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Home > Encyclopedia > 2-Methoxy-5-nitroaniline

2-Methoxy-5-nitroaniline

2-Methoxy-5-nitroaniline structure

2-Methoxy-5-nitroaniline 

structure
  • CAS No:

    99-59-2

  • Formula:

    C7H8N2O3

  • Chemical Name:

    2-Methoxy-5-nitroaniline

  • Synonyms:

    Benzenamine,2-methoxy-5-nitro-;o-Anisidine,5-nitro-;2-Methoxy-5-nitrobenzenamine;1-Amino-2-methoxy-5-nitrobenzene;2-Methoxy-5-nitroaniline;5-Nitro-2-methoxyaniline;2-Amino-4-nitroanisole;5-Nitro-o-anisidine;3-Nitro-6-methoxyaniline;Azoamine Scarlet K;2-Amino-1-methoxy-4-nitrobenzene;1-Methoxy-2-amino-4-nitrobenzene;4-Nitro-2-aminoanisole;NSC 5510;(2-Methoxy-5-nitrophenyl)amine;2-(Methyloxy)-5-nitroaniline;52756-54-4

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

orange to brown powder 5-Nitro-o-anisidine is an orange-red crystalline compound.


5-nitro-o-anisidine appears as orange-red needles or orange powder. (NTP, 1992)


5-nitro-o-anisidine appears as orange-red needles or orange powder. (NTP, 1992)|2-methoxy-5-nitroaniline is a member of 4-nitroanisoles and a substituted aniline.

2-Methoxy-5-nitroaniline Basic Attributes

168.15

168.15

879620

202-770-5

THY70UTM0O

5510

2811

DTXSID0020943

ORANGE-RED NEEDLES FROM ALC, ETHER, WATER|Red needles from alcohol

2922299090

Characteristics

81.07000

1.69

5-nitro-o-anisidine appears as orange-red needles or orange powder. (NTP, 1992)

1.2068 g/cm3 @ Temp: 156 °C

118 °C

153-156 °C @ Press: 1.45 Torr

119℃

1.601

H2O: Slightly soluble . <0.01 g/100 mL at 19.5 ºC

Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.

pKa = 2.49 (conjugate acid)

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

5-NITRO-O-ANISIDINE is incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides and chloroformates (NTP, 1992).

Safety Information

I; II; III

6.1

NONH for all modes of transport

2

36/37/38-20/21/22

26-36-45-36/37

BZ7175000

Xi,Xn

Irritant

Stable, but may be moisture sensitive. Incompatible with water, acids, strong oxidizing agents, acid chlorides, acid anhydrides, chloroformates, liquid anisidine.

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.

Contact with strong oxidizers may cause fires and explosions. /o-Anisidine/|Liquid anisidine will attack some forms of plastics, rubber, and coatings. /o-Anisidine/

Bioassay of 5-Nitro-o-anisidine for Possible Carcinogenicity (1978) Technical Rpt Series No. 78-1382 DHEW Pub No. (NIH) 78-1382, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014|National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 5-Nitro-o-anisidine (99-59-2) is delisted as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/append/appb.pdf]

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Warning|H315 (85.11%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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 a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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)|Wear butyl rubber gloves, plastic coveralls, and self-contained breathing apparatus. /o-Anisidine/|Respirator selection: 2.5 mg/cu m or less: Any dust and mist respirator, except single use. 5 mg/cu m or less: Any dust and mist respirator, except single use or quarter mask respirator. Any supplied air respirator or any self contained breathing apparatus. 25 mg/cu m or less: Any high efficiency particulate filter respirator with full facepiece. Any supplied air respirator with a full facepiece, helmet, or hood or any self contained breathing apparatus with full facepiece. 50 mg/cu m or less: A powered air purifying respirator with high efficiency particulate filter or a Type C supplied air respirator operated in pressure demand or other positive pressure or continuous flow mode. Greater than 50 mg/cu m or entry and escape from unknown concentrations: Self contained breathing apparatus with full facepiece operated in pressure demand or other positive pressure mode or a combination respirator which includes a Type C supplied air respirator with a full facepiece operated in pressure demand or other positive pressure or continuous flow mode and an auxiliary self contained breathing apparatus operated in pressure demand or other positive pressure mode. /o-Anisidine/|Employees should be provided with and required to use dust- and splash-proof safety goggles where solid or liquid anisidine or liquids containing anisidine may contact the eyes. /o-Anisidine/|If employee's clothing ... contaminated ... change /them/ ... . Clothing contaminated with anisidine should be placed into closed containers for storage until it can be discarded or until provision is made for removal of anisidine from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the anisidine, the person performing the operation should be informed of anisidine's hazardous properties. /o-Anisidine/

