化工社化工社 化学情報印刷レポート · 研究参考用
2,5-ジクロロアニリン
2,5-ジクロロアニリン · 2，5ジクロロアニリン · 2・5-ジクロロアニリン · 2,5‐ジクロロアニリン · Fast scarlet GG salt · 2,5-Dichlorobenzenamine · 2,5-dca · CI 37010
識別子と物理属性
| CAS No. | 95-82-9 |
|---|---|
| 分子式 | C6H5Cl2N |
| 平均分子量 | 162.01 g/mol |
| 単同位体質量 | 160.97990452 g/mol |
| SMILES | Nc1cc(Cl)ccc1Cl |
| InChIKey | AVYGCQXNNJPXSS-UHFFFAOYSA-N |
| PubChem CID | 7262 |
| ChEMBL | CHEMBL1406206 |
| ChEBI | CHEBI:34245 |
| EC No. | 202-455-2 |
| DTXSID | DTXSID6024967 |
| 現地名 | 2,5-ジクロロアニリン |
化学・物理的性質
| XLogP | 2.9 |
|---|---|
| 極性表面積 | 26 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 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, Aromatic |
| SpringerMaterials Properties | Crystal structure |
| 農薬 | Pesticide degradation product |
| LogP（分配係数） | log Kow= 2.922.75 |
| 密度 | 1.54 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.01 |
| Color/Form | Light brown or amber-colored crystalline massNEEDLES FROM PETROLEUM ETHER |
| 溶解度 | less than 1 mg/mL at 72.5 °F (NTP, 1992)Sol in dilute hydrochloric acidSlightly soluble in watersoluble in ethanol, ethyl ether, banzeneSolubility in water: none希塩酸に溶ける。約。 0.56g/L（20℃） |
| 引火点 | 235 °F (NTP, 1992)139 °C>230 °F |
| 沸点 | 484 °F at 760 mmHg (NTP, 1992)251 °C251 °C (lit.) |
| Decomposition | When heated to decomposition it emits highly toxic fumes of /hydrogen chloride/ and nitrogen oxides.380 °C. Decomposes on burning. This produces toxic fumes including nitrogen oxides and hydrogen chloride (see ICSC 0163). |
| 融点 | 120 to 124 °F (NTP, 1992)50 °C47-50 °C (lit.) |
| 蒸気密度 | Relative vapor density (air = 1): 5.6 |
| 蒸気圧 | 1Pa at 25℃ |
| 屈折率 | 1.6000 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 1.60±0.10(Predicted) |
| 外観・状態 | powder to crystal |
| 色 | White to Light yellow to Dark green |
| pH | 6.5 (0.66g/l, H2O) |
| BRN | 1447438 |
| ヘンリー定数 | 6.2×100 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。酸、酸塩化物、酸無水物、酸化剤とは混和しません。 |
| InChI | 1S/C6H5Cl2N/c7-4-1-2-5(8)6(9)3-4/h1-3H,9H2 |
| InChIKey | AVYGCQXNNJPXSS-UHFFFAOYSA-N |
| SMILES | Nc1cc(Cl)ccc1Cl |
| LogP（分配係数） | 2.92 at 20℃ |
| CAS データベース | 95-82-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzenamine, 2,5-dichloro-(95-82-9) |
| EPAの化学物質情報 | 2,5-Dichloroaniline (95-82-9) |
化学的特性
light brown solid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 0.5% (1 of 201) of reports.DangerH301+H311+H331 (19.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 201 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Warning |
|---|---|
| 規制情報 | Chemical: Benzenamine, 2,5-dichloro-Status: Active Update: 10-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/61252,5-Dichloroaniline: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Dichloroanilines: Human health tier II assessment |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Heating will cause rise in pressure with risk of bursting. |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, and mucous membranes. |
| 有害性の概要 | Causes flaccid paralysis, cyanosis, and convulsions in lethal-dose studies of guinea pigs and rabbits[RTECS] Emergency treatment: Methemoglobinemia[HSDB] A severe eye irritantCan induce methemoglobinemiaMay cause skin sensitization[ICSC] A skin, eye, and mucous membrane irritant[CAMEO] |
| 反応性グループ | Aryl Halides |
| EC 分類 | Symbol: T, NR: 23/24/25-33-50/53S: (1/2)-28-36/37-45-60-61Note: C |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: II |
| 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. 2,5-Dichlorobenzeneamine is included on this list. |
| Reactivity Profile | 2,5-DICHLOROANILINE is incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents. (NTP, 1992) |
| 大気基準 | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 2,5-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart. |
| 消火 | Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water. |
| 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. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of 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. |
| 安全保管 | Separated from strong oxidants and food and feedstuffs. |
