N-Naphthylanilin

log Kow = 4.38

4.38

4.38

1.24 (NTP, 1992) - Denser than water; will sink

1.24

1.2 g/cm³

1.24

1.24

NEEDLES FROM METHANOL

WHITE TO YELLOWISH CRYSTALS

GRAY TO TAN FLAKES OR POWDER

White to yellow crystals or gray tan flakes or powder [Note: Commercial product may contain 20-30 ppm of beta naphthylamine].

less than 1 mg/mL at 66 °F (NTP, 1992)

SOLUBILITY IN ETHANOL 50 G/L, IN BENZENE 27 G/L, IN ACETONE 640 G/L

INSOL IN WATER; SOL IN ALC, ETHER, ACETIC ACID (BLUISH FLUORESCENCE)

Solubility in water at 25 °C: none

Insoluble

743 °F at 760 mmHg (NTP, 1992)

395.5 °C

395.5 °C

743 °F

743 °F

226 °F (NTP, 1992)

108 °C

108 °C

108 °C

226 °F

226 °F

N-phenyl-2-naphthylamine is a light gray to gray powder. Solutions show blue fluorescence. (NTP, 1992)

White to yellow crystals or gray to tan flakes or powder. [Note: Commercial product may contain 20-30 ppm of Beta-Naphthylamine.]; [NIOSH]

Solid

WHITE-TO-GREY SOLID IN VARIOUS FORMS.

White to yellow crystals or gray to tan flakes or powder.

White to yellow crystals or gray to tan flakes or powder. [Note: Commercial product may contain 20-30 ppm of β-Naphthylamine.]

2169

2222

151.3 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4021131]；149.2 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID4021131]；150.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID4021131]

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]；H317: May cause an allergic skin reaction [Warning Sensitization, Skin]；H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H351: Suspected of causing cancer [Warning Carcinogenicity]；H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P203, P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Warning

Chemical: 2-Naphthalenamine, N-phenyl-

Status: Active Update: 10-08-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18330

N-Phenyl-2-naphthylamine: Does not have an individual approval but may be used under an appropriate group standard

Literature sources indicate that this chemical is combustible. (NTP, 1992)

Combustible. Finely dispersed particles form explosive mixtures in air.

Excerpt from NIOSH Pocket Guide for N-Phenyl-beta-naphthylamine:；Exposure Routes: Inhalation, skin absorption, ingestion, skin and/or eye contact；Symptoms: Irritation; leucoplakia; acne, hypersensitivity to sunlight; [potential occupational carcinogen]；Target Organs: Eyes, skin, bladder；Cancer Site: Bladder cancer (NIOSH, 2024)

DHHS/NTP; Toxicology & Carcinogenesis Studies of N-Phenyl-2-naphthylamine in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 333 (1988) NIH Publication No. 88-2589

DISCUSSES CARCINOGENIC RISK OF PBNA TO HUMAN SUBJECTS.[BATTEN PL, HATHWAY DE; BR J CANCER 35 (3): 342-346 (1977)]

Scmidt E et al; Zeitschr Gesamte Hyg 29 (8): 452-6 (1983). Toxicological evaluation of vulcanization vapors with special reference to nitrogen containing aging preventative agents.

N-PHENYL-2-NAPHTHYLAMINE may react with strong oxidizing agents (NTP, 1992). 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.

Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest. Seek medical attention if you feel unwell.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

Seek medical attention if you feel unwell.

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)

(General first aid procedures)；Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.；Skin: Soap wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.；Breathing: Respiratory support；Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH...DECOMP INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT...SHOULD BE STORED IN COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, &...PERIODICALLY INSPECTED & MONITORED.

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 store this material under ambient temperatures and protect it from light. (NTP, 1992)

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.

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 containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

The worker should immediately wash the skin when it becomes contaminated.

The worker should wash daily at the end of each work shift.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:；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 the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank 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, 2024)

TERRESTRIAL FATE: One screening study observed that N-phenyl-2-naphthylamine is readily biodegradable to beta-naphthylamine at concns <5 ppm(2). Higher concns appear to be toxic to microorganisms(2,SRC). Because N-phenyl-2-naphthylamine absorbs UV light >290 nm(3), photolysis may be important if N-phenyl-2-naphthylamine is spilled on terrestrial surfaces(SRC). By analogy to other aromatic amines(1), when released to soil, N-phenyl-2-naphthylamine may undergo covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and result in tight adsorption. When covalently bound in this latent form, leaching in soil systems is not expected to occur. This covalent bonding proceeds in two steps: a rapid and reversible bonding followed by a slower and much less reversible reaction(1,SRC). In the absence of covalent bonding, leaching would not be possible based on an estimated Koc of 12,500(4-6).

