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Home > Encyclopedia > 4-Methoxy-2-methylaniline

4-Methoxy-2-methylaniline

4-Methoxy-2-methylaniline structure

4-Methoxy-2-methylaniline 

structure
  • CAS No:

    102-50-1

  • Formula:

    C8H11NO

  • Chemical Name:

    4-Methoxy-2-methylaniline

  • Synonyms:

    Benzenamine,4-methoxy-2-methyl-;p-Anisidine,2-methyl-;4-Methoxy-2-methylbenzenamine;4-Methoxy-2-methylaniline;2-Methyl-4-methoxyaniline;2-Methyl-p-anisidine;2-Amino-5-methoxytoluene;m-Cresidine;2-Methyl-4-anisidine;2-Methyl-4-methoxybenzenamine;NSC 66563;4-Methoxy-o-toluidine;2-Methyl-4-(methyloxy)aniline;[2-Methyl-4-(methyloxy)phenyl]amine;3-Methyl-4-aminophenol methyl ether

  • Categories:

    Organic Chemistry  >  Amides

Description

brick red crystals or liquidCrystals or brick red liquid.


Crystals or brick red liquid. (NTP, 1992)


Crystals or brick red liquid. (NTP, 1992)|Meta-Cresidine is a member of methoxybenzenes.

4-Methoxy-2-methylaniline Basic Attributes

137.18

137.18

774727

203-036-7

F0E8Y56GUK

66563

2810

DTXSID2020349

Crystals from ligroin

29222990

Characteristics

35.2

1.2

Crystals or brick red liquid. (NTP, 1992)

1.065 g/cm3 @ Temp: 25 °C

29.5 °C

248.5 °C

>230 °F

n 20/D 1.565(lit.)

H2O: insoluble , <0.1 g/100 mL at 21.5 ºC;Very soluble in ethanol

Refrigerator

0.023mmHg at 25°C

Sensitive to prolonged exposure to air and light. Insoluble in water.

Amines, Aromatic

M-CRESIDINE neutralizes acids in weakly exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. Reacts with oxidizing agents (NTP, 1992).

Safety Information

III

6.1

2810

3

36/37/38-40-45

26-36/37/39-53-45

BZ6730000

Xi,Xn,T

Stable. May be light or air-sensitive. Combustible. Incompatible with acids, strong oxidizing agents.

P261-P305 + P351 + P338

H315-H319-H335

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

This chemical is probably combustible. (NTP, 1992)

|Warning|H315 (89.36%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound should be controlled with a dry chemical carbon dioxide or Halon extinguisher. (NTP, 1992)

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)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxicity

m-Cresidine, an aromatic amine and dyestuff intermediate, was selected for bioassay by the National Cancer Institute because of the high incidence of bladder cancer associated with exposure to aromatic amines and several other classes of chemicals among workers in the dye manufacturing industry. A bioassay of technical-grade m-cresidine for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. m-Cresidine in corn oil was administered by gavage five days a weeks at either of two dosages, to groups of 50 male and 49 or 50 female animals of each species. The dosages used in the chronic bioassay for low and high dose rats were 0.08 and 0.16 gm/kg/day, respectively. The time-weighted average dosages used for low and high dose mice were 0.06 and 0.11 gm/kg/day, respectively. After a 77-week dosing period observation of rats continued for an additional 32 to 33 weeks. After a 53-week dosing period, observation of mice continued for an additional observation period of up to 41 weeks. For each species, 50 animals of each sex were placed on test as untreated controls and 25 animals of each sex were placed on test as vehicle controls. The urinary bladder and the kidney were the target organs of m-cresidine toxicity in male and female rats. Papillary transitional-cell carcinomas of the urinary bladder occurred in 0/45 low dose males, 5/44 (11 percent) high dose males, 1/46 (2 percent) low dose females, and 2/44 (5 percent) high dose females but did not occur in any untreated control or vehicle control rats. Although the incidences in each dosed rat group were not statistically significant when compared to vehicle controls, comparison with historical controls indicates that these bladder carcinomas are rare and are, therefore, considered to be compound-related in both sexes. Among mice, dose-related nonneoplastic lesions were observed at higher incidences for males than females in the kidneys, spleen and thymus. Dose-related toxic effects were also observed in testes of male mice. No neoplasms occurred in male mice at statistically significant incidences. Under the conditions of this bioassay, m-cresidine was carcinogenic to Fischer 344 rats, causing papillary transitional-cell carcinomas of the urinary bladder in both sexes. No convincing evidence was provided for carcinogenicity in female B6C3F1 mice. Poor survival of male B6C3F1 mice receiving m-cresidine precluded evaluation of the possible carcinogenicity of the compound in these animals.

