m-アニシジン

3-Methoxyaniline

HCID 10824CAS 536-90-3

基本情報

標準SMILES
COc1cccc(N)c1
InChIKey
NCBZRJODKRCREW-UHFFFAOYSA-N
分子式
C7H9NO
平均分子量
123.15 g/mol
単同位体質量
123.06841391

名称と識別子

優先名称
3-Methoxyaniline
IUPAC
3-methoxyaniline
現地名
m-アニシジン
英語名
m-Anisidine
分子式
C7H9NO
分子量
123.15

名称と別名

m-Anisidine3-METHOXYANILINE536-90-3m-Methoxyaniline3-Aminoanisole3-MethoxybenzenamineBenzenamine, 3-methoxy-m-Aminoanisolem-Anisylamine1-Amino-3-methoxybenzene3-methoxyphenylamineDTXSID8024529
名称をさらに表示
m-アニシジン3-メトキシベンゼン-1-アミン3-メトキシベンゼンアミン1-メトキシ-3-アミノベンゼンm-アミノアニソール3-メトキシアニリンm-メトキシアニリン3-アニシジン1-アミノ-3-メトキシベンゼンmアニシジン3‐アニシジン(3‐メトキシアニリン)標準品M‐アニシジンm-アニシジン, 98%3-アニシジン(3-メトキシアニリン)標準品m-アニシジン標準品META-ANISIDINEJABJMJAJBJMm-Anisidinm-anisidien
JXA144KX2Im-AminomethoxybenzeneNSC-76313-Aminophenol methyl etherDTXCID604529RefChem:154857208-651-43-Anisidine

データベース識別子

CAS
536-90-3
PubChem CID
10824
DTXSID
DTXSID8024529
ChEMBL
CHEMBL1500995
ChEBI
CHEBI:194944
UNII
JXA144KX2I
EC Number
208-651-4
Nikkaji
J1.593H

物性

構造計算による物性

XLogP
0.9
極性表面積
35.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
1
重原子数
9

実験および物理化学的性質

LogP · 2 件

log Kow = 0.93

0.93

Density · 2 件

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

1.1 g/cm³

Color/FormPale yellow, oily liquid
Solubility · 3 件

less than 1 mg/mL at 66 °F (NTP, 1992)

Slightly soluble in carbon tetrachloride; soluble in ethanol, ethylene, acetone, benzene

Solubility in water, g/100ml at 20 °C: 2.05

Flash Point · 3 件

greater than 235 °F (NTP, 1992)

126 °C (259 °F) - closed cup

>112 °C

Boiling Point · 3 件

484 °F at 760 mmHg (NTP, 1992)

251 °C

251 °C

物理化学的性質

融点
1 · −1-1 °C(lit.)
沸点
251 °C · 251 °C(lit.)
比重(密度)
1.096 g/mL · 1.096 g/mL at 25 °C(lit.)
屈折率
20 · n20/D 1.581(lit.)
闪点
230 °F · >230 °F
貯蔵温度
2 · 2-8°C

化学的性質

化学的特性Light yellow oily liquid with have characteristic amine (fishy) odors. soluble in alcohol, ether, benzene and dilute acid, slightly soluble in water. Anisidine exists as ortho-, meta-, and paraisomers.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H301+H311+H331 (39%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation];H301 (40.3%): Toxic if swallowed [Danger Acute toxicity, oral];H302 (59.7%): Harmful if swallowed [Warning Acute toxicity, oral];H311 (45.5%): Toxic in contact with skin [Danger Acute toxicity, dermal];H315 (93.5%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (93.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H331 (40.3%): Toxic if inhaled [Danger Acute toxicity, inhalation];H335 (55.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H371 (37.7%): May cause damage to organs [Warning Specific target organ toxicity, single exposure];H372 (36.4%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure];H400 (98.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (98.7%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P308+P316, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 77 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 3 件

Chemical: Benzenamine, 3-methoxy-

Status: Active Update: 01-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20544

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

DOT LabelPoison
Fire Hazards · 2 件

This chemical is probably combustible. (NTP, 1992)

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

Fire PotentialCombustible
Health Hazards · 1 件

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Other symptoms may include headaches and cyanosis. It can cause dizziness and an increase in red blood cell Heinz bodies. Vertigo and an increase in sulfhemoglobin may occur. Drowsiness has been reported. The onset of symptoms may be delayed 2 to 4 hours or longer. Symptoms of exposure to a related compound include methemoglobinemia, skin sensitization, corneal damage, and liver and kidney damage.;ACUTE/CHRONIC HAZARDS: This compound is very toxic by ingestion, inhalation and skin contact. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. It is readily absorbed through the skin. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (NTP, 1992)

Hazards Summary · 1 件

May induce methemoglobinemia; [ICSC] A 42-day oral study of rats demonstrated effects suggestive of adverse effects on the hematopoietic system, liver, and kidney (LOAEL of 12 mg/kg/day); No parturition and decreased gestation index at 300 mg/kg/day (possible lethality in early fetal stages); [OECD SIDS] A strong skin, eye, and mucous membrane irritant; [HSDB] A skin and strong eye irritant; May induce methemoglobinemia; Harmful by ingestion; [Sigma-Aldrich MSDS] See o-Anisidine and p-Anisidine.

