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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 8679Generated: October 23, 2026

N-phenyl-2-naphthylamine

N-PHENYL-2-NAPHTHYLAMINE · N-phenylnaphthalen-2-amine · Nonox D · 2-Naphthalenamine, N-phenyl- · N-Phenyl-2-naphthalenamine · N-PHENYL-BETA-NAPHTHYLAMINE · Neozone · N-Phenyl-Beta-Naphtylamine

https://huagongshe.com/en/chemical/8679

N-phenyl-2-naphthylamine molecular structure

Identifiers & Physical Properties

CAS No.135-88-6
Molecular formulaC16H13N
Average molar mass219.28 g/mol
Monoisotopic mass219.10479942 g/mol
SMILESc1ccc(Nc2ccc3ccccc3c2)cc1
InChIKeyKEQFTVQCIQJIQW-UHFFFAOYSA-N
PubChem CID8679
ChEMBLCHEMBL1543632
ChEBICHEBI:34877
EC No.205-223-9
DTXSIDDTXSID4021131

Chemical & Physical Properties

XLogP5.1
Topological polar surface area12
Hydrogen bond donors1
Hydrogen bond acceptors1
Rotatable bonds2
Heavy atoms17
Formal charge0
Complexity232
LogP (partition coefficient)log Kow = 4.38
Density1.24 (NTP, 1992) - Denser than waterwill sink1.2 g/cm³
Color/FormNEEDLES FROM METHANOLWHITE TO YELLOWISH CRYSTALSGRAY TO TAN FLAKES OR POWDERWhite to yellow crystals or gray tan flakes or powder [Note: Commercial product may contain 20-30 ppm of beta naphthylamine].
Solubilityless than 1 mg/mL at 66 °F (NTP, 1992)SOLUBILITY IN ETHANOL 50 G/L, IN BENZENE 27 G/L, IN ACETONE 640 G/LINSOL IN WATERSOL IN ALC, ETHER, ACETIC ACID (BLUISH FLUORESCENCE)Solubility in water at 25 °C: noneInsolubleChloroform (Slightly), Methanol (Very Slightly)Insoluble. <0.1 g/100 mL at 19 ºC
Boiling point743 °F at 760 mmHg (NTP, 1992)395.5 °C395-395.5 °C (lit.)
DecompositionWHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF /NITROGEN OXIDES/.
Melting point226 °F (NTP, 1992)108 °C105-108 °C (lit.)
Vapor pressure0.00000829 [mmHg]0.001Pa at 20℃
Physical DescriptionN-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]SolidWHITE-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.]
Kovats Retention Index21692222
Collision Cross Section151.3 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID4021131]149.2 Ų [M]+ [CCS Type: DTIonization: APCI+150.0 Ų [M+H]+ [CCS Type: DT
Other Experimental PropertiesMAY BE OXIDIZED TO 7-PHENYL-7H-DIBENZO[C,G]CARBAZOLE
Refractive index1.7020 (estimate)
Storage conditions-20°C
pKa (acidity coefficient)0.78±0.30(Predicted)
Physical stateGray to tan flakes or powder
ColorPale Beige to Pale Gray
Biological sourcemouse
λmax219 nm
BRN2211188
StabilityStable. Incompatible with oxidizing agents.
InChI1S/C16H13N/c1-2-8-15(9-3-1)17-16-11-10-13-6-4-5-7-14(13)12-16/h1-12,17H
InChIKeyKEQFTVQCIQJIQW-UHFFFAOYSA-N
SMILESN(c1ccccc1)c2ccc3ccccc3c2
LogP (partition coefficient)3.2 at 23℃ and pH7.9-8.3
Toxicology and CarcinogenesisToxicology and Carcinogenesis Studies of N-Phenyl-2-Naphthylamine (CASRN 135-88-6) in F344/N Rats and B6C3F1 Mice (Feed Studies)
FDA 21 CFR175.105176.170177.2600
Indirect Additives used in Food Contact SubstancesPHENYL-BETA-NAPHTHYLAMINE (FREE OF BETA-NAPHTHYLAMINE)
CAS DataBase Reference135-88-6(CAS DataBase Reference)
EWG's Food Scores3-4
FDA UNII456KT854AJ
NIST Chemistry Reference2-Naphthyl phenyl amine(135-88-6)
IARC3 (Vol. 16, Sup 7) 1987
EPA Substance Registry SystemN-Phenyl-2-naphthylamine (135-88-6)
UNSPSC Code12352203
NACRESNA.41
GHS pictogramGHS07,GHS08,GHS09
Signal wordWarning
GHS hazard statementsH315-H319-H317-H351-H411
GHS precautionary statementsP501-P261-P273-P272-P202-P201-P264-P280-P302+P352-P391-P308+P313-P337+P313-P305+P351+P338-P362+P364-P333+P313-P405
Personal protective equipment (PPE)Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard symbolsXn,N
Risk statements (R)36/38-40-43-51/53-53-51
Safety statements (S)22-24/25-61-36/37-26
UN transport number3077
Water hazard class (WGK)2
RTECS numberQM4550000
TSCA inventory statusTSCA listed
Hazard class6.1(b)Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
Packing groupIII
Customs code29214500
Storage class11 - Combustible Solids
Hazardous substances data135-88-6(Hazardous Substances Data)
Toxicitymouse,LD50,oral,1450mg/kg (1450mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Hygiene and Sanitation Vol. 31(1-3), Pg. 183, 1966.
REACH registrationsActive
Limited quantities5.0 kg (11 lbs) (solid)
Excepted quantitiesMax Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & Regulations

