Phenyl-1-naphthylamine

219.28

219.28

2211174

201-983-0

5I112077IN

1113

2622

3077

DTXSID2025892

Prisms or needles from alcohol; leaflets from ligroin.|Tan to purple crushed solid or crystals.|White to yellowish crystals|In its pure form crystallizes into lemon yellow prisms or needles ... marketed in the form of brown to dark violet crystals or light brown to light violet granules

29214980

12

4.4

Pinkish to light brown Crystals or Flakes

1.2 g/cm³

61 °C

335 °C @ Press: 558 Torr

>200°C

1.702

H2O: insoluble

2-8°C

0.504 hPa (150 °C)

LD50 orally in Rabbit: > 2000 mg/kg

Amine-like

Henry's Law constant = 1.4X10-7 atm-cu m/mole @ 25 °C /Estimated/

pKa = 4.93 @ 25 °C

Decomposes on heating or burning, producing irritating or toxic fumes or gases. Conversion factor: 1 ppm = 9.114 mg/cu m @ 101.3 kPa and 20 °C.|Hydroxyl radical reaction rate constant = 3.5X10-10 cu cm/molec-sec @ 25 °C /Estimated/

May be sensitive to prolonged exposure to air. Insoluble in water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].

Amines, Phosphines, and Pyridines

N-PHENYL-1-NAPHTHYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

III

9

3077

2

22-36/37/38-50/53-43

26-36-61-37/39-29-60-36/37

QM4500000

Xn,N

Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

Stable. Incompatible with strong oxidizing agents, strong acids.

P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

International Programme on Chemical Safety's Concise International Chemical Assessment Documents. Number 9: N-Phenyl-1-naphthylamine (1998). Available from http://www.inchem.org/documents/cicads/cicads/cicad9.htm as of July 26, 2004.

Flash point data for this compound are not available. It is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302 (90.41%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P314, P321, P330, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 1632 companies from 42 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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 keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Powder, water spray, foam, carbon dioxide. ...In case of fire: keep drums, etc., cool by spraying with water. /from table/

Sweep spilled substance into sealable containers. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

AVOID ALL CONTACT!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield.

N-Phenyl-1-naphthylamine was identified, not quantified in wastewater samples being released into the Providence River, Massachusetts(1,2).

SEDIMENT: N-Phenyl-1-naphthylamine was identified, not quantified in sediment samples from Narragansett Bay, Massachusetts(1,2).

LD50 Rat oral 1625 mg/kg|LD50 Mouse oral 1231 mg/kg

/AQUATIC SPECIES/ Sublethal N-phenyl-1-naphthylamine concentrations of approximately 5.2 and 5.6 mg/L had teratogenic effects on embryos and larvae, respectively, of the clawed frog (Xenopus laevis). Concentrations above 6.2 mg/L were lethal (100% death of larvae within 24 hr) for both. ...For larvae of the leopard frog (Rana pipiens), a 48-hr LC100 of 5 mg/L was reported ...

N-Phenyl-1-naphthylamine's production and use as an antioxidant in various lubrication oils and as both a protective agent and antioxidant in rubber and rubber mixtures for various products, including tires(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a log Kow of 4.20(2) and a regression-derived equation(3), indicates that N-phenyl-1-naphthylamine is expected to have slight mobility in soil(SRC). The pKa of N-phenyl-1-naphthylamine is 4.93 at 25 °C(4) indicating that this compound will partially exist in the cation form in the environment(5). Volatilization of N-phenyl-1-naphthylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.13X10-5 mm Hg(6), and water solubility, 60 mg/L(7). N-Phenyl-1-naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(7). A 17% CO2 evolution when incubated in temperate soil after 11 days(8) indicates that N-phenyl-1-naphthylamine biodegradation in soil is not a major environmental fate process(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a log Kow of 4.20(2) and a regression-derived equation(3), indicates that N-phenyl-1-naphthylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.13X10-5 mm Hg(4), and water solubility, 60 mg/L(5). According to a classification scheme(6), a BCF range of 427 to 2,730(5), suggests bioconcentration in aquatic organisms is high to very high(SRC). Measured photochemical degradation half-lives in water of 8.4 and 5.7 minutes have been reported(7). Biodegredation in water is moderate(SRC) as indicated by a theoretical BOD in freshwater of 50% after 10 days(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-phenyl-1-naphthylamine, which has an extrapolated vapor pressure of 1.1X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase N-phenyl-1-naphthylamine 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 1 hr(SRC), calculated from its rate constant of 3.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase N-phenyl-1-naphthylamine may be removed from the air by wet and dry deposition(SRC). Based on its uv adsorption spectrum, direct photolysis of this compound is expected(4).

The rate constant for the vapor-phase reaction of N-phenyl-1-naphthylamine with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.1 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). N-Phenyl-1-naphthylamine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Based on its UV adsorption spectrum, direct photolysis of this compound is expected(3); measured photochemical degradation half-lives in water of 8.4 and 5.7 minutes have been reported(4).

