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邻氯苯胺
邻氯苯胺 · 邻氨基氯苯 · 2-氯苯胺 · 曲唑酮杂质23 · 2氯苯胺/GC · 邻氯苯胺(冷库) · 2-氯苯胺 溶液 · 乙腈中2-氯苯胺
标识与物理属性
| CAS No. | 95-51-2 |
|---|---|
| 分子式 | C6H6ClN |
| 平均分子量 | 127.57 g/mol |
| 单同位素质量 | 127.01887687 g/mol |
| SMILES | Nc1ccccc1Cl |
| InChIKey | AKCRQHGQIJBRMN-UHFFFAOYSA-N |
| PubChem CID | 7240 |
| ChEMBL | CHEMBL389885 |
| EC No. | 202-426-4 |
| DTXSID | DTXSID2021810 |
| 中文名 | 邻氯苯胺 |
化学与物理性质
| XLogP | 1.9 |
|---|---|
| 极性表面积 | 26 |
| 氢键供体 | 1 |
| 氢键受体 | 1 |
| 可旋转键 | 0 |
| 重原子 | 8 |
| 形式电荷 | 0 |
| 复杂度 | 74.9 |
| 物质类别 | Nitrogen Compounds -> Amines, AromaticTextile |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP（油水分配系数） | log Kow = 1.901.921.74 |
| 气味 | Characteristic sweet odorAmine odorCharacteristic odour |
| 密度 | 1.213 at 68 °F (NTP, 1992) - Denser than waterwill sink1.2114 at 22 °C/4 °C1.213 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.001.213 g/mL at 25 °C(lit.) |
| Viscosity | 2.9157 cP at 20 °C |
| Color/Form | Amber liquidWater-white to tan liquidColorless liquid |
| 溶解性 | less than 1 mg/mL at 68 °F (NTP, 1992)Soluble in acid and in most organic solvents.Miscible in alcohol and etherSoluble in alcohol, ether, benzene, and acetone.In water, 8165 mg/L at 25 °CSolubility in water, g/100ml at 20 °C: 0.5water: soluble5.13g/L at 20°C5.13 g/L (20 ºC) |
| 闪点 | 208 °F (NTP, 1992)103 °C103 °C (closed cup)108 °C98 °C |
| 沸点 | 406 to 410 °F at 760 mmHg (NTP, 1992)208.8 °C209 °C208-210 °C(lit.) |
| Decomposition | When heated to decomposition, it emits toxic fumes of /hydrogen chloride and nitrogen oxides/. |
| 熔点 | 28.5 °F (NTP, 1992)-14 °C-2 °C0-3 °C |
| 蒸气密度 | 4.41 (vs air) |
| 蒸气压 | 0.5 hPa (20 °C) |
| 折射率 | n20/D 1.589 |
| 储存条件 | Store below +30°C. |
| 形态 | Liquid |
| pKa（酸度系数） | 2.65(at 25℃) |
| 颜色 | Clear pale yellow to brown |
| 爆炸极限 | 2.4-14.2%(V) |
| 热导率 | 0.148 W/(m·K) at 25 ℃ |
| Merck | 14,2118 |
| BRN | 606077 |
| 亨利常数 | 1.9×100 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 介电常数 | 13.4 |
| InChI | 1S/C6H6ClN/c7-5-3-1-2-4-6(5)8/h1-4H,8H2 |
| InChIKey | AKCRQHGQIJBRMN-UHFFFAOYSA-N |
| SMILES | Nc1ccccc1Cl |
| LogP（油水分配系数） | 1.72 at 20℃ and pH6-8 |
| CAS 数据库 | 95-51-2(CAS DataBase Reference) |
| NIST化学物质信息 | o-Chloroaniline(95-51-2) |
| EPA化学物质信息 | o-Chloroaniline (95-51-2) |
化学性质
琥珀色液体，有氨臭。暴露在空气中颜色变黑。 几乎不溶于水，溶于酸和大多数常用有机溶剂。
安全与法规
| GHS 分类 | DangerH301+H311+H331 (78.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P337+P317, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 204 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 法规信息 | Chemical: Benzenamine, 2-chloro-Benzenamine, 2-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 2-chloro- 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: 15-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/137852-Chloroaniline: Does not have an individual approval but may be used under an appropriate group standard |
| 其他安全信息 | IMAP assessments - 2-Chloroaniline and its hydrochloride: Human health tier II assessment |
| 运输标签（DOT） | Poison |
| 火灾危害 | This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 健康危害 | SYMPTOMS: Symptoms of exposure to this compound may include headache, nausea, vomiting, jaundice, convulsions, severe kidney damage, liver damage, methemoglobin formation and in sufficient concentrations, cyanosisskin and eye irritationand dermatitis. Onset may be delayed 2-4 hours or longer. |
