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2-クロロアニリン

2-Chloroaniline

HCID 7240
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
95-51-2
標準SMILES
Nc1ccccc1Cl
InChIKey
AKCRQHGQIJBRMN-UHFFFAOYSA-N
分子式
C6H6ClN
平均分子量
127.57 g/mol
単同位体質量
127.01887687

概要

O-chloroaniline is a clear amber liquid with an amine odor. Occurs in both alpha and beta forms. (NTP, 1992)

名称と識別子

優先名称
2-Chloroaniline
IUPAC
2-chloroaniline
現地名
2-クロロアニリン
英語名
2-Chloroaniline
分子式
C6H6ClN
分子量
127.57

名称と別名

2-CHLOROANILINE95-51-2o-Chloroaniline1-Amino-2-chlorobenzene2-ChlorophenylamineBenzenamine, 2-chloro-Fast Yellow GC Baseo-AminochlorobenzeneAniline, o-chloro-o-Chloroaminobenzeneo-ChloranilineDTXSID2021810
名称をさらに表示
2-クロロアニリンC.I.アゾイックジアゾコンポーネント44【ベース】2-クロロベンゼンアミンファーストイエローGCベースミツイイエローGCベースo-クロロアニリンファーストイエローベースGCアゾイックDC44(ベース)カコーイエローGCベース2-クロロベンゼン-1-アミンC.I.アゾイックジアゾコンポーネント44(ベース)2-クロロフェニルアミンoクロロアニリンO‐クロロアニリン2-クロロアニリン, 98+%1-アミノ-2-クロロベンゼンOCA2-CHLOROANALINE2-Chloranilin2-Chloroanlineo-chloro-anilin
2-Amino-1-chlorobenzeneG14I494T2FNSC-6183DTXCID001810RefChem:86446202-426-42-ChlorobenzenamineNSC 6183

データベース識別子

CAS
95-51-2
PubChem CID
7240
DTXSID
DTXSID2021810
ChEMBL
CHEMBL389885
UNII
G14I494T2F
EC Number
202-426-4
Nikkaji
J2.759.603G、J3.952G

物性

構造計算による物性

XLogP
1.9
極性表面積
26 Ų
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
8
形式電荷
0
複雑度
74.9

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Amines, Aromatic

Textile

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 3 件

log Kow = 1.90

1.92

1.74

Odor · 2 件

Characteristic sweet odor

Amine odor

Density · 4 件

1.213 at 68 °F (NTP, 1992) - Denser than water; will sink

1.2114 at 22 °C/4 °C

1.213 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

Viscosity2.9157 cP at 20 °C
Color/Form · 3 件

Amber liquid

Water-white to tan liquid

Colorless liquid

Solubility · 6 件

less than 1 mg/mL at 68 °F (NTP, 1992)

Soluble in acid and in most organic solvents.

Miscible in alcohol and ether

Soluble in alcohol, ether, benzene, and acetone.

In water, 8165 mg/L at 25 °C

Solubility in water, g/100ml at 20 °C: 0.5

Flash Point

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H301+H311+H331 (78.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute 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.

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory Information · 4 件

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/13785

2-Chloroaniline: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Chloroaniline and its hydrochloride: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 件

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health Hazards · 1 件

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, cyanosis; skin and eye irritation; and dermatitis. Onset may be delayed 2-4 hours or longer.

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

o-Chloroaniline in rabbits is metabolized to 2-amino-3-chlorophenol and 4-amino-3-chlorophenol. In soya beans it yields o-chloroaniline-n-glucoside. /from table/

Bacillus firmus was isolated and transformed 2-chloroaniline almost quantitatively into 4-chloroacetanilide with smaller amount of 4-chloropropionanilide according to co-metabolic reaction.

The primary metabolite of either 2-chloroaniline or 4-chloroaniline by a faecalis in a liquid culture was 4-chloropyrocatechin, further metabolized to 5-chloro-2-hydroxymuconic acid semialdehyde, which was in turn metabolized with the NAD+ cosubstrate to 2-chloro-4-oxalocrotonic acid.

