化工社化工社 化学情報印刷レポート · 研究参考用
4-クロロ-1,2-フェニレンジアミン
4-クロロ-1,2-フェニレンジアミン · ウルソールオリーブ6G · 4-クロロ-o-フェニレンジアミン · 1-クロロ-3,4-ジアミノベンゼン · 4-クロロベンゼン-1,2-ジアミン · 4-クロロ-1,2-ベンゼンジアミン · 2-アミノ-4-クロロアニリン · 4-クロロ-1,2-ジアミノベンゼン
識別子と物理属性
| CAS No. | 95-83-0 |
|---|---|
| 分子式 | C6H7ClN2 |
| 平均分子量 | 142.58 g/mol |
| 単同位体質量 | 142.0297759 g/mol |
| SMILES | Nc1ccc(Cl)cc1N |
| InChIKey | BXIXXXYDDJVHDL-UHFFFAOYSA-N |
| PubChem CID | 7263 |
| ChEMBL | CHEMBL552741 |
| ChEBI | CHEBI:82301 |
| EC No. | 202-456-8 |
| DTXSID | DTXSID5020283 |
| 現地名 | 4-クロロ-1,2-フェニレンジアミン |
化学・物理的性質
| XLogP | 1.3 |
|---|---|
| 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 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 97.1 |
| 物質分類 | Nitrogen Compounds -> Amines, AromaticCarcinogens |
| LogP（分配係数） | log Kow = 1.28 |
| Color/Form | Crystals |
| 溶解度 | less than 1 mg/mL at 66 °F (NTP, 1992)Soluble in benzene, very soluble in ethanol, ether.Slightly soluble in waterクロロホルム（微量）、メタノール（微量）16g/L（20℃） |
| 融点 | 153 to 158 °F (NTP, 1992)76 °C70-73 °C(lit.) |
| 蒸気圧 | 0.00206 [mmHg] |
| Physical Description | 4-chloro-o-phenylenediamine appears as brown crystalline solid or powder. (NTP, 1992)Brown solidMay be sensitive to prolonged exposure to air and light[CAMEO] Deep brown powder[MSDSonline] |
| 沸点 | 232.49°C (rough estimate) |
| 密度 | 1.2124 (rough estimate) |
| 屈折率 | 1.4877 (estimate) |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Room temperature |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 3.52±0.10(Predicted) |
| 色 | ホワイトからオフホワイト |
| BRN | 508472 |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| InChI | 1S/C6H7ClN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2 |
| InChIKey | BXIXXXYDDJVHDL-UHFFFAOYSA-N |
| SMILES | Nc1ccc(Cl)cc1N |
| CAS データベース | 95-83-0(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,2-Benzenediamine, 4-chloro-(95-83-0) |
| EPAの化学物質情報 | 4-Chloro-1,2-phenylenediamine (95-83-0) |
化学的特性
4-Chloro-o-phenylenediamine is a brown crystalline powder or leaflets from water; freezing/melting point 67-73°C; also reported in lit. @ 76°C. Slightly soluble in water. soluble in benzene, very soluble in ethanol, ether.
安全性と法規制
| GHS 分類 | WarningH302 (10%): 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 50 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity] |
|---|---|
| 規制情報 | Chemical: 1,2-Benzenediamine, 4-chloro-Hazard Traits - CarcinogenicityThe 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 - Chemicals with limited data availability that may be used in hair dyes overseas: Human health tier II assessment |
| 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) |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include irritation. |
| 有害性の概要 | Harmful by inhalation, ingestion, and skin absorption[CAMEO] An irritantMay induce methemoglobinemia[MSDSonline] |
| 反応性グループ | Aryl Halides |
| Special Reports | National Toxicology Program. Eleventh Report on Carcinogens (2005). 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. 4-Chloro-o-phenylenediamine (95-83-0) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s0414cop.pdf]DHEW/NCIBioassay of 4-Chloro-o-phenylenediamine for Possible Carcinogenicity (1978) Technical Rpt Series No. 63 DHEW Pub No. (NIH) 78-1313 |
| TSCA 要件 | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.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. 4-chloro-1,2-benzenediamine is included on this list. |
| Reactivity Profile | 4-CHLORO-O-PHENYLENEDIAMINE is incompatible with strong oxidizers. It reacts with alpha-ketoacids to form quinoxalones. (NTP, 1992) |
| Air and Water Reactions | This chemical may be sensitive to prolonged exposure to air and light. Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (10%)Germ cell mutagenicity - Category 2Skin corrosion/irritation - Category 2Carcinogens |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| 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. |
| 保管条件 | 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/ |
| 清掃方法 | 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/ |
| 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. |