| 危害概述 | o-Chloroaniline is listed in a table Examples of Industrial Chemicals for Which Methemoglobin Formation is the Principal Cause of Toxicity[ACGIH] In the United Kingdom between 1961 and 1980, chloroaniline, p-toluidine, nitrobenzene, and nitrochlorobenzene were the most common industrial causes of methemoglobinemia. Dermal exposure was a more frequent route of toxicity than inhalation with these compounds. (Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988.) An eye irritantCan induce methemoglobinemia[ICSC] Negative results for skin sensitizer from guinea pig testing[Reference #2] |
| 反应性基团 | Aryl Halides |
| 欧共体分类 | Symbol: T, NR: 23/24/25-33-50/53S: (1/2)-28-36/37-45-60-61Note: C |
| 联合国分类 | UN Hazard Class: 6.1UN Pack Group: II |
| TSCA 要求 | 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. Benzenamine, 2-chloro- is included on this list. |
| Reactivity Profile | O-CHLOROANILINE is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. (NTP, 1992) |
| 大气标准 | 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. o-chloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart. |
| 消防 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use powder. Use foam. Use carbon dioxide. |
| 急救措施 | 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 . |
| 急救 | 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. |
| 安全储存 | Separated from food and feedstuffs. Keep in the dark. Well closed. |
| 暴露控制与个人防护 | Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or end of shift |
| 灭火程序 | Water, dry chemical, foam or carbon dioxide /4-chloroaniline/ |
| 非火灾泄漏应对 | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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. |
| 处置方法 | 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. |
| 泄漏处置 | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | Immediately wash contaminated areas of body with concentrated soap solution. Remove contaminated clothing, dry, then wash with concentrated soap solution or dispose as waste. Contaminated shoes may be disposed in an incinerator.Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Isolation and Evacuation | Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: |
| Eye Prevention | Wear safety goggles or face shield. |
| 生态毒性数值 | EC50 Daphnia magna (Daphnidsability to swim) 4.2 mg/L/24 hr /Conditions of bioassay not specified in source examined/ability to swim) 1.8 mg/L/48 hr /Conditions of bioassay not specified in source examined/LC50 Tubifex (Worm) 130-220 mg/L/48 hrLC50 Oryzia latipes (Medaka) 6.4 mg/L/48 hr /Conditions of bioassay not specified in source examined/For more Ecotoxicity Values (Complete) data for 2-CHLOROANILINE (9 total), please visit the HSDB record page. |
| 环境归趋 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 260(SRC), determined from a log Kow of 1.90(2) and a regression-derived equation(3), indicates that 2-chloroaniline is expected to have moderate 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(4,5), suggesting that mobility may be much lower in some soils(SRC). The pKa of 2-chloroaniline is 2.66(6), indicating that this compound will primarily exist in its nonionic form in the environment. Volatilization of 2-chloroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.20 mm Hg(7), and water solubility, 8.2X10+3 mg/L(8). However, adsorption to soil is expected to attenuate volatilization(SRC). 2-Chloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.20 mm Hg(7). Biodegradation screening tests suggest that 2-chloroaniline is slightly to non-biodegradable(9,10). 