化工社化工社 化学情報印刷レポート · 研究参考用
1,2-フェニレンジアミン
1,2-フェニレンジアミン · o-フェニレンジアミン · 1,2-ベンゼンジアミン · ベンゼン-1,2-ジアミン · 1,2-ジアミノベンゼン · o-ジアミノベンゼン · C.I.オキシデーションベース16 · 2-アミノアニリン
識別子と物理属性
| CAS No. | 95-54-5 |
|---|---|
| 分子式 | C6H8N2 |
| 平均分子量 | 108.14 g/mol |
| 単同位体質量 | 108.06874826 g/mol |
| SMILES | Nc1ccccc1N |
| InChIKey | GEYOCULIXLDCMW-UHFFFAOYSA-N |
| PubChem CID | 7243 |
| ChEMBL | CHEMBL70582 |
| ChEBI | CHEBI:34043 |
| EC No. | 202-430-6 |
| DTXSID | DTXSID3025881 |
| 現地名 | 1,2-フェニレンジアミン |
化学・物理的性質
| XLogP | 0.1 |
|---|---|
| 極性表面積 | 52 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 62 |
| LogP（分配係数） | log Kow = 0.150.15 (calculated) |
| Color/Form | Brownish-yellow leaflets from waterplates from chloroformTan crystals or leaflets from waterWhite crystalline solid when pure |
| 溶解度 | less than 1 mg/mL at 68 °F (NTP, 1992)Because of ... limited solubility in cold water/o-phenylenediamine/ can be recrystalized from waterFreely soluble in alcohol, chloroform, etherSoluble in water, ethyl ether, benzene, chloroformvery soluble in ethanolIn water, 4.07X10+4 mg/L at 35 °CSolubility in water, g/100ml at 35 °C: 0.4H2O：1錠/10mL、無色透明<0.1 g/100 mL で 20 ºC |
| 引火点 | 313 °F (NFPA, 2010)156 °C (Closed cup)156 °C c.c.110°C |
| 沸点 | 493 to 496 °F at 760 mmHg (NTP, 1992)257 °C256-258 °C493-496 °F257 °C @760 [mm Hg] |
| Decomposition | When heated to decomp, it emits toxic fumes of /nitrogen oxides/. |
| 融点 | 216 to 219 °F (NTP, 1992)102.1 °C103-104 °C216-219 °F100-102 °C |
| 蒸気密度 | Relative vapor density (air = 1): 3.733.7 (vs air) |
| 蒸気圧 | 2.06X10-3 mm Hg at 25 °CVapor pressure, kPa at 20 °C: 0.00130.01 mm Hg ( 25 °C) |
| Physical Description | 1,2-phenylenediamine appears as colorless monoclinic crystals if puretechnical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.Dry PowderLiquidColorless to brownish-yellow solid that darkens on exposure to light and air[CHEMINFO]BROWN-TO-YELLOW CRYSTALS. TURNS DARK ON EXPOSURE TO LIGHT.Colorless monoclinic crystals if puretechnical grade brownish-yellow crystals or a sandy brown solid. |
| Dissociation Constants | pKa1 = less than 2pKa2 = 4.47 at 25 °C |
| Collision Cross Section | 129.1 Ų [M+H]+ |
| 密度 | 1,27 g/cm3 |
| 屈折率 | 1.6339 (estimate) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | タブレット |
| pKa（酸解離定数） | 4.46(at 25℃) |
| 色 | ホワイトからオフホワイト |
| pH | 7-8 (50g/l, H2O, 20℃) |
| 爆発限界 | 1.5%(V) |
| Merck | 14,7284 |
| BRN | 606074 |
| ヘンリー定数 | 1.4×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| 主な用途 | 底面反射防止コーティング、半導体デバイス、毛髪染料、検出抗体、ウマ抗体基質、グルコース、ストレプトマイシン、ペニシリン、スルホンアミド、ニューログロビン、西洋ワサビペルオキシダーゼ基質 |
| InChI | 1S/C6H8N2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H2 |
| InChIKey | GEYOCULIXLDCMW-UHFFFAOYSA-N |
| SMILES | Nc1ccccc1N |
| LogP（分配係数） | 0.12-0.17 at 20-25℃ and pH7-8 |
| CAS データベース | 95-54-5(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,2-Benzenediamine(95-54-5) |
| EPAの化学物質情報 | 1,2-Phenylenediamine (95-54-5) |
化学的特性
o-Phenylenediamine is a white to brownish crystalline substance that turns red upon exposure to air.
