2-Methoxy-5-nitroaniline

log Kow= 1.47

1.47

1.2068 at 313 °F (NTP, 1992) - Denser than water; will sink

1.2068 @ 156 °C

ORANGE-RED NEEDLES FROM ALC, ETHER, WATER

Red needles from alcohol

less than 0.1 mg/mL at 67.1 °F (NTP, 1992)

Very sol in alcohol, acetone, benzene, acetic acid, ethyl acetate; soluble in ligroine

SLIGHTLY SOL IN PETROLEUM ETHER

In water, 115 mg/l @ 23 °C

244 °F (NTP, 1992)

118 °C

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

Orange-red to red solid; [HSDB] Orange crystalline powder; [MSDSonline]

Warning

H302 (12.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

Status: Cease Manufacture Update: 11-12-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/10119

Benzenamine, 2-methoxy-5-nitro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

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.

Harmful by inhalation, ingestion, and skin absorption; Potential health effects include methemoglobinemia, skin sensitization, and injury to the kidneys and liver; [CAMEO] An irritant; Effects in high-dose animal studies include abnormal liver function tests; [MSDSonline]

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]

/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.

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.

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/

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.

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.

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/

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.

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/

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 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=99-59-2]

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).

5-Nitro-ortho-anisidine

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 27: (1982) Some Aromatic Amines, Anthraquinones and Nitroso Compounds, and Inorganic Fluorides Used in Drinking-water and Dental Preparations

1987

1987

5-Nitro-o-anisidine

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 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).

Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Positive; Male Mice: Equivocal; Female Mice: Positive.

5-Nitro-ortho-anisidine induced reverse mutations in Salmonella typhimurium strain TA98 in the absence of metabolic activation.

No data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

5-Nitro-o-anisidine: delisted as reasonably anticipated to be a human carcinogen.

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.

Used to make dyes and pigments; Also used in azoic dye compositions for cotton, nylon, acetate, and silk; [HSDB]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

CHEM INT FOR DYES AND PIGMENTS (EG, CI PIGMENT RED 23); COMPONENT IN AZOIC DYE COMPOSITIONS FOR COTTON AND NYLON, ACETATE AND SILK.

Dye and pigment manufacture

(1977) 2.46X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 4.96X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

PARTIAL REDUCTION OF 2,4-DINITROANISOLE; NITRATION OF O-ANISIDINE; BY-PRODUCT IN MANUFACTURE OF 5-NITRO-2-AMINOANISOLE

Prepared either by partial reduction of 2,4-dinitroanisole with ammonium or sodium sulfide or by nitration of 2-methoxyaniline.