AQUATIC FATE: Based on analogy to other aromatic amines(1), N-phenyl-2-naphthylamine may undergo covalent bonding with humic materials in the water column and in sediment; therefore, partitioning from the water column to sediment and suspended material may be important. N-Phenyl-2-naphthylamine may be susceptible to photooxidation via hydroxyl and peroxy radicals based on analogy to other aromatic amines(2,SRC). Because N-phenyl-2-naphthylamine abosorbs UV light >290 nm(4), photolysis may be important in near-surface water. A BCF value of 147(3,SRC) suggests that N-phenyl-2-naphthylamine will have low potential to bioconcentrate in aquatic organisms(SRC). Aquatic hydrolysis and volatilization do not appear to be environmentally important removal processes of N-phenyl-2-naphthylamine in water(SRC). It appears that N-phenyl-2-naphthylamine is readily biodegradable to beta-naphthylamine at concns <5 ppm(5).

ATMOSPHERIC FATE: Based on a modified regression-derived equation(1,SRC), the vapor pressure for N-phenyl-2-naphthylamine can be estimated to be 8.3X10-6 mm Hg at 25 °C(SRC). According to a suggested classification scheme(2), this vapor pressure value suggests that N-phenyl-2-naphthylamine will exist in both the vapor and particulate phases in the ambient atmosphere. Particulate-phase N-phenyl-2-naphthylamine will probably be removed from air via dry deposition. Vapor-phase N- phenyl-2-naphthylamine is degraded rapidly in an average ambient atmosphere by reaction with photochemically produced hydroxyl radicals at an estimated half-life of about 55 minutes(3,SRC).

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

inhalation, skin absorption, ingestion, skin and/or eye contact

Redness.

Redness. Pain.

Irritation; leucoplakia; acne, hypersensitivity to sunlight; [potential occupational carcinogen]

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=135-88-6]

Aromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(4). In the absence of covalent bonding, one can estimate the adsorption potential based on the Koc value. Based on an experimental log octanol-water partition coefficient of 4.38(2) and a recommended regression-derived equation(1), the Koc value for N-phenyl-2-naphthylamine can be estimated to be 12,500(SRC). According to a suggested classification scheme(3), this Koc value indicates that N-phenyl-2-naphthylamine will be immobile in soil.

LEUCOPLAKIA, ACNE & HYPERSENSITIVITY TO SUNLIGHT...OBSERVED IN 36 WORKERS EXPOSED FOR PROLONGED PERIODS TO N-PHENYL-2-NAPHTHYLAMINE...

OUT OF 57 CU-SMELTING WORKERS SUFFERING FROM INFLAMMATORY LESIONS OF MUCOUS MEMBRANE & SKIN OF LIPS, 22 HAD INCR SENSITIVITY TO RUBBER AS MAIN CAUSE OF CHEILITIS.

OCCUPATIONAL ALLERGIC DERMATOSIS WAS OBSERVED IN RUBBER WORKERS DUE TO ADDITIVES SUCH AS NEOZON D.

IT HAS BEEN REPORTED THAT COMMERCIAL N-PHENYL-2-NAPHTHYLAMINE IS CONTAMINATED WITH 20-30 MG/KG OF CARCINOGEN 2-NAPHTHYLAMINE...

For more Human Toxicity Excerpts (Complete) data for 2-NAPHTHYLAMINE, N-PHENYL- (6 total), please visit the HSDB record page.

Using an initial concn of 100 mg/L N-phenyl-2-naphthylamine, 0 %BOD was observed after a 2 week period in a biodegradation screening test using 30 mg/L sludge(1). N-Phenyl-2-naphthylamine, initial concn of 100 ppm, exhibited a 0-29 % Theoretical BOD in a Japanese MITI test after 14 days of incubation at 25 °C(2). N-phenyl-2-naphthylamine was shown to degrade to beta-naphthylamine in a screening study using activated sludge inoculum at 21 °C(3). In this study, 44.2 and 9.3 %CO2 production was observed in 1 day at initial concns of 2 and 5 ppm, respectively(3). At an initial concn of 8 ppm, N-phenyl-2-naphthylamine was observed to be inhibitory to microorganisms under the same test conditions(3). Furthermore, adsorption to solids was found to occur and, hence, reduce biodegradation(3).