GHS classificationWarningH315: 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)
Regulatory informationChemical: 2-Naphthalenamine, N-phenyl-Status: Active Update: 10-08-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18330N-Phenyl-2-naphthylamine: Does not have an individual approval but may be used under an appropriate group standard
Other safety informationIMAP assessments - 2-Naphthalenamine, N-phenyl-: Human health tier II assessment
DOT labelCorrosive
Fire hazardsLiterature sources indicate that this chemical is combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air.
Fire potentialFIRE HAZARD: MODERATE, WHEN EXPOSED TO HEAT OR FLAME... CAN REACT WITH OXIDIZING MATERIALS.
Health hazardsExcerpt from NIOSH Pocket Guide for N-Phenyl-beta-naphthylamine:Exposure Routes: Inhalation, skin absorption, ingestion, skin and/or eye contactSymptoms: Irritationleucoplakiaacne, hypersensitivity to sunlight[potential occupational carcinogen]Target Organs: Eyes, skin, bladderCancer Site: Bladder cancer (NIOSH, 2024)
Hazards summaryAllergic contact dermatitis reported in rubber workers[Kanerva, p. 1826] Danger of skin sensitization[MAK]
Reactive groupAmines, Phosphines, and Pyridines
UN classificationUN Hazard Class: 9UN Pack Group: III
Special ReportsDHHS/NTPToxicology & 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. 88-2589DISCUSSES CARCINOGENIC RISK OF PBNA TO HUMAN SUBJECTS.[BATTEN PL, HATHWAY DEBR J CANCER 35 (3): 342-346 (1977)]Scmidt E et alZeitschr Gesamte Hyg 29 (8): 452-6 (1983). Toxicological evaluation of vulcanization vapors with special reference to nitrogen containing aging preventative agents.
Reactivity ProfileN-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.
Chemical DangersReacts with oxidants. Decomposes on burning. This produces toxic and corrosive fumes.
Fire fightingFires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder, foam, carbon dioxide.
First aid measuresFresh 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.
First aidEYES: 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 areatake 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 usedif 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 supportSwallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.
Safe storageSeparated from oxidants. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
Storage conditions...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.
Nonfire spill responseSMALL 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)
Disposal methodsSRP: 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.
Spillage disposalPersonal 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.
Preventive MeasuresThe 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.
Isolation and EvacuationExcerpt 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 directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)
Eye PreventionWear safety goggles.
Fire PreventionNO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. Prevent build-up of electrostatic charges (e.g., by grounding).
Cancer Sites[bladder cancer]
Target organsEyes, skin, bladder
Environmental fateTERRESTRIAL 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 sedimenttherefore, 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).
Adverse effectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.ACGIH Carcinogen - Not Classifiable.