| 消火手順 | If material on fire or involved in fire: Use dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. use water in flooding quantities as fog. /Dichloroaniline/Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Dichloroaniline/ |
| 保管条件 | STORE IN A COOL, DRY, WELL-VENTILATED LOCATION. SEPARATE FROM ACIDS, OXIDIZING MATERIALS, & COMBUSTIBLES. /DICHLOROANILINES/ |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol 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 alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate 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. |
| 漏出処分 | Personal protection: chemical protection suit including self-contained breathing apparatus. Remove all ignition sources. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | ... ANILINE SHOULD BE REACTED IN CLOSED VESSELS AS FAR AS POSSIBLE. IN FACTORIES VENTILATION SHOULD BE SUFFICIENT TO KEEP ATMOSPHERIC ANILINE CONTENT WELL BELOW PERMITTED LEVEL. /ANILINE/Eating and smoking should not be allowed in areas where liquid aniline is handled, processed, or stored. /Aniline/Clothing which becomes soaked with aniline should be promptly removed. /Aniline/In the case of /skin/ contact it should be washed for a long time with soap & tepid water. When eyes are /exposed to aniline/ copious irrigation with water is immediately necessary. ... /Aniline/For more Preventive Measures (Complete) data for 2,5-DICHLOROANILINE (8 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety goggles or face shield. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 355(2) indicates that 2,5-dichloroaniline is expected to have moderate mobility in soil(SRC). However, when released to soil containing humic material, 2,5-dichloroaniline may undergo a covalent chemical bonding resulting in its chemical alteration to a latent form resulting in strong adsorption(3). 2,5-Dichloroaniline demonstrated almost a linear rate of decomposition in Guelph loam over a 12 week period, with a half-life of 8 weeks(4). Volatilization of 2,5-dichloroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2,5-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-2 mm Hg(SRC), determined from a fragment constant method(6).AQUATIC FATE: Based on a classification scheme(1), a Koc value of 355(2) indicates that 2,5-dichloroaniline is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 30 and 219 days, respectively(SRC), using an estimation method(3). However, this model underestimates the volatilization half-life of 2,5-dichloroaniline since it does not take into account the effects of adsorption. The Koc of 355(2) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 662 days in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 317 days in a model pond 2 m deep(5). According to a classification scheme(6), an estimated BCF of 35(3,SRC), from a log Kow value of 2.92(2), suggests the potential for bioconcentration in aquatic organisms is moderate.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semi-volatile organic compounds in the atmosphere(1), 2,5-dichloroaniline, which has an estimated vapor pressure of 1.5X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,5-dichloroaniline 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) from its estimated rate constant of 2.2X10-12(3). |
| 有害作用 | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| 暴露経路 | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. |
| Signs and Symptoms | Blue lips, fingernails and skin. Dizziness. Headache. Nausea. Shortness of breath. Confusion. Convulsions. Unconsciousness.MAY BE ABSORBED! Further see Inhalation.Redness. Pain. Blurred vision.Abdominal pain. Further see Inhalation. |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. |
| Soil Adsorption/Mobility | The Koc for 2,5-dichloroaniline is 355(1). According to a classification scheme(2), this Koc value suggests that 2,5-dichloroaniline is expected to have moderate mobility in soil. However, when released to soil containing humic material, 2,5-dichloroaniline may undergo a covalent chemical bonding resulting in its chemical alteration to a latent form resulting in strong adsorption(3). |
