4-フルオロアニリン

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

INHALATION: Remove victim from exposure immediately; if needed, administer oxygen; refer to physician.

General First Aid:

Suitable extinguishing media: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Special protective equipment for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

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.

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.

Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

1.8 [mg/m3]

20 [mg/m3]

120 [mg/m3]

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 113(SRC), determined from a structure estimation method(2), indicates that 4-fluoroaniline is expected to have high mobility in soil(SRC). The pKa of 4-fluoroaniline is 4.65(3), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. However, anilines 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). 4-Fluoroaniline has been observed to bind rapidly with soil in herbicide degradation studies(6). Volatilization of 4-fluoroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 4-Fluoroaniline is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.75 mm Hg at 20 °C(7). Limited biodegradation data indicate that 4-fluoroaniline is biodegradable(8,9), but its rate and relative environmental importance is not certain(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 113(SRC), determined from a structure estimation method(2), indicates that 4-fluoroaniline is expected to adsorb to suspended solids and sediment(SRC). The pKa of 4-fluoroaniline is 4.65(3), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. Anilines may bind strongly to humus or organic matter due to the high reactivity of the aromatic amino group(4,5), suggesting some adsorption to suspended solids and sediment may occur(SRC). Volatilization from water surfaces is expected(6) based upon an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(6), volatilization half-lives for a model river and model lake are 6.4 and 50 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow of 1.15(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Fluoroaniline absorbs at wavelengths >290 nm(8) and, therefore, may be susceptible to direct photolysis(SRC). Aromatic amines are susceptible to photosensitized degradation in natural waters exposed to sunlight due to reaction with OH and RO2 radicals(9); therefore, indirect photolysis may have some environmental importance in natural water(SRC). 4-Fluoroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-fluoroaniline, which has a vapor pressure of 0.75 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-fluoroaniline 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 11 hours(SRC), calculated from its rate constant of 3.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 4-Fluoroaniline absorbs at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

/OTHER TERRESTRIAL SPECIES/ ... In the present study, earthworms (Eisenia veneta) were exposed to three different model xenobiotics by a standard filter paper contact test, and toxicant-induced biochemical changes were then investigated by characterizing the changes in endogenous metabolites visible in 600-MHz 1H NMR spectra of tissue extracts. The NMR spectral intensities were converted to discrete numerical values and tabulated in order to provide data matrices suitable for multivariate analysis. Principal component analysis showed that changes had occurred in the biochemical profiles relative to the undosed controls. ... The 4-fluoroaniline-treated worms showed a decrease in maltose concentrations, and 3,5-difluoroaniline exerted the same effect as 2-fluoro-4-methylaniline but to a lesser extent. These changes could potentially be used as novel biomarkers of xenobiotic toxicity and could be used to determine the mechanism of action of other toxic chemicals.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4-fluoroaniline can be estimated to be 113(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-fluoroaniline is expected to have high mobility in soil. The pKa of 4-fluoroaniline is 4.65(4), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. 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). In aerobic soil degradation studies, 4-fluoroaniline that was formed as a principal metabolite of herbicide degradation, was observed to bind rapidly to soil(6).

4-Fluoroaniline's production and use as an intermediate in the manufacture of herbicides(1) may result in its release to the environment through various waste streams(SRC). 4-Fluoroaniline has been identified as a principal soil degradation product of the herbicides Sniper and Paragon (active ingredient)(2) which will result in its direct release to the environment(SRC).

AEROBIC: In biodegradation studies using Elbe River water and a testfilter methodology, 4-haloanilines (4-chloro and 4-bromo) had mean degradation rates of 0.67-0.70/hr (half-life of about 1 hour). The degradation rate in control samples was only 0.007-0.009/hr (half-life of 77-99 hours)(1); 4-fluoroaniline may have similar rates(SRC).

ANAEROBIC: In anaerobic biodegradation tests using an estuarine sediment from the Tsurumi River in Japan, 4-fluoroaniline had an observed degradation rate of 0.00328/day which corresponded to a half-life of 211.3 days(1).

PURE CULTURE: Purified enzymes of the soil fungus Geotrichum candidum biotransformed 500 ppm 4-fluoroaniline, yielding fluoroazobenzene as a metabolite(1). A strain of the soil bacterium Moraxella used 0.2 mm 4-fluoroaniline as a sole source of carbon and nitrogen(2).

An estimated BCF of 3 was calculated in fish for 4-fluoroaniline(SRC), using a log Kow of 1.15(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 4-fluoroaniline is estimated as 6.1X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-fluoroaniline is expected to 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 6.4 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 50 days(SRC). 4-Fluoroaniline's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 4-Fluoroaniline is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.75 mm Hg at 20 °C(3).