1.70e+03|BCF ranges of 427-2,730 and 889 to 2,490 at 0.1 and 0.01 mg/L, respectively, were measured for N-phenyl-1-naphthylamine(SRC), using orange-red killifish (Oryzias latipes) which were exposed over an 8-week period(1). BCFs ranging from 432 to 1,285 (relative to radioactivity) and 233 to 694 (relative to test compound) were determined in a flow-through system for bluegill sunfish (Lepomis macrochirus) at steady state(2). According to a classification scheme(3), these BCF values suggest bioconcentration in aquatic organisms is high to very high(SRC), provided the compound is not altered physically or chemically once released into the environment.

The Koc of N-phenyl-1-naphthylamine is estimated as 4,600(SRC), using a measured log Kow of 4.2(1), and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that N-phenyl-1-naphthylamine is expected to have slight mobility in soil. The pKa of N-phenyl-1-naphthylamine is 4.93 at 25 °C(4) indicating that this compound will partially exist in the cation form in the environment(3) Since N-phenyl-1-napthylamine exists in the protonated form, it will adsorb more strongly to organic carbon and clay than its neutral counterparts(5).

The Henry's Law constant for N-phenyl-1-naphthylamine is estimated as 1.4X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.13X10-5 mm Hg(1), and water solubility, 60 mg/L(2). This Henry's Law constant indicates that N-phenyl-1-naphthylamine is expected to be essentially nonvolatile from water surfaces(3). N-Phenyl-1-naphthylamine's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). N-Phenyl-1-naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

SURFACE WATER: N-Phenyl-1-naphthylamine was identified, not quantified, in water samples from the Providence River and estuarine samples from Narragansett Bay, Massachusetts(1,2). The compound was detected, not quantified in Lake Erie's Conneaut River, Rocky River, and Black River(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 184,126 workers (16,560 of these are female) are potentially exposed to N-phenyl-1-naphthylamine in the US(1). Occupational exposure to N-phenyl-1-naphthylamine may occur through inhalation and dermal contact with this compound at workplaces where N-phenyl-1-naphthylamine is produced or used(SRC). Monitoring data indicate that the general population may be exposed to N-phenyl-1-naphthylamine via ingestion of contaminated water(SRC).

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)|Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)

In male Sprague-Dawley rats administered a single oral dose of 160 mg [14C] N-phenyl-1-naphthylamine/kg bw, the chemical was well absorbed, metabolized almost completely, and excreted primarily in the feces. Radioactivity was detected in plasma within 60 min, with the maximum concentration measured after 4 hr. After 24 hr, 20% of the radioactivity was found in the GI tract (including contents), 2.4% in fatty tissue, 0.4% in the liver, and 0.1% in the kidneys. 90% of the administered radioactivity was excreted within 48 hr; 95% was excreted within 72 hr (60% in the feces and 35% in the urine).|High performance liquid chromatographic and gas chromatographic methods for the determination of N-phenyl-1-naphthylamine (I) in biological fluid and tissues were developed, and the biological fate of I was studied in male rats following single and multiple oral administration. It was assumed that the intestinal absorption of I was excellent, because the fecal excretion of unchanged I was extremely low (0.4% of dose), and there was little unchanged I excreted in the urine (0.01% of dose). A large amount of glucuronide and sulfate metabolites was excreted in the urine. After single or multiple (6 days) oral administration, a small amount of unchanged I was distributed in fat, but the distribution of unchanged I in liver, kidney, spleen, heart and lung was extremely low.

Mono- and dihydroxy-derivatives of N-phenyl-1-naphthylamine have been identified in in vitro metabolic studies conducted with rat liver microsomes. /It was/ suggested that the hydroxyl group in the mono-hydroxy derivative is in the naphthalene moiety at a para-position to the amino group, whereas at least one hydroxyl group in the dihydroxy-derivative is at the available para-position in the naphthyl ring. Pretreatment of male rats with phenobarbital or 3-methylcholanthrene increased the rate of microsomal metabolism, indicating that more than one P-450 enzyme is involved in the metabolism of N-phenyl-1-naphthylamine.|...In the ether extract of the urine /of male Sprague-Dawley rats administered a single oral dose of 160 mg [14C] N-phenyl-1-naphthylamine/kg bw/, at least five radioactive metabolites were detected but not identified.|In studies conducted with human volunteers or laboratory animals, the isomer N-phenyl-2-naphthylamine was partially metabolized to the known human carcinogen 2-naphthylamine following ingestion or inhalation. Although data concerning the formation of this metabolite are not available for N-phenyl-1-naphthylamine, it should be noted that, based on its chemical structure, it is unlikely that N-phenyl-1-naphthylamine is metabolized to 2-naphthylamine. /N-phenyl-2-naphthylamine/

In male Sprague-Dawley rats administered a single oral dose of 160 mg [14C] N-phenyl-1-naphthylamine/kg bw, ...the elimination half-lives were reported as 1.68 hr for the fast elimination and 33 hr for the slow elimination.