Chemical: 2-Naphthalenamine, N-phenyl-

Status: Active Update: 10-08-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18330

N-Phenyl-2-naphthylamine: Does not have an individual approval but may be used under an appropriate group standard

AMT RANGING FROM 0-10 UG 2-NAPHTHYLAMINE WAS DETECTED IN URINE OF DOGS GIVEN SINGLE DOSE OF 5 MG/KG...N-PHENYL-2-NAPHTHYLAMINE...

Hepatic microsomal preparations from rat, hamster, dog, monkey, and humans catalyze PBNA biotransformation in vitro to 6-hydroxy-N-phenyl-2-naphthylamine and 4'-hydroxy-N-phenyl-2-naphthylamine.

A dose dependent relationship between the concn of parent compound and its BNA metabolite in rat urine was observed after oral doses of 50 or 100 mg PBNA/kg/day for 4 days. Some 34 ug BNA was recovered in rat urine after a total PBNA dose of 400 mg.

Experimental evidence from human volunteers ingesting PBNA at a single 10-50 mg dose and from workers inhaling PBNA dust show that BNA is eliminated in the urine as a metabolite of PBNA.

The carcinogenic antioxidants, N-phenyl-1-naphthylamine (P1NA) and phenyl-2-naphthylamine (P2NA) were examined in vitro for biotransformation by rat hepatic microsomes and in freshly isolated hepatocytes. HLPC analysis of hepatocyte incubations revealed that phenols were the major metabolites in both cases. P1NA formed one phenolic metabolite only, while incubation with P2NA yielded two phenols identified as 6-hydroxy-P2NA and 4'-hydroxy-P2NA by chromatography with authentic samples. beta-Naphthylamine, a metabolite indicating dephenylation of P2NA was not detectable. Metabolism studies with microsomes revealed that the phenols were formed by cytochrome p450 dependent monooxygenases. Pretreatment of animals with phenobarbital and 3-methylcholanthrene both incr the rate of microsomal metabolism of P1NA and P2NA, indicating that more than one p450 enzyme mediate the oxygenation reaction. Animal pretreatment with single and repeated doses of P1NA and P2NA did not markedly stimulate metabolism, but induced ethylmorphine demethylation in males and females and benzo(a)pyrene hydroxylation in females.

IN DOGS GIVEN SINGLE ORAL DOSES OF 5 MG/KG...(1,4,5 ,8-(14)C)-N-PHENYL-2-NAPHTHYLAMINE ALONE OR FOLLOWING REPEATED DOSES OF 400 MG/ANIMAL...N-PHENYL-2-NAPHTHYLAMINE ON 5 DAYS A WK FOR 4 WK, MORE THAN 90% OF RADIOACTIVITY...EXCRETED OVER 3 DAYS, MAINLY IN FECES. ONLY 2.8% OF RADIOACTIVITY WAS EXCRETED IN URINE.

NO INCR EXCRETION OF LABELED 2-NAPHTHYLAMINE...OBSERVED FOLLOWING 4 WK PRETREATMENT WITH 400 MG/ANIMAL UNLABELED N-PHENYL-2-NAPHTHYLAMINE...

2-NAPHTHYLAMINE WAS FOUND @ LEVEL OF 3-4 UG IN 24-HR SAMPLES OF URINE FROM 2 VOLUNTEERS WHO INGESTED 50 MG N-PHENYL-2-NAPHTHYLAMINE CONTAINING 0.7 UG 2-NAPHTHYLAMINE & FROM WORKERS (UNSPECIFIED NUMBER) EST TO HAVE INHALED 30 MG N-PHENYL-2-NAPHTHYLAMINE...

IN 4 WORKERS EXPOSED TO N-PHENYL-2-NAPHTHYLAMINE DUSTS (EST INTAKE, 40 MG)... EST TO CONTAIN 32 NG 2-NAPHTHYLAMINE, 3-8 UG 2-NAPHTHYLAMINE...FOUND IN 24-HR URINE SAMPLES...