/LABORATORY ANIMALS: Neurotoxicity/ The potential for neurotoxicity after a single oral dose of four halogenated aniline derivatives, 4-bromoaniline, 4-chloroaniline, 4-fluoroaniline and 4-iodoaniline -- was given to rats was investigated at or near the lethal dosage level /500 mg/kg 4-bromoaniline, 300 mg/kg 4-chloroaniline, 600 mg/kg 4-fluoroaniline, 700 mg/kg 4-iodoaniline/. Hindlimb paralysis was found in the 4-bromoaniline, 4-chloroaniline and 4-fluoroaniline groups on clinical observation, with the maximum incidence of 100% in the 4-bromoaniline and 4-fluoroaniline groups and 66.7% in the 4-chloroaniline group. Detailed clinical observations with functional tests identified the following effects: reduced response of hindlimb extensor thrust, gait abnormality in the open field and decreased grip strength in the fore- or hindlimbs in the 4-bromoaniline, 4-chloroaniline and 4-fluoroaniline groups; decreased number of supported rearing episodes in the open field in the 4-bromoaniline and 4-chloroaniline groups; abnormal landing in the aerial righting reflex in the 4-bromoaniline and 4-fluoroaniline groups; and prolonged surface righting reflex in the 4-bromoaniline group. Spongy change in the white matter of the spinal cord and brainstem and nerve fibre degeneration in the peripheral nerves were found in all haloaniline-treated groups. The central and peripheral nervous systems were most severely affected in the 4-bromoaniline group and the lesions in the 4-iodoaniline group were limited in grade. This study demonstrates that a bolus dose of 4-haloanilines to rats induces a neurotoxicity similar in character to that evoked by the parent aniline. The decreasing order of neurotoxic potential appears to be 4-bromoaniline >> 4-fluoroaniline > or = 4-chloroaniline >> 4-iodoaniline when comparing at or near the lethal dosage level.

/GENOTOXICITY/ Several substituted alkyl- and haloanilines were tested for their ability to mutate Salmonella typhimurium and to damage the DNA of mammalian (Chinese hamster lung V79) cells. These results were correlated with their reported carcinogenicity. Of 9 suspected carcinogens, 4 were bacterial mutagens and 4 (of 7 tested) damaged DNA of V79 cells. The following compounds were weakly mutagenic (< 150 revertants/mumole): 4-fluoroaniline ... .

/BIOMONITORING/ Possible methods for monitoring exposure to 2,4-difluoroaniline and 4-fluoroaniline were studied in rats. Wistar-rats were given 1.0, 0.5, 0.25, and 0.13 millimoles per 0.1 kilogram 2,4-difluoroaniline or 4-fluoroaniline or 1.0 millimole per kilogram 4-chloroaniline as a positive control. Blood samples were taken at 1 hour before and 1, 2, 4, 6, 8, and 24 hours after dosing. Methemoglobin was calculated from absorbance at 630 nanometers before and after adding potassium-cyanide to lysed blood. Urinary metabolites were isolated as cetylpyridinium salts from rats similarly dosed with 4-fluoroaniline and 2,4-difluoroaniline. Metabolites were identified by nuclear magnetic resonance and elemental analysis. Neither test compound was as potent an inducer of methemoglobin as the positive control. At all doses of either compound methemoglobin increased rapidly and dropped quickly, returning to background values by 24 hours except at the highest doses. The dose response for each compound was approximately linear. The limit of detection was about 5 milligrams per 0.1 kilogram. Analysis of urinary metabolites confirmed that these were the O-sulfates of 2-amino-5-aminophenol and 2-amino-3,5-difluorophenol. The excretion of the urinary conjugated aminophenols after oral dosing with these compounds was rapid and only low concentrations were detected the second day after dosing. About 39 percent of 4-fluoroaniline and 13 percent of 2,4-difluoroaniline were accounted for by these metabolites. The authors conclude that either method could be used for human exposure monitoring. Methemoglobin determination is rapid and simple but not a very sensitive indicator. Urinary metabolite measurement is more sensitive but more complicated to perform.

The rate constant for the vapor-phase reaction of 4-fluoroaniline with photochemically-produced hydroxyl radicals has been estimated as 3.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Fluoroaniline absorbs at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Aromatic amines are susceptible to photosensitized degradation in natural waters exposed to sunlight due to reaction with OH and RO2 radicals(3); therefore, indirect photolysis may have some environmental importance in natural water(SRC). 4-Fluoroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4).

Used as an intermediate in the manufacture of herbicides, plant growth regulators, dyes, and para-Fluorophenol; [HSDB]

Intermediate in manufacture of herbicides and plant growth regulators.

Preparation of para-fluorophenol

4-Fluoroaniline is an intermediate for liquid crystal polymers

2023: 78,500 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4149]

All Other Basic Organic Chemical Manufacturing

Benzenamine, 4-fluoro-: ACTIVE