100% loss of UV absorbance by microbial degradation in a mineral salts solution, with a soil inoculum, required an excess of 64 days(11). When 2-chloroaniline (3-ppm) was incubated in Guelph loam with water added to 60% water-holding capacity, levels declined rapidly for 2 weeks after which time the rate of loss decreased(12). The percent of 2-chloroaniline remaining in soil after 2 and 8 weeks were 40 and 20%, respectively(12). Experiments using 2-chloroaniline show that it undergoes photolysis in aqueous solution when irradiated by light with wavelengths above 290 nm (13,14)2-chloroaniline may also be susceptible to direct photolysis by sunlight in soil surfaces(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 260(SRC), determined from a log Kow of 1.90(2) and a regression-derived equation(3), indicates that 2-chloroaniline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.20 mm Hg(4), and water solubility, 8.2X10+3 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.8 days and 60 days, respectively(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic group(6,7), and volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The pKa of 2-chloroaniline is 2.66(8), indicating that this compound will primarily exist in its nonionic form in the environment. According to a classification scheme(9), an estimated BCF of 5.8(SRC), from an estimated log Kow(2) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation screening tests suggest that 2-chloroaniline is generally resistant to biodegradation or biodegrades slowly(11,12). 2-Chloroaniline (2 mg/L) was found to be not readily biodegradable with a 10% BOD observed after 5 days in a mixed inoculum of river water collected from the Songhua River in China(13). Irradiation of an aqueous solution of 2-chloroaniline in a quartz tube with a fluorochemical lamp (wavelengths above 300 nm) resulted in a photodegradation half-life of 11.5 hours(14). When aqueous solutions of 2.5X10-3 mol/L 2-chloroaniline in a photochemical reactor were irradiated by a mercury lamp (wavelengths 254, 297, and 365 nm), the concentration of 2-chloroaniline decreased exponentially with time, and the rate of disappearance approximated a first-order process with a rate constant of 0.107/hour(15).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-chloroaniline, which has a vapor pressure of 0.20 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-chloroaniline 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 12 hours(SRC), calculated from its rate constant of 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Chloroaniline absorbs ultraviolet light above 290 nm(4). Experiments using 2-chloroaniline show that it undergoes photolysis in aqueous solution when irradiated by light with wavelengths above 290 nm (5,6)2-chloroaniline may also be susceptible to direct photolysis by sunlight in air(SRC). |
| 食品调查数值 | 2-Chloroaniline has been qualitatively identified as a volatile flavor component of Idaho Russet baked potatoes(1). |
| 不良影响 | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as primary toxic effect. |
| 暴露途径 | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. |
| 生态毒性摘录 | /AQUATIC SPECIES/ 21 day Daphnia reproduction tests were conducted in line with the provisional procedure proposed by the Federal Environmental Agency (Umweltbundesamt, FRG), as of Jan 1, 1984. Groups of 20, 24-hr old Daphnia magna Straus were exposed to 0.001 to 3.16 mg/L 2-chloroaniline in semi-static test vessels. Parent animals in the test and control vessels had to be pipetted 3 times/wk in freshly prepared test and control media at the corresponding concentration level. The no observed effect concentration (NOEC) was determined from the parameters of mortality of the parent animals, reproduction rate and appearance of the first offspring during the test period. In preliminary acute Daphnia tests, the 24-hr EC50 was 6.0 mg/L for 2-chloroaniline, the EC0 was 1.4 mg/L. The nominal 21-day no observed effect concentration was 0.032 mg/L./AQUATIC SPECIES/ Twenty-nine day old fathead minnows were exposed to an 80 mg/L concentration of 2-chloroaniline. Test conditions were as follows: Exposure temperature: 24.9 °CpH: 7.60. Average concentration/chamber of 2-chloroaniline ranged from 2.00-25.9 mg/L. Affected fathead minnows lost schooling behavior and swam near the tank surface. They were hyperactive and overreactive to external stimuli, were darkly colored, and hemorrhagic. Equilibrium loss was not observed prior to death. |
