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N-苯基-2-萘胺
尼奥宗D · 防老剂丁 · 防老剂D · 防老剂 D · 苯基乙萘胺 · 苯基Β-萘胺 · 防老剂"D" · 尼奥棕"D"
标识与物理属性
| CAS No. | 135-88-6 |
|---|---|
| 分子式 | C16H13N |
| 平均分子量 | 219.28 g/mol |
| 单同位素质量 | 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 |
| 中文名 | N-苯基-2-萘胺 |
化学与物理性质
| XLogP | 5.1 |
|---|---|
| 极性表面积 | 12 |
| 氢键供体 | 1 |
| 氢键受体 | 1 |
| 可旋转键 | 2 |
| 重原子 | 17 |
| 形式电荷 | 0 |
| 复杂度 | 232 |
| LogP（油水分配系数） | log Kow = 4.38 |
| 密度 | 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]. |
| 溶解性 | 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: noneInsolubleChloroform (Slightly), Methanol (Very Slightly)Insoluble. <0.1 g/100 mL at 19 ºC |
| 沸点 | 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/. |
| 熔点 | 226 °F (NTP, 1992)108 °C105-108 °C (lit.) |
| 蒸气压 | 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 |
| 折射率 | 1.7020 (estimate) |
| 储存条件 | -20°C |
| 形态 | Gray to tan flakes or powder |
| pKa（酸度系数） | 0.78±0.30(Predicted) |
| 颜色 | Pale Beige to Pale Gray |
| 生物来源 | mouse |
| 最大波长(λmax) | 219 nm |
| BRN | 2211188 |
| 稳定性 | Stable. Incompatible with oxidizing agents. |
| 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（油水分配系数） | 3.2 at 23℃ and pH7.9-8.3 |
| CAS 数据库 | 135-88-6(CAS DataBase Reference) |
| (IARC)致癌物分类 | 3 (Vol. 16, Sup 7) 1987 |
| NIST化学物质信息 | 2-Naphthyl phenyl amine(135-88-6) |
| EPA化学物质信息 | N-Phenyl-2-naphthylamine (135-88-6) |
化学性质
浅灰色粉末，暴露于空气中或日光下逐渐转变为灰红色。 不溶于水，溶于乙醇、四氯化碳、苯、丙酮。
安全与法规
| GHS 分类 | 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) |
|---|---|
| 法规信息 | 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 |
| 其他安全信息 | IMAP assessments - 2-Naphthalenamine, N-phenyl-: Human health tier II assessment |
| 运输标签（DOT） | Corrosive |
| 火灾危害 | Literature sources indicate that this chemical is combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air. |
| 火灾可能性 | FIRE HAZARD: MODERATE, WHEN EXPOSED TO HEAT OR FLAME... CAN REACT WITH OXIDIZING MATERIALS. |
| 健康危害 | 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) |
| 危害概述 | Allergic contact dermatitis reported in rubber workers[Kanerva, p. 1826] Danger of skin sensitization[MAK] |
| 反应性基团 | Amines, Phosphines, and Pyridines |
| 联合国分类 | 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. |
| 消防 | 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. |
| 急救措施 | 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. |
| 急救 | 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. |
| 安全储存 | Separated from oxidants. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. |
| 储存条件 | ...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. |
| 非火灾泄漏应对 | 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) |
| 处置方法 | 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. |
| 泄漏处置 | 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] |
| 靶器官 | Eyes, skin, bladder |
| 环境归趋 | 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). |
| 不良影响 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin.ACGIH Carcinogen - Not Classifiable. |
| 暴露途径 | 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). |
| 水危害等级（WGK） | 2 |
| TSCA 清单状态 | TSCA listed |
| 毒性 | mouse,LD50,oral,1450mg/kg (1450mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Hygiene and Sanitation Vol. 31(1-3), Pg. 183, 1966. |
| RTECS 号 | QM4550000 |
| 包装类别 | III |
| 危险类别 | 6.1(b)Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1 |
| 储存类别 | 11 - Combustible Solids |
| 安全说明（S） | 22-24/25-61-36/37-26 |
| 海关编码 | 29214500 |
| 危险品标志 | Xn,N |
| 危险类别码（R） | 36/38-40-43-51/53-53-51 |
| 毒害物质数据 | 135-88-6(Hazardous Substances Data) |
| 运输编号（UN） | 3077 |
用途与应用
用途
适用于天然橡胶、合成橡胶和胶乳
用途
该品是天然橡胶、二烯类合成橡胶、氯丁橡胶及基胶乳用通用型防老剂。对热、氧、屈挠及一般老化有良好的防护作用，并稍优于防老剂甲。对有害金属有抑制作用，但较防老剂甲弱。若与防老剂4010或4010NA并用，则抗热、氧、屈挠龟裂，以及抗臭氧性均有显著提高。本品对天然胶、丁腈胶、丁苯胶的硫化速度无甚影响，对氯丁胶则稍有迟延作用。本品在干胶中容易分解，亦容易分散于水中。本品在橡胶中的溶解度约1.5%，用量不超过1份不会发生喷霜。该品有污染性，在日光下渐变为灰黑色，故不适用于白色或浅色制品。主要用于制造轮胎、胶管、胶带、胶辊、胶鞋、电线电缆绝缘层等工业制品。防老剂丁还可作各种合成橡胶后处理和贮存时的稳定剂，可用作聚甲醛的抗热防老剂。该品对皮肤有一定的刺激性。
用途
检验氯酸盐。有机合成。染料中间体。用作橡胶抗氧剂、润滑剂、聚合抑制剂 。
制备与合成方法
生产方法
2-萘酚与苯胺在苯胺盐酸盐的催化下，于250℃进行缩合而得。将2-萘酚与苯加入缩合锅内熔化，投入苯胺盐酸盐进行缩合。反应结束后，用碳酸钠中和。蒸出过量的苯胺，再在真空下脱水干燥，经切片、打粉、包装即得防老剂丁。原料消耗(kg/t)2-萘酚（98.5%) 660苯胺（99.2%) 425