4-Fluoroaniline

111.12

111.12

742030

206-735-5

60HI1G076Z

579

2941

DTXSID9022027

Liquid|Pale yellow liquid

29214210

26

1.15

Clear pale yellow to red-brown Oily Liquid

1.1725 g/cm³ @ Temp: 20 °C

-1.9 °C

188 °C

165 °F

1.548

H2O: 33 g/L (20 ºC)

2-8°C

0.75 mm Hg (1 hectoPa) at 20 deg C

Oral-Rat LD50: 417 mg/kg; Oral-Quail LD50: 100 mg/kg

Open flame is flammable; high heat decomposes toxic fluoride and nitrogen oxide gas

Henry's Law constant = 6.1X10-6 atm-cu m/mol at 25 °C (est)

pKa = 4.65 at 25 °C (conjugate acid)

UV: 8-41 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /2-Fluoroaniline/

Insoluble in water.

Aryl Halides

Special Hazards of Combustion Products: Irritating and toxic hydrogen fluoride and oxides of nitrogen may form in fires. (USCG, 1999).

780.4 kcal/mol

III

6.1

UN 2941 6.1/PG 3

1

22-34-36/38-33-23/24/25

26-36/37/39-45-37/39-28

BY1575000

C,T,Xi,Xn

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

Toxic/Irritant

Stable. Incompatible with acids, oxidizing agents.

P280-P305 + P351 + P338-P310

H302-H314

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.

Special Hazards of Combustion Products: Irritating and toxic hydrogen fluoride and oxides of nitrogen may form in fires. (USCG, 1999)

|Danger|H302 (98.31%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P314, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P405, and P501|Aggregated GHS information provided by 179 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H227: Combustible liquid [Warning Flammable liquids]|P210, P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P370+P378, P403+P235, 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)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Rubber gloves; chemical goggles; protective clothing; dust respirator. (USCG, 1999)|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose 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). Hand protection: Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. Eye protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin and body protection Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

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 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.

/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. /Fluoroanilines/|/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. /Fluoroanilines/|/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. /Fluoroanilines/|/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. /Fluoroanilines/|For more DOT Emergency Guidelines (Complete) data for 4-FLUOROANILINE (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.

A severe skin and eye irritant.

highly

LD50 Rat oral 417 mg/kg

/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.

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).

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).

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).

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).

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).

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).

Occupational exposure to 4-fluoroaniline may occur through inhalation and dermal contact with this compound at workplaces where 4-fluoroaniline is produced or used. (SRC)

