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2-Naphthylamin
naphthalen-2-amine · 2-AMINONAPHTHALENE · 2-Naphthalenamine · BETA-NAPHTHYLAMINE · 2-Naphthylamin · 2-Naphtylamine · B-NAPHTHYLAMINE · β-Naphthylamine
Identifikatoren & physikalische Daten
| CAS No. | 91-59-8 |
|---|---|
| Summenformel | C10H9N |
| Durchschnittliche Molmasse | 143,18 g/mol |
| Monoisotopische Masse | 143,07349929 g/mol |
| SMILES | Nc1ccc2ccccc2c1 |
| InChIKey | JBIJLHTVPXGSAM-UHFFFAOYSA-N |
| PubChem CID | 7057 |
| ChEMBL | CHEMBL278164 |
| ChEBI | CHEBI:27878 |
| EC No. | 202-080-4 |
| DTXSID | DTXSID2020921 |
| Lokaler Name | 2-Naphthylamin |
Chemische & physikalische Eigenschaften
| XLogP | 2,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 26 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 133 |
| Stoffklassen | Nitrogen Compounds -> NaphthylaminesCarcinogens |
| pH | WEAK BASE |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | log Kow =2.282.4 |
| Geruch | Faint aromatic odor |
| Dichte | 1.061 at 208 °F (NTP, 1992) - Denser than waterwill sink1.061 @ 98 °C/4 °C1.061 g/cm³1.06 at 208 °F1.65 @ 98°C(208 °F): 1.061.061 g/mL at 25 °C(lit.) |
| Color/Form | COLORLESS CRYSTALS WHICH DARKEN IN AIR TO A REDDISH-PURPLE COLORWhite to red crystalls [Note: Darkens in air to reddish-purple color]. |
| Löslichkeit | less than 1 mg/mL at 72 °F (NTP, 1992)Soluble in alcohol, etherSOL IN MANY ORG SOLVENTSIn water, 6.40 mg/L @ 18 °C0.189 mg/mL at 25 °CSolubility in water: poorSolubility Soluble in hot water, ethanol, ether<0.1 g/100 mL at 22 ºC |
| Corrosivity | NOT CORROSIVE |
| Flammpunkt | 315 °F (NIOSH, 2024)157 °C |
| Siedepunkt | 583 °F at 760 mmHg (NTP, 1992)306 °C, also stated as 294 °C306.2 °C @760 [mm Hg]306 °C(lit.) |
| Schmelzpunkt | 232 to 235 °F (NTP, 1992)111-113 °CMP: 109.5 °C /Technical/110.2-113 °C232 °F111-113 °C(lit.) |
| Dampfdruck | 2.56 x 10-4 mmHg at 20–30 °C (quoted, Mercer et al., 1990) |
| Brechungsindex | 1.5000 (estimate) |
| Lagerbedingungen | -20°C Freezer |
| pKa (Säurekonstante) | 4.16(at 25℃) |
| Aggregatzustand | powder |
| Farbe | pink to purple |
| Merck | 13,6425 |
| BRN | 3939429 |
| Henry-Konstante | 2.01 x 10-9 atmm3/mol at 25 °C (quoted, Mercer et al., 1990) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | Microelectronics, power transmission & fluid, insulators for electronic devices, photoresists, display device, imaging process, semiconductors, diesel fuel additives, battery, adhesive, paints, inks, chalk, leather, textiles, dye synthesis, soil products |
| InChIKey | JBIJLHTVPXGSAM-UHFFFAOYSA-N |
| CAS Datenbank | 91-59-8(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Naphthalenamine(91-59-8) |
| EPA chemische Informationen | 2-Naphthalenamine (91-59-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Hazard Traits - CarcinogenicityRestricted substance: 2-naphthylamine2-Naphthalenamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | It is combustible and at elevated temperatures evolves a vapor which is flammable ... Fire hazard: moderate, when exposed to heat or flame. |
| Gesundheitsgefahren | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Gefahrenübersicht | A bladder carcinogen regulated by OSHAsee 29 CFR 1910.1003Listed in the table Examples of Industrial Chemicals for Which Methemoglobin Formation is NOT the Principal Cause of Toxicity[ACGIH] See alpha-Naphthylamine. |
| DOT-Nummer und Handbuch | 1650 1533411 153 |
| Reaktive Gruppe | Amines, Aromatic |
| EG-Einstufung | Symbol: T, NR: 45-22-51/53S: 53-45-61Note: E |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 2-Naphthylamine (91-59-8) is listed as known to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s117naph.pdf] |
| RCRA-Anforderungen | U168As stipulated in 40 CFR 261.33, when beta-naphthylamine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| Brandbekämpfung | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Use water spray, dry powder, foam. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | 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.General First Aid:(General first aid procedures) |
| Sichere Lagerung | Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources./Use:/ Dry powder, foam, water spray. |
| Lagerbedingungen | Separated from food and feedstuffs. Well closed.Keep well closed and protected from light. /2-Naphthylamine acetate/PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/ |