Extinguishant: Foam, carbon dioxide, dry chemical. /o-Anisidine/|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/

1. Ventilate area of spill or leak. 2. Collect spilled material in most convenient and safe manner for reclamation or for disposal. Liquids containing anisidine should be absorbed in vermiculite, dry sand, earth, or a similar material. Large quantities may be reclaimed; however, if this is not practical, dissolve in flammable solvent (such as alcohol) and atomize in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device. /o-Anisidine/|Cover with the 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton, stuffed with ruffled paper. Burn in an open furnace with the utmost care or in the furnace with afterburner and scrubber. /o-Anisidine/

Where exposure of ... body to solid or liquid anisidine or liquids containing anisidine may occur, facilities for quick drenching of the body should be provided within the immediate work area ... . /o-Anisidine/|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/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Nitroanilines/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Nitroanilines/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Nitroanilines/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Nitroanilines/|For more DOT Emergency Guidelines (Complete) data for 5-NITRO-O-ANISIDINE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Toxicity

LD50 Rat oral 2250 mg/kg|LD50 Mouse oral 1060 mg/kg

A bioassay of 5-nitro-o-anisidine for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. /The cmpd/ was administered in the feed, at either of two concentrations, to groups of 50 male and 50 female animals of each species. The dietary concentrations used ... for low and high dose rats were 0.4 and 0.8%, respectively. Dose A and B mice were fed dietary concentrations of 0.8 and 1.6% when initially placed on test, but after wk 15 the concn fed to dose B mice was reduced to 0.4%. After a 78 wk period of chemical administration, observation of rats continued for up to an additional 28 wk and observation of mice continued for up to an additional 19 wk. For each species, 50 animals of each sex were placed on test as controls for the group receiving the higher concn and 49-50 animals of each sex were placed on test as controls for the group receiving the lower concn. ... Under the conditions of this bioassay, dietary administration of 5-nitro-o-anisidine was carcinogenic in Fischer 344 rats, causing tumors of the integumentary system in males and females and of the clitoral gland in females. The cmpd was carcinogenic to female B6C3F1 mice, causing hepatocellular carcinomas. Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Positive; Male Mice: Equivocal; Female Mice: Positive.

5-Nitro-o-anisidine's production and use in the production of dyes(1) may result in its release to the environment through various waste streams(SRC). 5-Nitro-o-anisidine may be released to the environment in wastewater(2).

TERRESTRIAL FATE: The amino group of 5-nitro-o-anisidine may bind covalently with active sites in soil which will result in low mobility(1). Volatilization of 5-nitro-o-anisidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 5-Nitro-o-anisidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-4 mm Hg(3), determined from a fragment constant method(3). No biodegradation data were found for 5-nitro-o-anisidine(SRC).|AQUATIC FATE: The amino group of 5-nitro-o-anisidine may bind covalently with active sites in soil which will result in low mobility in suspended solids and sediments(1). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 1.3X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF of 2.7(SRC), from its log Kow of 1.5(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low (SRC). No biodegradation data were found for 5-nitro-o-anisidine(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5-nitro-o-anisidine, which has an estimated vapor pressure of 3.2X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor. Vapor-phase 5-nitro-o-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 12 hours(SRC), calculated from its rate constant of 3.3X10-11 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 5-nitro-o-anisidine with photochemically-produced hydroxyl radicals has been estimated as 3.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). 5-Nitro-o-anisidine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Aromatic amines such as aniline have weak absorption bands that extend beyond 290 nm(4), therefore p-anisidine may be susceptible to direct photolysis, but the kinetics of this reaction are unknown. Aniline has been shown to undergo indirect photolysis in natural waters containing humic acids(5), therefore it is expected that p-anisidine may also undergo indirect photolysis in natural water.