Studies in rats and rabbits have shown that like other aromatic amines, the compound is oxidized in microsomes of liver, kidney, and lung by cytochrome P450 oxidases to its hydroxylated derivatives, which undergo N-acetylation and/or conjugation with glucuronic and sulfuric acids, with subsequent excretion in the urine and/or dissociation into reactive metabolites in the bladder of some species such as the dog and the human.

For more Metabolism/Metabolites (Complete) data for 2-CHLOROANILINE (7 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 2 件

The compound is absorbed through the intact skin. o-Chloroaniline is absorbed by oral, inhalation, or dermal exposure.

... Male Fischer 344 rats (4/group) were administered [14C]-2-chloroaniline or [14C]-4-chloroaniline (0.5 or 1.0 mmol/kg; approximately 50 uCi/rat) ip. Urine, feces, blood and tissues were collected at 3 and 24 hr. Both 2- and 4-chloroaniline-derived radioactivity were primarily renally excreted with <1% excretion in the feces by 24 hr post-treatment. Both chloroanilines accumulated mainly in liver (percentage of administered dose/total tissue), but kidney generally had similar or higher equivalent concentrations (umol/g tissue) compared to liver. Subcellular distribution revealed that for both chloroanilines, the cytosolic fraction generally had the highest level of radioactivity independent of time or dose. Covalent binding was detected in both liver and kidney, with the highest concentration (pmol/mg protein) of binding observed in the hepatic microsomal fraction regardless of compound, dose or time studied. In general, 2-chloroaniline derived radioactivity was excreted faster, reached peak tissue concentrations earlier, disappeared from tissues faster and had less covalent binding in target tissue at 24 hr than 4-chloroaniline-derived radioactivity.

関連反応

460 件
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HRID 241反応物として750 AstraZeneca ELN dataset
HRID 250 の反応式
HRID 250反応物として750 AstraZeneca ELN dataset
HRID 20648 の反応式
HRID 20648反応物としてuspto-grants-2010_06
HRID 21670 の反応式
HRID 21670反応物としてuspto-grants-1995_06
HRID 23385 の反応式
HRID 23385反応物としてuspto-grants-2005_02
HRID 23387 の反応式
HRID 23387反応物としてuspto-grants-2005_02
HRID 26362 の反応式
HRID 26362反応物としてuspto-grants-1979_04
HRID 28622 の反応式
HRID 28622反応物としてuspto-grants-2008_09
1 / 58 ページ

化合物ノート

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その他の操作
ノートを作成反応を作成見積依頼を出す
· 4 件

208 °F (NTP, 1992)

103 °C

103 °C (closed cup)

108 °C

Boiling Point · 3 件

406 to 410 °F at 760 mmHg (NTP, 1992)

208.8 °C

209 °C

DecompositionWhen heated to decomposition, it emits toxic fumes of /hydrogen chloride and nitrogen oxides/.
Melting Point · 3 件

28.5 °F (NTP, 1992)

