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Home > Encyclopedia > 3-Methoxyaniline

3-Methoxyaniline

3-Methoxyaniline structure

3-Methoxyaniline 

structure
  • CAS No:

    536-90-3

  • Formula:

    C7H9NO

  • Chemical Name:

    3-Methoxyaniline

  • Synonyms:

    Benzenamine,3-methoxy-;m-Anisidine;3-Methoxybenzenamine;3-Aminoanisole;m-Anisylamine;3-Methoxyaniline;m-Aminoanisole;1-Amino-3-methoxybenzene;m-Aminomethoxybenzene;3-Methoxyphenylamine;m-Methoxyaniline;NSC 7631;1-Methoxy-3-aminobenzene;3-(Methyloxy)aniline;918666-97-4

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Light yellow liquid. Anisidine exists as ortho-, meta-, and paraisomers. They have characteristic amine (fishy) odors.


M-anisidine appears as pale yellow oily liquid or dark red liquid. (NTP, 1992)|PALE YELLOW OILY LIQUID.


M-anisidine appears as pale yellow oily liquid or dark red liquid. (NTP, 1992)

3-Methoxyaniline Basic Attributes

123.15

123.15

386119

208-651-4

JXA144KX2I

0375

7631

2431

DTXSID8024529

Pale yellow, oily liquid

29222200

Characteristics

35.2

0.93

Clear yellow to brown Liquid

1.1 g/cm3

<0 °C

251 °C

>230 °F

1.555

H2O: <0.1 g/100 mL at 19 ºC

2-8°C

Vapour pressure, Pa at 25°C: 0.31

Oral-quail LD50: 562 mg/kg; Oral-Wild bird LD50: 562 mg/kg

Combustible in case of open flame; burning produces toxic nitrogen oxide fumes

Henry's Law constant = 1.13X10-7 atm-cu m/mole at 25 °C (est)

pKa = 4.24 (conjugate acid)

Remains fluid even at -10 °C; BP = 81-86 °C at 2 mm Hg|Hydroxyl radical reaction rate constant = 2.01X10-10 cu cm/molec-sec at 25 °C (est)

This chemical may be sensitive to prolonged exposure to air and light. Insoluble in water.

Ethers

M-ANISIDINE is incompatible with strong oxidizers. It is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. (NTP, 1992)

515 °C

Safety Information

III

6.1

UN 2431 6.1/PG 3

1

22-36/37/38-50/53-51/53-33-26/27/28

26-60-61-45-36/37-28B

BZ5408000

Xn,N,T+

The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

Stable under normal temperatures and pressures.

P261-P273-P305 + P351 + P338-P501

H302-H315-H319-H335-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Dissolve in combustible solvent (alcohols, benzene, etc.) and spray solution into furnace equipped with afterburner and scrubber or burn spill residue on sand and soda ash absorbent in a furnace. /Anisidines/

Materials to avoid: acids, acid chlorides, acid anhydrides, chloroformates, strong oxidizing agents|Incompatible with strong oxidizers, with risk of fire or explosions. Attacks some coatings and some forms of plastic and rubber. /Anisidines/

Organization for Economic Cooperation and Development; Screening Information Data Set for m-Anisidine, 536-90-3. This OECD Initial Assessment of HPV Chemicals is part of a series of OECD SIDS documents published by UNEP Chemicals to facilitate the access to information needed for health and environmental risk assessments of chemicals.[Available from, as of April 28, 2010: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html]

This chemical is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302 (98.52%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 135 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P260, P261, P264, P270, P272, P280, P302+P352, P309+P311, P314, P321, P333+P313, P363, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Face shield and safety glasses. Handle with gloves. Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Combustible

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/

Spill handling: Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area of spill or leak. Cover with sand and soda ash (9:1). After mixing, collect material in the most convenient and safe manner and deposit in sealed containers. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. It may be necessary to contain and dispose of this chemical as a hazardous waste. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. /Anisidines/|Collect leaking liquid in sealable containers. Do NOT let this chemical enter the environment.|Environmental considerations - land spill: Dig a pit, pond, lagoon, holding area to contain fluid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder or commercial respondents. /Anisidines/|Environmental considerations - water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Anisidines/|Environmental considerations - air spill: Apply water spray or mist to knock down vapors. /Anisidines/

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personal hazard. /Anisidines/|Personnel protection: Keep upwind. Avoid breathing vapors or dusts ... Do not handle broken packages unless wearing appropriate personal protective equipment. Avoid bodily contact with the material. /Anisidines/|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

Very irritating to skin, eyes, and mucous membranes. /Anisidines/

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.

