected to have slight mobility based upon an estimated Koc of 4,000. The first pKa of 3,3',5,5'-tetramethylbenzidine is estimated as 4.2, which indicates that this compound will partially exist in the protonated form under acidic conditions and cations have greater adsorption to soils than neutral molecules. Furthermore, 3,3',5,5'-tetramethylbenzidine is an aromatic amine which may form covalent bonds with humic materials resulting in relatively immobile quinone-like complexes. Volatilization from moist soil surfaces is not expected to be an important fate process for 3,3',5,5'-tetramethylbenzidine because cations do not volatilize, and the estimated Henry's Law constant of the neutral species is 7.7X10-11 atm-cu m/mole. 3,3',5,5'-Tetramethylbenzidine is not expected to volatilize from dry soil surfaces based upon its estimated vapor pressure. No data regarding the biodegradation of 3,3',5,5'-tetramethylbenzidine in soil or natural water were foundhowever, a screening study on a similar compound, 3,3'-dimethylbenzidine, using sewage sludge inoculum, suggests biodegradation will occur slowly in the environment. Benzidine-based compounds such as 3,3',5,5'-tetramethylbenzidine are rapidly oxidized by Fe(III) and several other cations which are frequently found in environmental waters and soil. If released into water, 3,3',5,5'-tetramethylbenzidine is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process for either the free base or its conjugate acid based upon this compound's estimated Henry's Law constant and the fact that cations are non-volatile. An estimated BCF of 290, suggests the potential for bioconcentration in aquatic organisms is high. 3,3',5,5'-Tetramethylbenzidine is not expected to undergo hydrolysis due to a lack of hydrolyzable functional groups. Occupational exposure to 3,3',5,5'-tetramethylbenzidine may occur through inhalation and dermal contact with this compound at workplaces where 3,3',5,5'-tetramethylbenzidine is produced or used. (SRC) |
| Antidote and Emergency Treatment | Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . 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 normal saline 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 patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/ |
| F | 8-10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2796 8/PG 2 |
| Zollcode | 29215990 |
| RTECS-Nr. | DV2300000 |
| R-Sätze (R) | 36/38-36/37/38-22-41 |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 26-36-36/37-39 |
| Gefahrenklasse | 6.1Acute Tox. 4 OralAquatic Chronic 4Carc. 2 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 54827-17-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Tetramethylbenzidine(TMB) is a chromogenic substrate used in staining procedures in immunohistochemistry as well as being a visualising reagent used in enzyme-linked immunosorbent assays (ELISA). It is a white solid that forms a pale blue-green liquid in solution with ethyl acetate. TMB is degraded by sunlight and by fluorescent lights. It is a soluble chromogen substrate for horseradish peroxidase detection systems. Tetramethylbenzidine is recommended for ELISA procedures.
Herstellung & Synthese
synthetische
The synthesis of 3,3',5,5'-Tetramethylbenzidine involved using 2,6-dimethylaniline as the raw material. The process included activation, oxidative coupling, and purification, resulting in the production of pure material. The yield of 3,3,5,5-tetramethylbenzidine was 65%.