安全性と法規制
| GHS 分類 | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]H312: Harmful in contact with skin [Warning Acute toxicity, dermal]H317: May cause an allergic skin reaction [Warning Sensitization, Skin]H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332: Harmful if inhaled [Warning Acute toxicity, inhalation]H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]H351: Suspected of causing cancer [Warning Carcinogenicity]H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P203, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P330, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: 1,2-BenzenediamineHazard Traits - CarcinogenicityAuthoritative List - IARC Carcinogens - 2BProp 65Report - regardless of intended function of ingredient in the product1,2-Benzenediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenediamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 02-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2001Status: Active Update: 31-10-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1268Status: Active Update: 30-07-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/13991,2-Phenylenediamine: HSNO Approval: HSR003048 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.) |
| その他の安全情報 | IMAP assessments - 1,2-Benzenediamine: Human health tier II assessmentEvaluation - Phenylenediamines |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this chemical may include skin and eye irritation, headache, drowsiness, mental confusion and liver damage.ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. It is highly toxic by inhalation and skin absorption. (NTP, 1992) |
| 有害性の概要 | At lethal concentrations, exposed animals have seizures and paralysis without anesthesia. [ChemIDplus] Methemoglobinemia is observed in acute animal studies. In subchronic studies, rats have anemia and elevated liver enzymes. Critical Effects are irritationblood[ACGIH] |
| 反応性グループ | Amines, Aromatic |
| EC 分類 | Symbol: T, NR: 20/21-25-36-40-43-50/53-68S: (1/2)-28-36/37-45-60-61Note: C |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: III |
| Special Reports | TSCA CHIPs present a preliminary assessment of 1,2-Benzenediamine's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404. |
| TSCA 要件 | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenediamine is included on this list. Effective date: 4/29/83Sunset date: 4/29/93.All persons who manufacture (including import or by-product manufacture) or process o -pda, or intend to manufacture or process ortho-phenylenediamine after the effective date of this rule to the end of the reimbursement period shall submit letters of intent to test, submit study plans, conduct tests, and submit data, or submit exemption applications as specified in paragraphs (c)(3), (d), and (e) of this section, subpart A of this part, and parts 790 and 792 of this chapter for single-phase rulemaking. Required testing: health efffects, chemical fate and environmental effects testing. |
| Reactivity Profile | 1,2-PHENYLENEDIAMINE a weak aromatic amine base neutralizes acids in exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Darkens on exposure to air (Roger Patrick, DuPont Engineer). |
| 消火 | Fires involving this material can be controlled with a dry chemical, car bon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder. |
| 応急処置措置 | Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.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.Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention . |
| 応急処置 | 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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif 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. (NTP, 1992) |
| 安全保管 | Separated from food and feedstuffs. Well closed. |
| 消火手順 | Use water spray, powder. |
| 保管条件 | Separated from food and feedstuffs. Well closed. |
| 清掃方法 | Spillage Disposal. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do not let this chemical enter the environment. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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 keep this material in a tightly closed container under an inert atmosphere, protect it from light, and store it at refrigerated temperatures. (NTP, 1992) |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.Recommendable method: Incineration. (Peer-review conclusions of an IRPTC expert consultation (May 1985)) |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | Do not eat, drink, or smoke during work. Wash hands before eating. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| 生態毒性値 | LC50Species: Brachydanio rerio (Zebrafish)Concentration: 24 mg/L for 96 hr /Conditions of bioassay not specified/LC100Concentration: 33 mg/L for 96 hr /Conditions of bioassay not specified/Species: Pimephales promelas (Fathead minnow)Concentration: 44 mg/L for 96 hr /Conditions of bioassay not specified/Concentration: 271 mg/L for 96 hr /Conditions of bioassay not specified/For more Ecotoxicity Values (Complete) data for O-PHENYLENEDIAMINE (6 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that o-phenylenediamine is expected to have very high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of o-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), based upon its vapor pressure, 2.06X10-3 mm Hg(5), and water solubility, 4.04X10+4 mg/L(6). o-Phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). A 