m-Cresidine's former production and use as a dye intermediate(1) may have resulted in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from a log Kow of 1.23(2) and a regression-derived equation(3), indicates that m-cresidine is expected to have high mobility in soil(SRC). However, anilines (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). Volatilization of m-cresidine from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(6). m-Cresidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.025 mm Hg(SRC), determined from a fragment constant method(7). Based on data for p-cresidine, a structural analog; m-cresidine is not expected to readily biodegrade in soil(SRC). For example, p-cresidine, present at 100 mg/l, reached 0.7% of its theoretical BOD in 2 weeks, using an activated sludge inoculum at 30 mg/l, and the Japanese MITI test(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from a log Kow of 1.23(2) and a regression-derived equation(3), indicates that m-cresidine is expected to adsorb slightly to suspended solids and sediment(SRC). Volatilization from water surfaces may occur (3) based upon an estimated Henry's Law constant of 1.2X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 and 169 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 2(SRC), from an estimated log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on data for p-cresidine, a structural analog; m-cresidine is not expected to readily biodegrade in aqueous environments(SRC). For example, p-cresidine, present at 100 mg/l, reached 0.7% of its theoretical BOD in 2 weeks, using an activated sludge inoculum at 30 mg/l, and the Japanese MITI test(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), m-cresidine, which has an estimated vapor pressure of 0.025 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase m-cresidine 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 3.3 hours(SRC), calculated from its rate constant of 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of m-cresidine with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). m-Cresidine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

An estimated BCF of 2 was calculated for m-cresidine(SRC), using a log Kow of 1.23(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-cresidine is estimated as 110(SRC), using a log Kow of 1.23(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that m-cresidine is expected to have high mobility in soil(SRC). However, anilines (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 Henry's Law constant for m-cresidine is estimated as 1.2X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that m-cresidine may volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 15 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 169 days(SRC). m-Cresidine's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). m-Cresidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.025 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to m-cresidine may have occurred through dermal contact with this compound at workplaces where m-cresidine was produced or used. (SRC)

Drug Information

ACUTE/CHRONIC HAZARDS: This compound is a local irritant. When heated to decomposition it emits toxic fumes of NOx. This compound is an experimental animal carcinogen. (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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . 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 normal saline 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 patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

2-cresidine

4-Methoxy-2-methylaniline Use and Manufacturing

Methods of Manufacturing

General procedure: Nitro aromatic (1.0 mmol), B2(OH)4 (5.0 equiv, 5.0 mmol), and H2O (3.0 mL) were added in a10 mL tube. The reaction mixture was stirred at 80 °C for 8 h. When the reaction was completemonitored by TLC, the mixture was cooled to room temperature, extracted with ethyl acetate (3 ×20 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel columnchromatography.General procedure: Nitrobenzene (0.6mmol), 5wtpercent Pd/C (0.5mmol percent, 0.003mmol), H2O (10 equiv, 6.0mmol), B2(OH)4 (3.3 equiv, 2.0mmol), and CH3CN (1.0mL) were added in a 10mL tube. The reaction mixture was stirred at 50°C for 24h. When the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (5mL) was added, and extracted with EtOAc (3×5mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give aniline 2a (55mg, 99percent).EXAMPLE 1396-((l-(2-(3-Fluoro-6-methoxy-8-methylquinolin-4-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylamino)methyl)-2H-pyrido[3, 2-b][l, 4]oxazin-3(4H)-oneStep 14-Methoxy-2-methylanilineA solution of 4-methoxy-2-methyl-l -nitrobenzene (20.0 g) in methanol (150 mL) was added Pd/C (1.0 g), then stirred under H

Uses

Used as medicine and dye intermediate

Benzenamine, 4-methoxy-2-methyl-: ACTIVE

Computed Properties

Molecular Weight:137.18
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:137.084063974
Monoisotopic Mass:137.084063974
Topological Polar Surface Area:35.2
Heavy Atom Count:10
Complexity:105
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

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