| 処分方法 | 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.PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/For more Disposal Methods (Complete) data for 4-CHLORO-1,2-BENZENEDIAMINE (6 total), please visit the HSDB record page. |
| 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 4-CHLORO-1,2-BENZENEDIAMINE (9 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/ |
| 有害作用 | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| 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. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=95-83-0] |
| 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/ |
| Carcinogen Classification | 4-Chloro-ortho-phenylenediamineGroup 2B: Possibly carcinogenic to humansVolume 27: (1982) Some Aromatic Amines, Anthraquinones and Nitroso Compounds, and Inorganic Fluorides Used in Drinking-water and Dental Preparations19874-Chloro-o-phenylenediamine |
| Non-Human Toxicity Excerpts | 4-CHLORO-O-PHENYLENEDIAMINE ADMIN TO RATS @ 1.0 & 0.5% TIME-WEIGHTED AVG DIETARY CONCN FOR 78 WK. INCR INCIDENCE OF NEOPLASMS OF BLADDER OCCURRED. COMPD IS BLADDER CARCINOGEN IN MALE & FEMALE FISCHER 344 RATS.4-CHLORO-O-PHENYLENDIAMINE ADMIN TO MICE @ 1.4 & 0.7% TIME-WEIGHTED AVG DIETARY CONCN FOR 78 WK. INCR INCIDENCE OF HEPATOCELLULAR CARCINOMAS OCCURRED. COMPD IS HEPATOCARCINOGEN IN MALE & FEMALE B6C3F1 MICE.IN BOTH MALE & FEMALE FISCHER RATS, FEEDING 4-CHLORO-O-PHENYLENEDIAMINE @ 0.5 OR 1% IN DIET LED TO SIGNIFICANT INCREASE IN HYPERPLASIA, PAPILLOMA & CARCINOMA OF URINARY BLADDER.When administered in the diet, technical-grade 4-chloro-o-phenylenediamine induced carcinomas of the urinary bladder in rats of both sexes and hepatocellular carcinomas of the liver in mice of both sexes.For more Non-Human Toxicity Excerpts (Complete) data for 4-CHLORO-1,2-BENZENEDIAMINE (7 total), please visit the HSDB record page. |
| Evidence for Carcinogenicity | No data are available in humans. Sufficient evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 2B: The agent is possibly carcinogenic to humans.4-Chloro-o-phenylenediamine: reasonably anticipated to be a human carcinogen. |
| Probable Routes of Human Exposure | The primary routes of potential human exposure to 4-chloro-o-phenylenediamine are ingestion, inhalation, and dermal contact during its production. Exposure could occur if accidental releases of the cmpd into the work environ took place. Potential exposure is limited to the single production site.Consumer exposure could potentially occur from residues in hair dyes or in products made from 5-chlorobenzotriazole. |
| RAIS Toxicity Values | 4.6e-06CALEPA0.016 |
| F | 8 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | SS8850000 |
| 輸送番号（UN） | 2811 |
| 税関コード | 29215900 |
| 危険文句（R） | 36/37/38-40 |
| 化審法 | (3)-267 |
| 安衛法 | 変異原性物質 |
| 危険表示 | Xn |
| hazard_note | Irritant |
| 安全措置（S） | 26-36/37 |
| 危険等級 | Carc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 95-83-0(Hazardous Substances Data) |
用途
用途
有機合成原料。
用途
染料製造、ヘアカラーの酸化剤
使用
4-Chloro-o-phenylenediamine can be used as an oxidation base for dye preparation, as a chemical intermediate to produce 5-chlorobenzotriazole, as a curing agent for epoxy resins, as a reagent in gas chromatography, and to synthesize experimental pharmaceuticals. It has been used as a chemical intermediate in dye production and was patented as a hair-dye component, but there is no evidence that it is currently used in the United States for these purposes (IARC 1982, HSDB 2009).
一般的な説明
4-chloro-o-phenylenediamine appears as brown crystalline solid or powder. (NTP, 1992)
製法・合成法
調製方法
Commercial production of 4-chloro-o-PDA in the United States was first reported in 1941. About 0.45–4.5 thousand kg was produced by a U.S. company in 1977. It was also produced by one company in the Federal Republic of Germany. This compound has been patented as a hair dye component, fur dyes, inks, and hair coloring formulations, and is believed to be used to produce 5-chlorobenzotriazole, an isomer of which is a photographic chemical. The primary routes of potential human exposure to 4- chloro-o-PDA are inhalation and dermal contact during its production. Consumer exposure may occur from use of hair dyes or products made from 5-chlorobenzotriazole.
純化方法
Recrystallise the diamine from pet. ether. [Beilstein 13 IV 68.]