The commercial product has a typical purity of >99%. Named impurities from three manufacturers are 1-naphthylamine (<100-500 mg/kg), 2-naphthylamine (<3-50 mg/kg), aniline (<100-2500 mg/kg), 1-naphthol (<5000 mg/kg), 1,1-dinaphthylamine (<1000 mg/kg), and N-phenyl-2-naphthylamine (500-<5000 mg/kg).

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/HUMAN EXPOSURE STUDIES/ N-Phenyl-1-naphthylamine, mixed with oil or water, was not irritating when applied to the skin of volunteers (no data on concentrations available). Skin eczema in workers has been attributed to repeated exposure to high levels of N-phenyl-1-naphthylamine, possibly in combination with other substances. Reportedly, the content of N-phenyl-1-naphthylamine in a special antirust oil had to be lowered from 2% to 0.5% because of skin problems. Workers, who did not wear gloves, were exposed during the packaging of bearing rings covered with antirust-oil containing N-phenyl-1-naphthylamine.|/SIGNS AND SYMPTOMS/ Acute hazards/Symptoms of Inhalation exposure: Blue lips or finger nails. Blue skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness. /from table/|/CASE REPORTS/ At a manufacturing firm making rollers for conveyor belts, the lubricant used was a fire resistant (FR) grease. Alvania Grease-RA was also used. It appeared that three employees were suffering from contact dermatitis and were patch tested. Two were allergic to phenyl-alpha-naphthylamine (PAN) which was present in both greases at 1%. There was no cross reactivity demonstrated with other naphthylamines. Brief histories of the two workers were provided. One was a 58 yr old welder and the other was a 61 yr old roller assembly worker. Despite improved protection for each of these workers, they continue to be afflicted by eczema. One required regular moderately potent topical applications of a steroid to control the condition. Both were diagnosed as having developed allergic contact dermatitis from the FR and Alvania greases as a result of sensitization to PAN, and also aryl phosphate ester mix in the second case. The authors note that testing with the routinely available phenyl-beta-naphthylamine and di-beta-naphthyl-p-phenylenediamine is not an adequate screen for detecting PAN sensitivity. They emphasize the risk of extrapolating data from animal models.|/CASE REPORTS/ N-Phenyl-1-naphthylamine was also reported to have sensitizing properties in humans. Case-studies on patients with contact dermatitis, potentially associated with occupational exposure to N-phenyl-1-naphthylamine in greases or oils, have been identified. The majority of these patients also had a positive reaction to other substances in the test series, such as mercaptobenzothiazole or p-phenylenediamine. Lower incidences were reported in patients with past exposure to rubber materials. Because of the chemical's incorporation into the polymer matrix, exposure to N-phenyl-1-naphthylamine in rubber materials is assumed to be lower than exposure from greases or oils.|/EPIDEMIOLOGY STUDIES/ An increased occurrence of cancers in a small packaging unit in a Swedish engineering company was reported in a cohort study. Between 1954 and 1957, a special anticorrosive oil, which contained 0.5% N-phenyl-1-naphthylamine in addition to other chemicals, had been used in this unit. In 12 of 78 women in this unit (group A: 78 women/20 men), cancers were diagnosed between 1964 and 1973 in several organs (predominantly the uterus and ovary). The staff performing the actual packaging, and thus in contact with the oil, were mainly women. Morbidity and mortality from cancer were 3.1- and 3.5-fold higher, respectively, than expected, based upon age-specific and sex-specific data from the Swedish Cancer Register (the standard cancer rates for the period 1974-1976 were estimated on the basis of the 1973 rate). In the males of group A, no significant differences were established. In another unit (reference group B: 25 women/8 men) where anticorrosive oil without N-phenyl-1-naphthylamine had been used, morbidity and mortality from cancer were not elevated. This was also true for reference group C (8 women/23 men), from units that had been in contact with N-phenyl-1-naphthylamine-containing anticorrosive oil for a short period of time only, because they had demonstrated allergic reactions. The authors concluded that, apart from exposure to N-phenyl-1-naphthylamine, the formation of N-nitroso-N-phenyl-1-naphthylamine from sodium nitrite originating from the packaging paper used may be a possible explanation for the increased frequency of cancer in group A.

1-anilinonaphthalene

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.

MAY BE ABSORBED!

Trade names: Antioxidant PAN; Neozone A; Nonox AN.|The commercial product has a typical purity of >99%.

All other chemical product and preparation manufacturing|1-Naphthalenamine, N-phenyl-: ACTIVE

Method: OSHA 96; Procedure: high performance liquid chromatography using fluorescence detector; Analyte: N-phenyl-1-naphthylamine; Matrix: air; Reliable Quantitatioin Limit: 17 ppt (150 nanogram/cu m).|N-Phenyl-1-naphthylamine is quantified in environmental media either by high-performance liquid chromatography in combination with ultraviolet absorption or by gas chromatography combined with thermionic or mass spectrometric detection, flame ionization detection, or electron capture detection. A method for the determination of secondary amines in air is suitable for the detection of N-phenyl-1-naphthylamine. ... Detection limits range from 0.1 to 1 ug/litre for water and from 50 to 100 ug/kg for sediment; detection limits for biological materials were not identified.