100% of total decomposition required greater than 64 days using a soil inoculum(7), suggesting that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that o-phenylenediamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.06X10-3 mm Hg(4), and water solubility, 4.04X10+4 mg/L(5). The pKa values of <2 and 4.47(6) indicate o-phenylenediamine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(7), an estimated BCF of 3(SRC),from its log Kow of 0.15(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). o-Phenylenediamine exhibited 33% removal after 5 days incubation using acclimated activated sludge inoculum(10), suggesting that biodegradation may be an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-phenylenediamine, which has a vapor pressure of 2.06X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase o-phenylenediamine 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 0.7 hours(SRC), calculated from its rate constant of 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). o-Phenylenediamine absorbs light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| 有害作用 | 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.Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effectIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.ACGIH Carcinogen - Confirmed Animal. |
| 暴露経路 | The substance can be absorbed into the body by inhalation and by ingestion. |
| 生態毒性抜粋 | /AQUATIC SPECIES/ The static acute toxicities and degradative rates of the unsubstituted phenylenediamines (pdas) varied significantly among the ortho, para and meta isomers. With fathead minnows, the nominal 96 hr LC50s were 0.06, 44 and 1,600 mg/L for p-pda, o-pda and m-pda, respectively. In daphnid tests, the nominal 48 hr EC50s were 0.28, 0.87 and 5.9 mg/L for p-pda, o-pda and m-pda, respectively. The nominal 96 hr EC50s in algae were 0.28, 0.16, and 2.4 mg/L for p-pda, o-pda and m-pda, respectively. With oxygenation, the times to reach 1/2 initial concentrations were 4 to 9 hr for p-pda, 650 to 1,100 hr for o-pda and 3,200 to 8,100 hr for m-pda. Results suggest that acute toxicities of pdas are related to their chemical reactivities (degradative rates) and that pdas may degrade rapidly under environmental conditions./OTHER TERRESTRIAL SPECIES/ ...The toxicity of 10 benzamines was tested by the well diffusion assay technique against 18 common bacterial species including the nitrogen-fixing bacterium Azotobacter vinelandii. ... o-Phenylenediamine was inhibitory to Escherichia coli, Klebsiella pnemoniae, Salmonella enteritidis, and Shigella sonnei. ... Because many of these organisms are common soil and aquatic bacteria, the accumulation of these benzamine compounds in the environment may have an adverse impact on soil biochemical activities./PLANTS/ Three isomers of the promutagen phenylenediamine at mM concentrations were plant-activated and induced mutation in stamen hairs of Tradescantia clone 4430. The rank order of the mutagenicity of the isomers was: o-phenylenediamine > m-phenylenediamine > p-phenylenediamine with corresponding mutagenic potencies of 5.60, 1.43, and 0.46 mutant stamen hair cells/mumole, respectively. Diethyldithiocarbamate (DEDTC) and ammonium meta-vanadate (vanadate) repressed the mutagenic activity of o-phenylenediamine (o-PDA) in intact plants. Based on inhibition kinetics and reaction rates, the mechanism of DEDTC antimutagenicity was attributed to the inhibition of peroxidases that are required in the plant activation of o-PDA to mutagenic product(s). Spectrophotometric measurements of equimolar concentrations of o-PDA and vanadate demonstrated that the antimutagenic property of vanadate was mainly due to its reactivity with o-PDA. |
| Signs and Symptoms | Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.Redness.Redness. Pain.See Inhalation. |
| 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 November 6, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=95-54-5] |
| ICSC Environmental Data | The substance is very toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of o-phenylenediamine can be estimated to be 34(SRC). According to a classification scheme(2), this estimated Koc value suggests that o-phenylenediamine is expected to have very high mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). |
| TSCA Test Submissions | 1,2-Benzenediamine (CAS # 95-54-5) was evaluated for eye irritation in 3 albino rabbits administered undiluted ocular instillations of 100 mg. The treated eyes remained unrinsed during post-instillation observation. Ocular irritation was maximal in all 3 rabbits 1 hour after treatment. A mean irritation score was 31.7/110. One rabbit remained unimproved at 72nd hour observation, developing corneal ulceration and vascularization by the 7th day, while Day 7 found complete resolution of all irritative signs in the other 2 treated rabbits. By 14th day observation period, one rabbit continued to show corneal vascularization and ulceration with slight conjunctival redness comprising an individual irritation score of 12/110 and a mean score (3 rabbits) of 4.0/110. Study investigators assigned a descriptive rating of "moderately irritating" to 1,2-benzenediamine.o-Phenylenediamine (CAS # 95-54-5) was evaluated for oral neurotoxicity in Crl:CDBR rats (12/sex/group) administered single gavage doses of 0, 225, 450, and 900 mg/kg (10 mL/kg in methyl cellulose). Bodyweight, feed