| Artificial Pollution Sources | 2,5-Dichloroaniline's production and use as a dye intermediate(1) may result in its release to the environment through various waste streams(SRC). Aromatic amines such as 2,5-dichloroaniline are introduced into the environment directly as industrial effluents and indirectly as transformation products from pesticides or pharmaceuticals(2). 2,5-Dichloroaniline has been identified as a degradation product of Acid Dye 13155(3). |
| Environmental Biodegradation | The effects of dichlorine-substituted anilines on Guelph loam were studied. 2,5-Dichloroaniline at concentrations of 5 to 100 ug/g soil was inhibitory against the oxidation of the nitrogen of ammonia to nitrite nitrogen, but not nitrite nitrogen to nitrate nitrogen. It showed almost a linear rate of decomposition over the 12 wk period of the expt. The dichloroanilines were more persistent than aniline or the monochloroanilines.2,5-Dichloroaniline demonstrated almost a linear rate of decomposition in Guelph loam over a 12 week period, with a half-life of 8 weeks(1). 2,5-Dichloroaniline has been classified as resistant to biodegradation (theoretical BOD of less than 30% over a 14-day incubation period using an activated sludge inocula) using the Japanese MITI test protocol(2-4). 2,5-Dichloroaniline, present at 100 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(5). Using the modified OECD Screening Test (activated sludge inocula, 28 days aerobic incubation), less than 25% of initial 2,5-dichloroaniline was degraded based on DOC analysis(6). Using the modified AFNOR Test (28 days of incubation), 7% of initial 2,5-dichloroaniline was degraded based on DOC analysis(6). |
| Environmental Bioconcentration | An estimated BCF of 35 was calculated for 2,5-dichloroaniline(SRC), using log Kow of 2.92(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate. |
| Volatilization from Water/Soil | The Henry's Law constant for 2,5-Dichloroaniline is estimated as 1.6X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,5-dichloroaniline is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 30 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 219 days(SRC). However, the volatilization half-life does not take into account the effects of adsorption. A Koc of 355(3) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 662 days in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 317 days in a model pond 2 m deep(4). 2,5-Dichloroaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2,5-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-2 mm Hg(SRC), determined from a fragment constant method(5). |
| Non-Human Toxicity Excerpts | IN GUELPH LOAM, 2,5-DICHLOROANILINE, AT CONCN OF 5-100 UG/G SOIL, WAS INHIBITORY AGAINST THE OXIDN OF THE NITROGEN OF AMMONIA TO NITRITE NITROGEN BY NITROSOMONAS, BUT NOT NITRITE NITROGEN TO NITRATE. THE DICHLOROANILINES SHOWED INCREASED TOXICITY AGAINST NITROSOMONAS.TWENTY-ONE HALO-SUBSTITUTED ANILINES WERE COMPARED WITH ANILINE FOR THEIR ABILITY TO STIMULATE METHEMOGLOBIN FORMATION IN CATS. HALO SUBSTITUTIONS IN THE 4-POSITION INCREASED THE ACTIVITY OF ANILINE, WHILE SUBSTITUTIONS IN THE 2 AND 3 POSITIONS DID NOT CHANGE OR REDUCE THE ACTIVITY. POLYHALO SUBSTITUENTS (SUCH AS 2,6-DICHLOROANILINE) REDUCED THE ACTIVITY COMPARED TO ANILINE. /DICHLOROANILINES/Dichloroaniline produces methemoglobinemia in rats & mice. /Dichloroaniline/ |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 2,5-dichloroaniline with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 2,5-dichloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum. |
| F | 8 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | BX2610000 |
| 輸送番号（UN） | UN 3442 6.1/PG 2 |
| PRTR法 | 第一種指定化学物質 |
| 税関コード | 29214210 |
| 危険文句（R） | 23/24/25-33-50/53 |
| 化審法 | (3)-261 |
| 危険表示 | T,N |
| hazard_note | Toxic |
| 安全措置（S） | 28-36/37-45-60-61-28A |
| 危険等級 | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2 |
| 包装等級 | II |
| 自然発火温度 | >374 °F |
| 環境リスク評価 | 2,5-ジクロロアニリン(95-82-9) |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 有害物質データ | 95-82-9(Hazardous Substances Data) |
用途
用途
染料?顔料中間体
使用
2,5-Dichloroaniline is used as an intermediate in the synthesis of dyestuffs, pigments, and pesticides.
一般的な説明
Brown crystalline solid.