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. A water spray may also be used. (NTP, 1992)

Use water spray, dry powder, foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

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. Do NOT induce vomiting. 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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Safe StorageWell closed. Separated from food and feedstuffs and strong oxidants.
Fire Fighting Procedures · 2 件

Use dry chemical, carbon dioxide, or alcohol foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode. /Anisidines/

If material is involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Keep run-off water out of sewers and water sources. /Anisidines/

Storage Conditions · 1 件

Store in tightly closed containers in a cool, dark, well-ventilated area. Protect against sunlight and strong oxidizers. Metal containers involving the transfer of this chemical should be grounded and bonded. Where possible, automatically pump liquid from drums or other storage containers to process containers. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard. A regulated, marked area should be established where this chemical is handled, used, or stored ... /Anisidines/

毒性情報

Ecotoxicity Values · 5 件

LD50 Quail (Cotunix, sp.) oral 562 mg/kg

LC50; Species: Oryzias latipes (Orange-red killifish); Conditions: semi-static; Concentration: 620 mg/L (w/v) for 24 hr

LC50; Species: Oryzias latipes (Orange-red killifish); Conditions: semi-static; Concentration: 420 mg/L (w/v) for 48 hr

LC50; Species: Oryzias latipes (Orange-red killifish); Conditions: semi-static; Concentration: 240 mg/L (w/v) for 96 hr

For more Ecotoxicity Values (Complete) data for m-Anisidine (6 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 30(SRC), determined from a log Kow of 0.93(2) and a regression-derived equation(3), indicates that m-anisidine is expected to have very high mobility in soil(SRC). The pKa of m-anisidine is 4.24(4), indicating that this compound will partially exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of the neutral species of m-anisidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(6). m-Anisidine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.50X10-2 mm Hg at 25 °C(7). Biodegradation of m-anisidine varies depending on the conditions of the test and concns of the test sample and inoculum. It did not biodegrade during a Japanese MITI test(8), but degraded 60% to 100% after 30 days during another screening test using a variance of the Modified OECD test(9). Half-lives of 2 to 3 weeks in non-adapted sludge and <2 weeks in adapted sludge were reported(10).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 30(SRC), determined from a log Kow of 0.93(2) and a regression-derived equation(3), indicates that m-anisidine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected for the neutral species(4) based upon an estimated Henry's Law constant of 1.13X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). m-Anisidine degraded 37% in river water and 17% in seawater after 3 days during Cultivation Method screening test(8,9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), m-anisidine, which has a vapor pressure of 7.50X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase m-anisidine 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 1.9 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). m-Anisidine absorbs light at 285 nm(4); therefore, it will undergo direct photolysis by sunlight(SRC).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
Signs and Symptoms · 2 件

Blue lips, fingernails and skin. Dizziness. Headache. Nausea. Confusion. Convulsions. Unconsciousness.

See Inhalation.

Effluent ConcentrationsAnisidine (isomer not specified) has been identified in the effluent from chemical industries located in Kingsport, TN (Sept 1974), Morristown, TN (Sept 1974) and on the Upper Catawba River, TN (Aug 1974)(1).

法規制情報

Regulatory Information · 3 件

Chemical: Benzenamine, 3-methoxy-

Status: Active Update: 01-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20544

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

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, & 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 & environmental impact & energy requirements. Anisidine is produced, as an intermediate or a final product, by process units covered under this subpart. /Anisidine/

安全データ

F
8
wgk
1
tsca
TSCA listed
rtecs
BZ5408000
ridadr
UN 2431 6.1/PG 3
毒性
cyt-ham:ovr 160 mg/L EMMUEG 10(Suppl 10),1,87

化学と産業

薬理情報

Absorption, Distribution and ExcretionThe substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

用途と製造

Uses · 4 件

Used to make azo dyes; [Merck Index] Also used to make pharmaceuticals and textile-processing chemicals; [HSDB]

Anisidines are used in the manufacture of azo dyes, pharmaceuticals, textile-processing chemicals. /Anisidines/

Intermediate for dyestuffs.

4-Amino-6-methoxy-1,3-benzenedisulfonyl chloride is obtained by adding sodium chloride to m-anisidine and chlorosulfuric acid while cooling with ice and then heating.

Methods of Manufacturing · 2 件

3-Methoxyaniline may be prepared by methylation of 3-aminophenol under alkaline conditions, but it is more usual to protect the amino group and to methylate 3-acetylaminophenol, followed by hydrolysis.

Reduction of 3-nitrophenol and methylation to 3-nitroanisole followed by reduction gives m-anisidine.

General Manufacturing InformationBenzenamine, 3-methoxy-: ACTIVE
応用分野 · 3 件

用途有機合成原料。

使用m-Anisidine is a highly poisonous monosubstituted aniline used as corrosion inhibitorsfor aluminum, copper and other metals in acidic solutions.

一般的な説明M-anisidine appears as pale yellow oily liquid or dark red liquid. (NTP, 1992)

調製方法 · 1 件

純化方法o-Isomer impurity can be removed by steam distillation. Another possible impurity is the precursor 3-nitroanisole which can be removed as for the preceding o-isomer and fractionating using an efficient column. It is a yellow liquid. [Gilman & Kyle J Am Chem Soc 74 3027 1952, Bryson J Am Chem Soc 82 4858 1960, Kadaba & Massie J Org Chem 22 333 1957, Beilstein 13 IV 953.]

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関連反応

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