An estimated BCF of 2.7 was calculated for 5-nitro-o-anisidine(SRC), using a log Kow of 1.5(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 5-nitro-o-anisidine is estimated as 150(SRC), using a log Kow of 1.47(2) and a regression-derived equation(3). According to a classification scheme(4), this estimated Koc value suggests that 5-nitro-o-anisidine is expected to have high mobility in soil. Aromatic amines, however, become strongly and irreversibly bound to humic materials when added to soil(5,6). This binding results from formation of covalent bonds between soil humus and the amine group of the aniline(5). As a result, 5-nitro-o-anisidine is expected to be relatively immobile in some soils and to be strongly bound to humic material found in suspended solids and sediments in water(SRC).

The Henry's Law constant for 5-nitro-o-anisidine is estimated as 1.3X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 5-nitro-o-anisidine is expected to be essentially nonvolatile from water surfaces(2). 5-Nitro-o-anisidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-4 mm Hg(3), determined from a fragment constant method(3).

Occupational exposure to 5-nitro-o-anisidine may occur through inhalation and dermal contact with this compound at workplaces where 5-nitro-o-anisidine is produced or used(1).

Drug Information

SYMPTOMS: Symptoms of exposure to this compound may include headaches, dizziness, cyanosis, and red blood cell Heinz bodies. Symptoms of exposure to related compounds includes methemoglobinemia, skin sensitization, irritation, corneal damage, and kidney and liver damage. ACUTE/CHRONIC HAZARDS: This compound is harmful if ingested, inhaled or absorbed through the skin. It is a positive animal carcinogen. 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. 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)

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/|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-methoxy-5-nitroaniline

2-Methoxy-5-nitroaniline Use and Manufacturing

Methods of Manufacturing

It is derived from 2, 4-dinitrochlorobenzene by methoxylation and reduction. 1. Methoxylation Add molten 2, 4-dinitrochlorobenzene into the reaction pot, and then add methanol. Heat to about 40℃, add 30% sodium hydroxide solution quickly and slowly within 4h, and control the temperature at 58-60℃. The end of the reaction is when the phenolphthalein test paper turns orange-red to the material liquid, and 2, 4-dinitroanisole is obtained with a yield of 95%. 2. Reduction Cool the above-mentioned methoxylation product to 30°C, and add 18% sodium disulfide solution quickly and then slowly within 4h, and the reaction temperature will gradually rise from 30°C to 50°C. After adding, keep it at 50-55℃ for half an hour. After the reaction is completed, it is cooled to 20°C, filtered under pressure, washed, and dried to obtain 2-methoxy-5-nitroaniline. The yield was 76%.

Uses

As an intermediate for dyes, pigments and organic synthesis

Production

(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Benzenamine, 2-methoxy-5-nitro-: ACTIVE

5-Nitro-o-anisidine can be gas chromatographed as determined by EPA Athens Environmental Research Laboratory or S-Cubed, Alexandria Va.|OSW Method 8270B. Determination Semivolatile Organic compounds by Gas Chromatography/Mass Spectrometry (GC/MS): Capillary Column Technique. Detection limit - 10.000 ug/l.|OSW Method 8270C. Semivolatile Organic Compounds by Gas Chromatography/ Mass Spectrometry (GC/MS): Capillary Column Technique.|SFSAS method SFSAS 29. Extraction and Analysis of Organics in Biological Tissue. Detection limit = 2.000 mg/kg.

Computed Properties

Molecular Weight:168.15
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:168.05349212
Monoisotopic Mass:168.05349212
Topological Polar Surface Area:81.1
Heavy Atom Count:12
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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