| Signs and Symptoms | Blue lips, fingernails and skin. Dizziness. Headache. Shortness of breath. Nausea. Vomiting. Convulsions. Weakness. Confusion. Unconsciousness.MAY BE ABSORBED! Further see Inhalation.Redness. Pain.Abdominal pain. Further 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. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=95-51-2] |
| Effluent Concentrations | 2-Chloroaniline was detected at an average concentration of 42.58 ug/L and a 76.5% frequency of detection in sewage treatment effluents in England and Wales collected in 1995(1). In a comprehensive survey of wastewater from 4,000 industrial and publicly owned treatment works sponsored by the Effluent Guidelines Division of the US EPA, 2-chloroaniline was identified in discharges of the following industrial categories (positive occurrences, median concentration in ppb): pharmaceuticals (4588.1) and organic chemicals (357.1)(2). The highest effluent concentration was 2564.1 ppb in the pharmaceutical industry(2). Wastewater discharges from the commercial manufacture of 4,4'-methylenebis(2-chloroaniline) can contain 2-chloroaniline(3). 2-Chloroaniline was qualitatively detected in effluent discharges from chemical production facilities along the Upper Catawba River in North Carolina in 1973 and 1974(4). Sludge from the Muskegon County, Michigan wastewater treatment system was found to contain 48.3 mg/kg 2-chloroaniline(5). |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. |
| Medical Surveillance | Consider the points of attack (blood, heart, lung and liver) in preplacement and periodic physical examinations. /4-Nitroaniline/ |
| Soil Adsorption/Mobility | The Koc of 2-chloroaniline is estimated as 260(SRC), using a log Kow of 1.9(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-chloroaniline is expected to have moderate 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(4,5), suggesting that mobility may be much lower in some soils(SRC). |
| F | 8-10-23 |
| 水危害等级（WGK） | 2 |
| TSCA 清单状态 | TSCA listed |
| RTECS 号 | BX0525000 |
| 包装类别 | II |
| 危险类别 | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Muta. 2STOT RE 2 |
| 储存类别 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 安全说明（S） | 28-36/37-45-60-61-28A-16 |
| 海关编码 | 29214210 |
| 自燃温度 | >500 °C |
| 危险品标志 | T,N,F |
| 危险类别码（R） | 23/24/25-33-50/53-39/23/24/25-11-52/53 |
| 毒害物质数据 | 95-51-2(Hazardous Substances Data) |
| 运输编号（UN） | UN 2019 6.1/PG 2 |
急性毒性
口服- 小鼠 LD50: 256 毫克/ 公斤
可燃性危险特性
明火可燃; 高热放出有毒氯化物及氮氧化物气体
储运特性
库房通风低温干燥; 与氧化剂、酸类、食品添加剂分开存放
灭火剂
雾状水、泡沫、二氧化碳、干粉
用途与应用
应用
邻氯苯胺具有较好的化学稳定性和生物活性，在药物和农药分子的结构修饰和合成中得到广泛应用。在药物合成中，邻氯苯胺可以用作药物分子的中间体，通过改变它的结构和性质来改善药物的药效和药代动力学特性。在农药生产中，邻氯苯胺也被广泛应用于杀虫剂和除草剂等农药的合成。
用途
邻氯苯胺是除草剂绿磺隆的原料，也是重要的染料中间体，在染料工业中，用于冰染染料色基。还用于农药、医药、合成树脂，有机合成等领域。
用途
该品为冰染染料色基，亦可作为偶氮染料的重氮组分，用于生产酸性黑、酸性蓝及有机色淀水固黄R、永固红FR、汉沙黄HR等。并可用于制取医药、农药、聚氨酯树脂的交联剂甲基双氯苯胺。
制备与合成方法
生产方法
由邻硝基氯苯还原而得：在盐酸介质中用铁粉还原，回流6-8h，经水蒸汽蒸馏、减压蒸馏得成品。也可以在甲酸存在下进行铁粉还原：在10m3的铸铁还原釜中加入2m3沸水，然后加入邻硝基氯苯100kg、甲酸15kg、铁粉1.5t，进行还原反应。在17-20h内分次加入4t邻硝基氯苯。其间，在还原反应进行到一刻钟时，加入1t邻硝基氯苯，同时加入铁粉1.5t和甲酸15kg。如果反应缓慢，可再加入铁粉1t。反应完成后，静置，分离出胺层，再静置，使铁沉淀，铁渣用水蒸汽蒸馏出胺。将粗品减压蒸馏，得邻氯苯胺3160kg，收率95%。原料消耗定额：邻硝基氯苯1300kg/t、铁粉（90%）1450kg/t、盐酸（37%） 380kg/t。
生产方法
其制备方法是用邻氯硝基苯与铁屑、稀盐酸和水回流6～8h，蒸馏得粗品，再蒸馏得成品。或者用催化加氢的方法，也就是以邻氯硝基苯为原料，在催化剂存在下加氢而制得成品。