化工社化工社 化学情報印刷レポート · 研究参考用
2-ニトロ-1,4-フェニレンジアミン
2-ニトロ-1,4-フェニレンジアミン · 2-ニトロ-1,4-ベンゼンジアミン · 2-ニトロ-1,4-ジアミノベンゼン · ズラフルブラウン2R · 1,4-ジアミノ-2-ニトロベンゼン · フォウラミン2R · 2-ニトロ-p-フェニレンジアミン · 2,5-ジアミノ-1-ニトロベンゼン
識別子と物理属性
| CAS No. | 183870-67-9 |
|---|---|
| 分子式 | C6H7N3O2 |
| 平均分子量 | 153.14 g/mol |
| 単同位体質量 | 153.05382646 g/mol |
| SMILES | Nc1ccc(N)c([N+](=O)[O-])c1 |
| InChIKey | HVHNMNGARPCGGD-UHFFFAOYSA-N |
| PubChem CID | 4338370 |
| ChEMBL | CHEMBL353971 |
| ChEBI | CHEBI:76394 |
| EC No. | 226-164-5 |
| DTXSID | DTXSID4020957 |
| 現地名 | 2-ニトロ-1,4-フェニレンジアミン |
化学・物理的性質
| XLogP | 0.5 |
|---|---|
| 極性表面積 | 97.9 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 0 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 156 |
| 物質分類 | Nitrogen Compounds -> Nitroanilines |
| 化粧品 | Cosmetic ingredients (2-Nitro-p-Phenylenediamine) -> CIR (Cosmetic Ingredient Review)Hair dyeing |
| LogP（分配係数） | log Kow = 0.533.7 |
| Color/Form | Almost black needles with dark-green luster |
| 溶解度 | less than 1 mg/mL at 72 °F (NTP, 1992)Slightly sol in water (0.18% w/w)ethanol, polar organic compounds and benzenesoluble in acetone and diethyl etherSolubility in water, g/100ml: 0.180.2g/リットル<0.1 g/100 mL で 22 ºC |
| 融点 | 279 °F (NTP, 1992)140 °C137 °C135-138 °C (lit.) |
| 蒸気圧 | 0.000056 [mmHg] |
| Physical Description | Almost black needles with dark-green luster or black powder. (NTP, 1992)Almost black needles with dark-green luster or black powder[CAMEO]RED-TO-BROWN CRYSTALLINE POWDER. |
| 沸点 | 276.04°C (rough estimate) |
| 密度 | 1.3682 (rough estimate) |
| 屈折率 | 1.6500 (estimate) |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Room temperature |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 4.36±0.10(Predicted) |
| 色 | ブラウンからブラック |
| pH | 7 (H2O)(aqueous suspension) |
| BRN | 2210195 |
| ヘンリー定数 | 1.7×105 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| 化粧品成分の機能 | ヘアカラーリング |
| InChI | 1S/C6H7N3O2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H,7-8H2 |
| InChIKey | HVHNMNGARPCGGD-UHFFFAOYSA-N |
| SMILES | Nc1ccc(N)c(c1)[N+]([O-])=O |
| LogP（分配係数） | 0.53 |
| CAS データベース | 5307-14-2(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,4-Benzenediamine, 2-nitro-(5307-14-2) |
| EPAの化学物質情報 | 2-Nitro-p-phenylenediamine (5307-14-2) |
化学的特性
Dark red crystal Powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 1.3% (1 of 75) of reports.WarningH315 (17.3%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 75 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: 1,4-Benzenediamine, 2-nitro-Status: Cease Manufacture Update: 30-09-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/174052-Nitro-1,4-phenylenediamine: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | PEC / SN / Other assessments - Common skin sensitisersâhazard classification: Health |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | 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. |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include irritation. |
| 有害性の概要 | Allergic contact dermatitis reported in hairdressers[Kanerva, p. 1819] May cause skin sensitization[ICSC] Danger of skin sensitization[MAK] |
| 反応性グループ | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| Special Reports | 2-Nitro-p-phenylenediamine. a component of both semipermanent and permanent hair dye formulations, was selected for bioassay by the National Cancer Institute because of the increased incidence of bladder cancer among dye manufacturing industry workers. Aromatic amines are one of several classes of organic chemicals thought to contribute to the increased cancer risk in this industry. The widespread exposure to 2-nitro-p-phenylenediamine among the general population, and the possibility of an increased cancer risk among hairdressers were additional factors in the selection of this compound for testing. A bioassay for the possible carcinogenicity of 2-nitro-p-phenylenediamine was conducted using Fischer 344 rats and B6C3F1 mice. ... Under the conditions of this bioassay, dietary administration of 2-nitro-p-phenylenediamine was carcinogenic to female B6C3F1 mice, causing an increased incidence of hepatocellular neoplasms, primarily hepatocellular adenomas. There was no convincing evidence for the carcinogenicity of the compound in Fischer 344 rats or in male B6C3F1 mice.[DHEW/NCIBioassay of 2-Nitro-p-phenylenediamine for Possible Carcinogenicity (1979) Technical Rpt Series No. 169 DHEW Pub No. (NIH) 79-1725]A safety assessment of 2-nitro-p-phenylenediamine and 4-nitro-o-phenylenediamine was published in 1985 with the conclusion "for those persons not sensitized, the Expert Panel Concludes that 2-nitro-p-phenylenediamine and 4-nitro-o-phenylenediamine are safe as hair dye ingredients at the current concentration of use" ... Studies available since that safety assessment was completed, along with updated information regarding uses and use concentrations, were considered by the CIR Expert Panel. The Panel determined to not reopen this safety assessment.[Cosmetic Ingredient Review2-Nitro-p-Phenylenediamine and 4-Nitro-o-Phenylenediamine. JACT 4(3): 161-202, 1985Re-Review: International Journal of Toxicology. 25(S2), 2006] |
| 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. 1,4-Benzenediamine, 2-nitro- is included on this list. Effective date 4/29/83Sunset date 4/29/93. |
| Reactivity Profile | 2-NITRO-P-PHENYLENEDIAMINE is incompatible with strong oxidizing agents. (NTP, 1992) |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes including nitrogen oxides. Reacts with strong oxidants. |
| Air and Water Reactions | This chemical may be sensitive to prolonged exposure to light and air. Insoluble in water. |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)Use water spray, powder. |