The in vitro hydroxylation-defluorination of p-fluoroaniline was carried out by liver microsomes from the rabbit, rat, sheep, cow, pig, man and pigeon, but not by microsomes prepared from trout.|p-Fluoroaniline is defluorinated notably in vivo in rats, clearly evidenced by the increase in urinary fluoride.|Possible methods for monitoring exposure to 2,4-difluoroaniline and 4-fluoroaniline were studied in rats. Wistar rats were given 1.0, 0.25, and 0.13 millimoles per 0.1 kilogram 2,4-difluoroaniline or 4-fluoroaniline. Blood samples were taken at 1 hr before and 1, 2, 4, 6, 8, and 24 hr after dosing. Methemoglobin was calculated from absorbance at 630 nm before and after adding potassium cyanide to lysed blood. Urinary metabolites were isolated as cetylpyridinium salts from rats similarily dosed with 4-fluoroaniline and 2,4,-difluoroaniline. 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 cmpd was rapid and only low concentrations were detected the second day after dosing. About 39% of 4-fluoroanilne and 13% of 2,4-difluoroaniline were accounted by these metabolites.|The regioselectivity and metabolism of monofluoroanilines were studied in-vivo and in-vitro. Male Wistar-rats were administered 0 or 50 mg/kg 2-fluoroaniline, 3-fluoroaniline, or 4-fluoroaniline orally. Urine samples were collected 24 hours later and analyzed for metabolites by fluorine-19 nuclear magnetic resonance spectroscopy. Liver microsomes prepared from male Wistar-rats that had been pretreated with the cytochrome-P-450 (P450) inducers were fortified with P450 and incubated with 0 or 10 millimolar 2-fluoroaniline, 3-fluoroaniline, or 4-fluoroaniline for 10 minutes. The incubates were analyzed for metabolites. Frontier electron densities of occupied and unoccupied orbitals of 2-fluoroaniline, 3-fluoroaniline, and 4-fluoroaniline were calculated by a computerized semiempirical molecular orbital technique. 3-Fluoro-4-acetamidophenylsulfate, 3-fluoro-4-aminophenylsulfate, and 3-fluoro-4-acetamidophenylglucuronide were the major 2-fluoroaniline urinary metabolites. 2-Fluoro-4-acetamidophenylsulfate, 4-fluoro-2-aminophenylsulfate, 2-fluoro-4-aminophenylsulfate, and the fluoride-ion (F-) were the major metabolites of 3-fluoroaniline. 5-Fluoro-2-aminophenylsulfate and fluoride-ion were the major metabolites of 4-fluoroaniline. In-vitro, 3-fluoro-4-aminophenol was the major 2-fluoroaniline metabolite. 3-Fluoroaniline was converted primarily to 4-aminophenol and 4-fluoro-2-aminophenol. 4-Fluoroaniline was converted primarily to 5-fluoro-2-aminophenol and F-. In microsomes from rats pretreated with the P450 inducers, 3-fluoroaniline underwent hydroxylation primarily in the para position, the extent of hydroxylation being similar for all pretreatment conditions. Ortho hydroxylation at the C6 position occurred under all pretreatment conditions but to a much smaller extent. Ortho hydroxylation at the C2 position occurred only in microsomes from rats pretreated with 3MC and isosafrole. Frontier electron densities in the highest occupied molecular orbital (HOMO) and the orbital just below it (HOMO-1) were highest in the C4 position followed by the C6 and C2 positions. /The investigators/ conclude that the regioselectivity in the hydroxylation of 3-fluoroaniline can be explained by higher electron densities in the HOMO and HOMO-1 orbitals of the C4 and C6 carbons and the low density at the C2 position. P450 catalyzed hydroxylation of monofluoroanilines apparently involves electrophilic attack of a charged iron/oxygen species derived from P450 on a specific carbon atom of the aromatic ring.|For more Metabolism/Metabolites (Complete) data for 4-FLUOROANILINE (6 total), please visit the HSDB record page.

Inhalation or ingestion causes bluish tint to fingernails, lips and ears indicative of cyanosis; headache, drowsiness, and nausea, followed by unconsciousness. Liquid can be absorbed through skin and cause similar symptoms. Contact with eyes causes irritation. (USCG, 1999)

INHALATION: Remove victim from exposure immediately; if needed, administer oxygen; refer to physician. EYES: Flush with water for at least 15 min. SKIN: Remove victim from exposure immediately; remove contaminated clothing; wash contacted area with copious amounts of water and soap; if needed, administer oxygen; refer to physician. INGESTION: Induce vomiting; get medical attention. (USCG, 1999)

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/|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/|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/

4-fluoroaniline

Benzenamine, 4-fluoro-: ACTIVE

Group-specific colorimetric method and substance-specific gas-chromatographic method of aromatic amines and derivatives in surface waters.|Aniline derivatives in wastewater determined by gas and liquid chromatography.|Aromatic and aliphatic amines were separated by TLC; 20 solvent systems were examined.|Two complementary methods for analysis of primary aromatic amines in a mixture such as air were reported: A TLC method for rapid screening with a low-nanogram detection level, and a high-performance liquid chromatographic (HPLC) method with a picogram detection capability.

Environmental transformation -> Pesticide transformation products (metabolite, successor)

4-fluoroaniline is a known environmental transformation product of picolinafen.|4-fluoroanaline is a known environmental transformation product of Picolinafen.