Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
N-페닐-2-나프틸아민
2-나프틸아민,N-페닐- · N-페닐-2-나프틸아민 · N-페닐-베타-나프틸아민 · N-2-나프틸아닐린 · 2-나프틸아민, N-페닐- · N-(2-나프틸)아닐린 · N-PHENYL-2-NAPHTHYLAMINE · N-phenylnaphthalen-2-amine
식별자 및 물리적 특성
| CAS No. | 135-88-6 |
|---|---|
| 분자식 | C16H13N |
| 평균 분자량 | 219.28 g/mol |
| 단동위원소 질량 | 219.10479942 g/mol |
| SMILES | c1ccc(Nc2ccc3ccccc3c2)cc1 |
| InChIKey | KEQFTVQCIQJIQW-UHFFFAOYSA-N |
| PubChem CID | 8679 |
| ChEMBL | CHEMBL1543632 |
| ChEBI | CHEBI:34877 |
| EC No. | 205-223-9 |
| DTXSID | DTXSID4021131 |
| 현지명 | N-페닐-2-나프틸아민 |
화학 및 물리적 성질
| XLogP | 5.1 |
|---|---|
| 극성 표면적 | 12 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 17 |
| 형식 전하 | 0 |
| 복잡도 | 232 |
| LogP(분배 계수) | log Kow = 4.38 |
| 밀도 | 1.24 (NTP, 1992) - Denser than waterwill sink1.2 g/cm³ |
| Color/Form | NEEDLES 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]. |
| 용해도 | 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/LINSOL IN WATERSOL IN ALC, ETHER, ACETIC ACID (BLUISH FLUORESCENCE)Solubility in water at 25 °C: noneInsoluble클로로포름(약간 용해됨), 메탄올(매우 소량) |
| 끓는 점 | 743 °F at 760 mmHg (NTP, 1992)395.5 °C395-395.5 °C (lit.) |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF /NITROGEN OXIDES/. |
| 녹는점 | 226 °F (NTP, 1992)108 °C105-108 °C (lit.) |
| 증기압 | 0.00000829 [mmHg]0.001Pa at 20℃ |
| Physical Description | 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]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 Index | 21692222 |
| Collision Cross Section | 151.3 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 Properties | MAY BE OXIDIZED TO 7-PHENYL-7H-DIBENZO[C,G]CARBAZOLE |
| 굴절률 | 1.7020 (estimate) |
| 저장 조건 | -20°C |
| pKa(산도 계수) | 0.78±0.30(Predicted) |
| 물리적 상태 | 회색에서 황갈색 플레이크 또는 분말 |
| 색상 | 페일베이지부터 페일그레이까지 |
| 생물학적 소스 | mouse |
| 용해도 | 불용성. 19ºC에서 <0.1g/100mL |
| BRN | 2211188 |
| 안정성 | 안정적인. 산화제와 호환되지 않습니다. |
| InChI | 1S/C16H13N/c1-2-8-15(9-3-1)17-16-11-10-13-6-4-5-7-14(13)12-16/h1-12,17H |
| InChIKey | KEQFTVQCIQJIQW-UHFFFAOYSA-N |
| SMILES | N(c1ccccc1)c2ccc3ccccc3c2 |
| LogP(분배 계수) | 3.2 at 23℃ and pH7.9-8.3 |
| NIST | 2-Naphthyl phenyl amine(135-88-6) |
| EPA | N-Phenyl-2-naphthylamine (135-88-6) |
화학적 성질
light grey powder or crystals
안전 및 규제
| GHS 분류 | WarningH315: 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) |
|---|---|
| 규제 정보 | Chemical: 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 |
| 기타 안전 정보 | IMAP assessments - 2-Naphthalenamine, N-phenyl-: Human health tier II assessment |
| 운송 라벨(DOT) | Corrosive |
| 화재 위험 | Literature sources indicate that this chemical is combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air. |
| 화재 가능성 | FIRE HAZARD: MODERATE, WHEN EXPOSED TO HEAT OR FLAME... CAN REACT WITH OXIDIZING MATERIALS. |
| 건강 유해성 | Excerpt 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) |
| 유해성 요약 | Allergic contact dermatitis reported in rubber workers[Kanerva, p. 1826] Danger of skin sensitization[MAK] |
| 반응성 그룹 | Amines, Phosphines, and Pyridines |
| UN 분류 | UN Hazard Class: 9UN Pack Group: III |
| Special Reports | DHHS/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 Profile | 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. |
| Chemical Dangers | Reacts with oxidants. Decomposes on burning. This produces toxic and corrosive fumes. |
| 소화 | 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. |
| 응급 조치 | 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. |
| 응급 처치 | 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 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. |
| 안전 보관 | Separated from oxidants. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. |
| 보관 조건 | ...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. |
| 비화재 누출 대응 | 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) |
| 처리 방법 | 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. |
| 누출 처리 | 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. |
| Preventive Measures | 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. |
| Isolation and Evacuation | 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 directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO 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] |
| 표적 장기 | Eyes, skin, bladder |
| 환경 거동 | 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 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). |
| 유해 작용 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin.ACGIH Carcinogen - Not Classifiable. |
| 노출 경로 | 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 |
| Signs and Symptoms | Redness.Redness. Pain.Irritationleucoplakiaacne, hypersensitivity to sunlight[potential occupational carcinogen] |
| Ongoing Test Status | 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] |
| ICSC Environmental Data | The 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/Mobility | Aromatic 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 Excerpts | 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. |
| Artificial Pollution Sources | N-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 Biodegradation | 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). |
| 수질 위해 등급(WGK) | 2 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | QM4550000 |
| 운송 번호(UN) | 3077 |
| 독성 | mouse,LD50,oral,1450mg/kg (1450mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Hygiene and Sanitation Vol. 31(1-3), Pg. 183, 1966. |
| 관세 코드 | 29214500 |
| 위험 문구(R) | 36/38-40-43-51/53-53-51 |
| 위험 표시 | Xn,N |
| 안전 문구(S) | 22-24/25-61-36/37-26 |
| 포장분류 | III |
| 위험 등급 | 6.1(b)Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1 |
| 기존화학 물질 | KE-28288 |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 135-88-6(Hazardous Substances Data) |
용도
개요
Phenyl-naphtylamine is an amine coumpound. Sensitization was reported in patients with hypersensitivity to rubber.
용도
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.
일반 설명
Light gray to gray powder. Solutions show blue fluorescence.