-14 °C

-2 °C

物理化学的性質

融点
0 · 0-3 °C
沸点
208 · 208-210 °C(lit.)
比重(密度)
1.213 g/mL · 1.213 g/mL at 25 °C(lit.)
蒸気密度
4.41 · 4.41 (vs air)
蒸気圧
0.5 hPa · 0.5 hPa (20 °C)
屈折率
20 · n20/D 1.589
闪点
98 °C · 98 °C
貯蔵温度
30 °C · Store below +30°C.
溶解性
20 ℃で可溶5.13g/L · 水:20℃で可溶5.13g/L
外見
液体
酸解離定数(Pka)
2.65 · 2.65(at 25℃)
色
澄んだ淡黄色~褐色
臭い (Odor)
特有の臭い
爆発限界(explosive limit)
2.4 · 2.4-14.2%(V)
水溶解度
5.13 g/L · 5.13g/L(20℃)
Merck
14 · 14,2118
BRN
606077 · 606077
Henry's Law Constant
1.9 · 1.9×100 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
13.4 · 13.4
InChI
1S/C6H6ClN/c7-5-3-1-2-4-6(5)8/h1-4H,8H2
InChIKey
AKCRQHGQIJBRMN-UHFFFAOYSA-N
SMILES
Nc1ccccc1Cl
LogP
1.72 at · 1.72 at 20℃ and pH6-8
CAS データベース
95 · 95-51-2(CAS DataBase Reference)
NISTの化学物質情報
o-Chloroaniline(95-51-2)
EPAの化学物質情報
o-Chloroaniline (95-51-2)

化学的性質

化学的特性clear pale yellow to brown liquid with ammonia odor. darkens on exposure to air. almost insoluble in water, soluble in acids and most common organic solvents.

Hazards Summary · 1 件

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 irritant; Can induce methemoglobinemia; [ICSC] Negative results for skin sensitizer from guinea pig testing; [Reference #2]

Reactive GroupAryl Halides
EC ClassificationSymbol: T, N; R: 23/24/25-33-50/53; S: (1/2)-28-36/37-45-60-61; Note: C
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
TSCA Requirements · 1 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. Benzenamine, 2-chloro- is included on this list.

Reactivity ProfileO-CHLOROANILINE is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. (NTP, 1992)
Atmospheric Standards · 1 件

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.

安全と保護具

Fire Fighting · 2 件

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.

First Aid Measures · 4 件

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 .

First Aid · 1 件

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.

Safe StorageSeparated from food and feedstuffs. Keep in the dark. Well closed.
Exposure Control and Personal ProtectionBiological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or end of shift
Fire Fighting ProceduresWater, dry chemical, foam or carbon dioxide /4-chloroaniline/
Nonfire Spill Response · 1 件

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.

Disposal Methods · 1 件

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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 件

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 · 3 件

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 EvacuationExcerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Eye PreventionWear safety goggles or face shield.

毒性情報

Ecotoxicity Values · 5 件

EC50 Daphnia magna (Daphnids; ability to swim) 4.2 mg/L/24 hr /Conditions of bioassay not specified in source examined/

EC50 Daphnia magna (Daphnids; 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 hr

LC50 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.

Environmental Fate · 3 件

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).

Food Survey Values2-Chloroaniline has been qualitatively identified as a volatile flavor component of Idaho Russet baked potatoes(1).
Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as primary toxic effect.
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Ecotoxicity Excerpts · 2 件

/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 °C; pH: 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 · 4 件

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 · 1 件

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 · 1 件

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 (4; 588.1) and organic chemicals (3; 57.1)(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 DataThe substance is toxic to aquatic organisms.
Medical SurveillanceConsider the points of attack (blood, heart, lung and liver) in preplacement and periodic physical examinations. /4-Nitroaniline/
Soil Adsorption/Mobility · 1 件

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).

法規制情報

TSCA Requirements · 1 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. Benzenamine, 2-chloro- is included on this list.

Atmospheric Standards · 1 件

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.

安全データ

F
8-10-23
wgk
2
tsca
TSCA listed
rtecs
BX0525000
ridadr
UN 2019 6.1/PG 2
PRTR法
第一種指定化学物質
hs_code
29214210
risk_code
23/24/25-33-50/53-39/23/24/25-11-52/53
化審法
(3)-194 優先評価化学物質
消防法
危-4-3-III
hazard_code
T,N,F
safety_code
28-36/37-45-60-61-28A-16
hazard_class
6.1
packing_group
II
毒劇物取締法
劇物
自然発火温度
>500 °C
環境リスク評価
o-クロロアニリン(95-51-2)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Muta. 2STOT RE 2
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
有毒物質データの
95-51-2(Hazardous Substances Data)

用途と製造

Uses · 3 件

Used as an intermediate for dyes, pesticides, and rubber chemicals; [HSDB]

... Intermediate for rubber chemicals, pigments, pesticides and dyes.