IN 19 VOLUNTEERS GIVEN 10 MG N-PHENYL-2-NAPHTHYLAMINE CONTAINING 8 NG 2-NAPHTHYLAMINE (0.8 MG/KG), FROM 0.4-3 UG 2-NAPHTHYLAMINE WERE FOUND IN 24-HR URINE SAMPLES FROM 7 SUBJECTS, 6 OF WHICH WERE NON-SMOKERS.

No longer used in the United States because of carcinogenic potential; in the past used as a antioxidant for rubber, grease, and oils; also used as a component of rocket fuels and as a stabilizer in dyes and silicone enamels; [ACGIH] Used as an antioxidant in the production of rubber, polymers, greases, oils; as an inhibitor of polymerization; as a stabilizer in silicon enamels; and as a catalyst and chemical intermediate; Also used in rocket fuels, surgical plasters, and tin electroplating baths; [CHEMINFO]

Electroplating [Category: Plate]

RUBBER ANTIOXIDANT; LUBRICANT; INHIBITOR (BUTADIENE)

STABILIZER IN ELECTRICAL-INSULATING SILICONE ENAMELS; HEAT & LIGHT STABILIZER; VULCANIZATION ACCELERATOR; COMPONENT OF ROCKET FUELS; IN SURGICAL PLASTERS; IN TIN-ELECTROPLATING BATHS; CHEM INTERMEDIATE; IN DYES; CATALYST & POLYMERIZATION INHIBITOR

(1972) No Data

(1975) No Data

(1972) 4.00X10+5 GRAMS

(1975) 7.58X10+7 GRAMS

Imports through the principal U.S. customs districts totaled 18,166 pounds in 1983.

(1972) 2.05X10+9 GRAMS

(1975) 7.09X10+8 GRAMS

...WAS PREPARED BY GRAEBE IN 1880 BY HEATING 2-NAPHTHOL WITH ANILINE HYDROCHLORIDE (PRAGER ET AL, 1929). METHOD...CURRENTLY...USED IN JAPAN (THE CHEM DAILY CO LTD, 1976) & IN US (KEHE & KOURIS, 1965) IS CONDENSATION OF 2-NAPHTHOL & ANILINE IN PRESENCE OF A CATALYST.

UNTIL RECENTLY...WAS AVAILABLE IN US AS COMMERCIAL GRADE...PURITY, 97.0% MIN; SET-POINT, 106.0 °C MIN; ASH CONTENT, 0.5% MAX; 2-NAPHTHOL CONTENT, 0.5% MAX.

/IT IS/...AVAILABLE IN US IN VARIETY OF FORMULATIONS, COMPOUNDED WITH OTHER ANTIOXIDANTS, EG, PARA-ISOPROPOXYDIPHENYLAMINE & DIPHENYL-PARA-PHENYLENEDIAMINE...

2-Naphthalenamine, N-phenyl-: ACTIVE

...DETECTED IN EXTRACTS FROM WIDE VARIETY OF ANIMAL, PLANT & MICROBIAL LIPIDS. IT HAS BEEN SHOWN, HOWEVER, THAT IT WAS CONTAMINANT OF SOLVENTS USED TO EXTRACT THEM, WHICH HAD COME INTO CONTACT WITH RUBBER CONTAINING THE ANTIOXIDANT...

IT IS BELIEVED THAT NO US COMPANIES ARE CURRENTLY PRODUCING THIS COMPD COMMERCIALLY

...IS USED PRIMARILY AS ANTIOXIDANT (GENERALLY @ LEVELS OF 1-2%) IN RUBBER PROCESSING...TO IMPART HEAT, OXIDN & FLEX-CRACKING RESISTANCE IN NATURAL RUBBER, SYNTHETIC RUBBERS & LATEXES...

.../IT/ HAS BEEN USED AS CHEM INTERMEDIATE IN PRODN OF RUBBER ANTIOXIDANT, N-PHENYL-2-NAPHTHYLAMINE-ACETONE CONDENSATE, & IN PRODN OF 7 DYES...OF WHICH...CI ACID BLUE 98.../IS/ OF COMMERCIAL WORLD SIGNIFICANCE...

N-Phenyl-2-naphthylamine, an antioxidant in rubber processing, is gradually being displaced by improved products.