| 応急処置措置 | Fresh air, rest.Remove contaminated clothes. Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. |
| 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. |
| 安全保管 | Separated from strong oxidants. |
| 非火災時の漏出対応 | 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. |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C. |
| Skin Prevention | Protective gloves. Protective clothing. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 46(SRC), determined from a log Kow of 0.53(2) and a regression-derived equation(3), indicates that 2-nitro-p-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(4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 2-nitro-p-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2-Nitro-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.6X10-5 mm Hg(SRC), determined from a fragment constant method(6). Information is not available regarding the biodegradation potential of 2-nitro-p-phenylenediaminehowever, 80% percent of p-phenylenediamine was removed over 120 hours based on chemical oxygen demand measurements and using an activated sludge inoculum(7).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 46(SRC), determined from a log Kow of 0.53(2) and a regression-derived equation(3), indicates that 2-nitro-p-phenylenediamine is not expected to adsorb to suspended solids and sediment(SRC). 2-Nitro-p-phenylenediamine may bind strongly to organic matter as aromatic amines are highly reactive with an affinity for organic materials(4). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.8X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2-Nitro-p-phenylenediamine absorbs at a wavelength of 441 nm(8) and therefore may be susceptible to direct photolysis by sunlight(SRC). Information is not available regarding the biodegradation potential of 2-nitro-p-phenylenediaminehowever, 80% percent of p-phenylenediamine was removed over 120 hours based on chemical oxygen demand measurements and using an activated sludge inoculum(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-nitro-p-phenylenediamine, which has an estimated vapor pressure of 5.6X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-nitro-p-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 17 hours(SRC), calculated from its rate constant of 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-nitro-p-phenylenediamine may be removed from the air by wet or dry deposition(SRC). 2-Nitro-p-phenylenediamine absorbs at wavelengths of 441 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). |
| 有害作用 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| 暴露経路 | The substance can be absorbed into the body through the skin. |
| 毒性の概要 | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org |
| 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=5307-14-2] |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Medical Surveillance | Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases. |
| Soil Adsorption/Mobility | The Koc of 2-nitro-p-phenylenediamine is estimated as 46(SRC), using a log Kow of 0.53(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-nitro-p-phenylenediamine is expected to have very high mobility in soil. However, anilines (aromatic amines) are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4), suggesting that mobility may be much lower in some soils(SRC). |
| Natural Pollution Sources | ...is not known to occur as natural product. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Thirty-nine hairdressers were patch tested for 24 hours with 2-nitro-p-phenylenediamine (2NPPD). Thirty-two of the hairdressers had no history of allergic contact dermatitis from p-phenylenediamine, and none of these 32 had a positive reaction to 2NPPD. One of seven hairdressers who had experienced strongly positive reactions to p-phenylenediamine was positive for 2NPPD. The researchers suggested that this may have been a cross reaction./CASE REPORTS/ A case has been described in the literature in which a dental hygienist developed dermatitis on the skin of her left forearm where it came into frequent contact with the hair of patients. A patch test with p-phenylenediamine mix was negative at 48 and 96 hours, and, with 2% 2-nitro-p-phenylenediamine, was strongly positive at 48 hours./GENOTOXICITY/ At 50-100 ug/mL, 2-nitro-p-phenylenediamine induced chromosome & chromatid gaps & breaks in human peripheral blood lymphocytes./GENOTOXICITY/ 2-Nitro-p-phenylenediamie... was active in inducing unscheduled DNA synthesis in HELA human cervical cancer cells.For more Human Toxicity Excerpts (Complete) data for 2-NITRO-P-PHENYLENEDIAMINE (6 total), please visit the HSDB record page. |
| Artificial Pollution Sources | 2-Nitro-p-phenylenediamine's production and subsequent use in the production of dyes for semi-permanant and permanant hair coloring and dyeing of fur(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Information is not available regarding the biodegradation potential of 2-nitro-p-phenylenediaminehowever, 80% percent of p-phenylenediamine was removed over 120 hours based on chemical oxygen demand measurements and using an activated sludge inoculum(1). |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | ST3000000 |
| 輸送番号（UN） | 3143 |
| 税関コード | 29215119 |
| 危険文句（R） | 43-68 |
| 化審法 | (3)-402 |
| 消防法 | 危-5-II |
| 危険表示 | Xi,Xn |
| 安全措置（S） | 36/37-45 |
| 危険等級 | Skin Sens. 1 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 5307-14-2(Hazardous Substances Data) |
用途
用途
有機合成原料。
説明
o-Nitro-paraphenylenediamine (ONPD) is a hair dye and a sensitizer in hairdressers.
使用
This compound is used in hair and fur dyes.
一般的な説明
Almost black needles with dark-green luster or black powder.