Dye intermediate, standards for colorimetric apparatus, manufacture of petroleum solvents and fungicides.

U.S. Production2020: 41,888 lb
Industry UsesIntermediate
Methods of ManufacturingProduction is by low-pressure hydrogenation of 2-chloronitrobenzene with noble metal and/or noble metal sulfide catalysts at temperatures of about 50-100 °C in inert organic solvents.
Formulations/Preparations · 2 件

GRADES:Technical

Liquid, technical grades

General Manufacturing Information · 2 件

Synthetic Rubber Manufacturing

Benzenamine, 2-chloro-: ACTIVE

応用分野 · 3 件

用途有機合成原料(染料、医薬、農薬)。

使用2-Chloroaniline used as petroleum solvents. It is used in biological studies to evaluate the mutagenicity and carcinogenicity of Salmonella typhimurium. Used as a Intermediates for dyestuff, pigment and specialty chemicals. 2-Chloroaniline is widely used in polymer, rubber, pharmaceutical and dye industries.

一般的な説明Clear amber liquid with an amine odor. Occurs in both alpha and beta forms.

調製方法 · 2 件

製造方法The synthesis method of 2-chloroaniline is to reflux 2-nitrochlorobenzene with iron filings, dilute hydrochloric acid and water for 6~8h, distill to get crude product, and then distill to get finished product.

純化方法Free it from small amounts of the p-isomer by dissolving in one equivalent of H2SO4 and steam distilling. The p-isomer remains behind as the sulfate. [Sidgwick & Rubie J Chem Soc 1013 1921.] An alternative method is to dissolve it in warm 10% HCl (11mL/g of amine) and on cooling, o-chloroaniline hydrochloride separates out. The latter can be recrystallised until the acetyl derivative has a constant melting point (m 90o). (In this way, yields are better than via the recrystallisation of the picrate from EtOH or of the acetyl derivative from pet ether.) [King & Orton J Chem Soc 1377 1911]. [Beilstein 12 III 1281, 12 IV 1115.]

上流・下流製品情報

上流原料

Iron filings2-クロロニトロベンゼン鉄粉

下流製品

fluorescent whitening agent JD-34'-ブロモ-2'-クロロアセトアニリド8-クロロキノリン4,4'-メチレンビス(2-クロロアニリン)5-[4-クロロ-6-(メチルフェニルアミノ)-1,3,5-トリアジン-2-イルアミノ]-4-ヒドロキシ-3-[2-(ソジオスルホ)フェニルアゾ]-2,7-ナフタレンジスルホン酸ジナトリウム2-ブロモクロロベンゼン8-Chloro-2-(trifluoromethyl)quinoline-4-carbonitrile1-(4-ピペリジニル)-1,3-ジヒドロ-2H-ベンゾイミダゾール-2-オンイソシアン酸 2-クロロフェニル1-(o-クロロフェニル)チオ尿素2-クロロベンゼンスルホンアミド4-クロロ-2-オキソ-3-ベンゾチアゾリン酢酸o-フェネチジンN-(2,5-ジメトキシフェニル)-2-ヒドロキシ-3-ジベンゾフランカルボアミド2-(ジシクロヘキシルホスフィノ)-2'-(ジメチルアミノ)ビフェニル4,6-ジクロロ-N-(o-クロロフェニル)-1,3,5-トリアジン-2-アミン1-[(o-クロロフェニル)スルホニル]-3-(4-メトキシ-6-メチル-1,3,5-トリアジン-2-イル)尿素2'-クロロアセトアニリド2-クロロアニリン 塩酸塩1,3-ジクロロベンゼン2'-クロロアセトアセトアニリドo-ジクロロベンゼン2-クロロベンゼンスルホニルクロリド