consumption, clinical signs, functional observational battery performance, fore- and hindlimb grip strength, foot splay and motor activity were assessed prior to treatment (baseline values), and at 1 hour, 24 hours, and 4 days post-treatment. Toxicity was demonstrated at all dose levels. High-dose rats, 2 males and 4 females were found dead prior to scheduled sacrifice and significant weight loss within one day of dosing was common to all treatment groups, persisting throughout Day 4. Significant reductions in feed consumption were pronounced initially, but transient in all but the high-dose group. Clinical signs were most severe 2-4 days after treatment and included initial discolored urine, abnormal respiration with gasping, congestion, and sneezing (450, 900 mg/kg), dose-related malaise, postural changes, palpebral closure, and decreased arousal. The functional observational battery, fore-, and hindlimb grip strength and foot splay assessments were not indicative of a neurotoxicity at any treatment level. Motor activity was significantly depressed following treatment in all treatment groups relative to control. Study investigators attributed these findings to a general condition of dose-related malaise and reported no evidence of specific toxic effects on the central nervous system.Acute dermal toxicity was evaluated in single New Zealand female rabbits receiving one occluded application of o-phenylenediamine to abraded skin at dose levels of 300, 1000, or 3000 mg/kg body weight for 24 hours. Mortality was not observed in any animal at any dose level, and the LD50 was reported to be greater than 3000 mg/kg. Clinical signs of toxicity were not observed, and the test article was not irritating to rabbit skin. Gross necropsy did not reveal any evidence of pathological effects.Acute inhalation toxicity was evaluated in 10 BR rats (5 male and 5 female) exposed to o-phenylene diamine vapor at a nominal concentration of 1340.0 mg/cu m for 4 hours. The atmosphere was generated by passing a stream of air through the test material in a gas wash bottle. Mortality was not observed in any animal during exposure or a 14 day observation period, and the LC50 was reported to be greater than 1340 mg/cu m. Clinical indications of toxicity were not observed, and necropsy of animals at 14 days did not reveal gross pathologic alterations.For more TSCA Test Submissions (Complete) data for O-PHENYLENEDIAMINE (8 total), please visit the HSDB record page. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Produces severe local reactions and systemic effects from percutaneous absorption and from ingestion. Local actions include severe dermatitis and urticariain the eye, chemosis, lacrimation, exophthalmos, ophthalmia, and even permanent blindness. Systemic actions include asthma, gastritis (regardless of portal of entry), rise in blood pressure, transudation into serous cavities, vertigo, tremors, convulsions and coma. ... The ortho isomer (diolene) is less toxic than the para (orsin). Neither is believed to be capable of inducing significant methemoglobinemia./GENOTOXICITY/ Chromosomal aberration tests that were performed ... in peripheral human lymphocytes were ... positive with metabolic activation. |
| Artificial Pollution Sources | o-Phenylenediamine occurs as degradation product of thiophanate methyl & benomyl (benzimidazole fungicides).o-Phenylenediamine's production and use as a chemical intermediate in the manufacture of dyes, photographic developing agent, organic synthesis, and as a laboratory reagent(1) may result in its release to the environment through various waste streams(SRC). |
| F | 8-10-23 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | SS7875000 |
| 輸送番号（UN） | UN 1673 (PHENYLENEDIAMINES (o-, m-, p-)) |
| 毒性 | LD50 in rats (mg/kg): 1070 orally516 i.p., C. Burnett et al., J. Toxicol. Environ. Health 2, 657 (1977) |
| PRTR法 | 第一種指定化学物質 |
| 税関コード | 29215119 |
| 危険文句（R） | 20/21-25-36-40-43-50/53-68 |
| 化審法 | (3)-185 優先評価化学物質 |
| 安衛法 | 変異原性物質 |
| 危険表示 | T,N |
| 安全措置（S） | 28-36/37-45-60-61-1/2 |
| 危険等級 | 6.1Acute Tox. 3 OralAcute Tox. 4 DermalAcute Tox. 4 InhalationAquatic Acute 1Aquatic Chronic 1Carc. 2Eye Irrit. 2Muta. 2Skin Sens. 1 |
| 包装等級 | III |
| 毒劇物取締法 | 劇物 |
| 自然発火温度 | 540 °C |
| 環境リスク評価 | o-フェニレンジアミン(95-54-5) |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 有害物質データ | 95-54-5(Hazardous Substances Data) |
用途
解説
C6H4(NH2)2．ベンゼン環にアミノ基2個をもつ芳香族ジアミン．o-フェニレンジアミン，m-フェニレンジアミン，p-フェニレンジアミンの3種の異性体がある．いずれも有機合成の原料として，たとえば，染料合成の中間物としての用途が広い．
用途
染料、酸化防止剤、写真用薬剤、ポリアミド線維、殺虫剤、薬品。
用途
EIA法において、パーオキシダーゼ標識抗体、過酸化水素とともに用いる。
使用
o-Phenylenediamine is an amino substituted benzene used in the manufacture of dyes. Potential use in sensitive immunosensor for cancer biomarker.Environmental toxin on US EPA Toxic Release Inventory list (TRI) list.
一般的な説明
Colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.
製法・合成法
純化方法
Crystallise the diamine from aqueous 1% sodium hydrosulfite (charcoal), wash it with ice-water and dry it in a vacuum desiccator, or sublime it in vacuo. It has been purified by recrystallisation from toluene and zone refined [Anson et al. J Am Chem Soc 108 6593 1986]. Purification by refluxing a CH2Cl2 solution containing charcoal is also carried out followed by evaporation and recrystallisation [Koola & Kochi J Org Chem 52 4545 1987], protect from light. The acetate has m 186o. [Beilstein 13 IV 38.]