Exposure routesThe substance can be absorbed into the body by inhalation, by ingestion and through the skin.inhalation, skin absorption, ingestion, skin and/or eye contact
Signs and SymptomsRedness.Redness. Pain.Irritationleucoplakiaacne, hypersensitivity to sunlight[potential occupational carcinogen]
Ongoing Test StatusThe 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]
ICSC Environmental DataThe substance is toxic to aquatic organisms. Bioaccumulation of this chemical may occur in fish. The substance may cause long-term effects in the aquatic environment.
Soil Adsorption/MobilityAromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solutionthe 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 quinonethese 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.
Human Toxicity ExcerptsLEUCOPLAKIA, 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.
Artificial Pollution SourcesN-Phenyl-2-naphthylamine is used as an antioxidant, lubricant, and inhibitor(1) and, therefore, it may be released to the environment during its production and use(SRC).
Environmental BiodegradationUsing 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).
Personal protective equipment (PPE)Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Water hazard class (WGK)2
TSCA inventory statusTSCA listed
RTECS numberQM4550000
UN transport number3077
Customs code29214500
Toxicitymouse,LD50,oral,1450mg/kg (1450mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Hygiene and Sanitation Vol. 31(1-3), Pg. 183, 1966.
Risk statements (R)36/38-40-43-51/53-53-51
Signal wordWarning
GHS pictogramGHS07,GHS08,GHS09
Hazard symbolsXn,N
Safety statements (S)22-24/25-61-36/37-26
Hazard class6.1(b)Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
Storage class11 - Combustible Solids
Packing groupIII
GHS hazard statementsH315-H319-H317-H351-H411
Limited quantities5.0 kg (11 lbs) (solid)
Excepted quantitiesMax Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH registrationsActive
GHS precautionary statementsP501-P261-P273-P272-P202-P201-P264-P280-P302+P352-P391-P308+P313-P337+P313-P305+P351+P338-P362+P364-P333+P313-P405
Hazardous substances data135-88-6(Hazardous Substances Data)

Applications & Uses

Description

Phenyl-naphtylamine is an amine coumpound. Sensitization was reported in patients with hypersensitivity to rubber.

Uses

N-Phenyl-2-naphthylamine is used as an antioxidant in rubber processing; provides oxidation and flex-cracking resistance in natural rubber, synthetic rubbers, and latexes; stabilizer in electrical-insulating silicone enamels; antioxidant in otiJer polymers, greases, lubricating oils, and transformer oils; heat and light stabilizer; vulcanization accelerator; catalyst; polymerization inhibitor; component of rocket fuels, surgical plasters, and tin-electroplating batiJs; chemical intermediate; an inhibitor for butadiene; in the production of seven dyes; in rubber products made of natural rubber, styrene-butadiene, nitrile, butadiene, and chloroprene.

Uses

Formerly as an antioxidant in rubber processing to impart heat, oxidation, and flexcracking resistance in natural rubber, synthetic rubbers, and latexes; as a stabilizer in electricalinsulating silicone enamels

Uses

Formerly as an antioxidant in rubber processing to impart heat, oxidation, and flexcracking resistance in natural rubber, synthetic rubbers, and latexes; as a stabilizer in electricalinsulating silicone enamels

General Description

Light gray to gray powder. Solutions show blue fluorescence.