Well closed. Separated from food and feedstuffs and strong oxidants.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.

NO open flames.

PREVENT GENERATION OF MISTS! STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

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/

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Anisidine (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).

m-Anisidine was detected in Latakia tobacco steam-distilled with sodium hydroxide and treated with hydrochloric acid(1).

Toxicity

moderately toxic

LD50 Rat male and female oral 526 mg/kg

Salmonella genotoxicity study for m-Anisidine, Salmonella typhimurium strains TA98, TA100, TA1535, TA1537, with and without metabolic activation (10% metabolic activation enzymes and cofactors from Aroclor 1254-induced male Sprague-Dawley rats or Syrian hamster liver). Results: negative|Salmonella genotoxicity study for m-Anisidine, Salmonella typhimurium strains TA98, TA100, TA1535, with and without metabolic activation (metabolic activation enzymes and cofactors from Aroclor 1254-induced male Sprague-Dawley rats (30%) or Syrian hamster (5, 10, or 30%) liver). Results: weak positive|Salmonella genotoxicity study for m-Anisidine, Salmonella typhimurium strains TA98, TA100, TA1535, TA1538, with and without metabolic activation (5%, 10%, or 30% metabolic activation enzymes and cofactors from Aroclor 1254-induced male Sprague-Dawley rats or Syrian hamster liver). Results: positive|Sister Chromatid Exchange study for m-Anisidine, with and without metabolic activation (induced rat liver S9). Results: positive (positive without metabolic activation, questionable without)|Chromosome abberation study for m-Anisidine, with and without metabolic activation (induced rat liver S9). Results: negative (with metabolic activation), positive (without metabolic activation)

m-Anisidine's production and use in the synthesis of 4-amino-6-methoxy-1,3-benzenedisulfonyl chloride(1) may result in its release to the environment through various waste streams(SRC).

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).

The rate constant for the vapor-phase reaction of m-anisidine with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). m-Anisidine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). m-Anisidine absorbs light at 285 nm(3); therefore, it will undergo direct photolysis by sunlight(SRC).

An estimated BCF of 3.2 was calculated for m-anisidine(SRC), using a log Kow of 0.93(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of m-anisidine is estimated as 30(SRC), using a log Kow of 0.93(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that m-anisidine is expected to have very high mobility in soil. 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).

The Henry's Law constant for m-anisidine is estimated as 1.1X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that m-anisidine is expected to be essentially nonvolatile from water surfaces(2). m-Anisidine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.50X10-2 mm Hg(3).

Occupational exposure to m-anisidine may occur through dermal contact with this compound at workplaces where m-anisidine is produced or used. (SRC)

Drug Information

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

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)

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)


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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

/SIGNS AND SYMPTOMS/ Short term exposure: ... can be absorbed through the skin, eyes, or mucous membranes, thereby increasing exposure. Contact with anisidines can irritate the eyes, skin, and respiratory tract, can cause a burning sensation and skin rash. Exposure can interfere with the blood's ability to carry hemoglobin (methemaglobinemia). This can cause headache, dizziness, cyanosis of the skin and lips. Higher levels can cause difficult breathing, collapse, and death. Long term exposure: Related aromatic amines are carcinogens ... Repeated exposure to these isomers may cause anemia, skin allergy, lung irritation, and bronchitis; nerve and kidney damage. /Anisidines/

3-anisidine

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

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

3-Methoxyaniline Use and Manufacturing

Methods of Manufacturing

It is derived from the reduction of m-nitrophenol on the hydroxyl group after methylation.

Uses

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

Benzenamine, 3-methoxy-: ACTIVE

Computed Properties

Molecular Weight:123.15
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:123.068413911
Monoisotopic Mass:123.068413911
Topological Polar Surface Area:35.2
Heavy Atom Count:9
Complexity:85
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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