| Reinigungsverfahren | Sweep spilled substance into covered containers. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment.PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/ |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Entsorgungsverfahren | [40 CFR 240-280, 300-306, 702-799 (7/1/2004)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U168, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A) Dissolve in such combustible solvent as alcohols, benzene, etc. Spray the soln into a furnace with afterburner and scrubber. B) Pour into a mixture of sand and soda ash (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in a furnace. Recommendable method: Incineration.PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/For more Disposal Methods (Complete) data for 2-NAPHTHYLAMINE (8 total), please visit the HSDB record page. |
| Verschüttetes entsorgen | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Cancer Sites | [bladder cancer] |
| Wechselwirkungen | Pentachlorophenol, a known inhibitor of hepatic sulfotransferases, caused a 2-3 fold increased in urinary levels of n-hydroxy-2-naphthylamine and its glucuronide conjugate from 2-naphthylamine treated rats. |
| Zielorgane | Bladder, skin |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1,000(2), indicates that 2-naphthylamine is expected to have low mobility in soil(SRC). Results of a batch equilibrium study with various soils indicated that 1-naphthylamine, which is structurally analogous to 2-naphthylamine, binds to soil in two phases with an initial rapid and reversible equilibrium established between the amine and the inorganic and organic components of soil followed subsequently by a strong association with the humic fraction of soil via covalent binding(3,4). Volatilization of 2-naphthylamine from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 8.10X10-8 atm-cu m/mole(5). 2-Naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.56X10-4 mm Hg(6). Based on primary soil biodegradation and mineralization studies, 2-naphthylamine is expected to biodegrade slowly in soil(7,8).AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1,000(2), indicates that 2-naphthylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 8.10X10-8 atm-cu m/mole(4). The pKa of 2-naphthylamine is 4.16(5), indicating that this compound will partially exist as a cation in the environment. According to a classification scheme(6), an estimated BCF of 11(SRC), from a log Kow of 2.28(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on primary soil biodegradation and mineralization studies, 2-naphthylamine is expected to biodegrade slowly in water(9,10).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-naphthylamine, which has a vapor pressure of 2.56X10-4 mm Hg at 25 deg(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-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 1.9 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Naphthylamine was shown to photolyze in direct sunlight with half-lives ranging from 0.05 to 0.19 hours(4). |
| Unerwünschte Wirkungen | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Expositionspfade | The substance can be absorbed into the body by inhalation, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Signs and Symptoms | Blue lips, fingernails and skin. Confusion. Dizziness. Convulsions. Headache. Nausea. Unconsciousness.MAY BE ABSORBED! Redness. Further see Inhalation.dermatitishemorrhagic cystitisdyspnea (breathing difficulty)ataxiamethemoglobinemia, hematuria (blood in the urine)dysuria[potential occupational carcinogen] |
| Effluent Concentrations | 2-Naphthylamine was detected in aqueous industrial effluent extracts collected between Nov 1979-81 at a concentration of 9150 ng/ul(1). 2-Naphthylamine was identified at a concentration of 43.6 mg/g in a basic fraction sample of HYGAS low-temperature reactor tar from a HYGAS coal gasification plant in Chicago(2). 2-Naphthylamine was found in the waste streams of the Sumida River, Japan where it has been produced and used and has been reported to be present in the effluent from certain dyestuffs factories(3). |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. |
| Medical Surveillance | Preplacement and periodic examinations should include an evaluation of exposure to other carcinogens, use of alcohol, smoking, medications, and family history. The general health of exposed persons should also be evaluated in periodic examinations.Monthly urinalysis of exposed personnel, prostatic alkaline phosphatase (PAP) examinations every 6 months, and cystoscopy should be employed where indicated.The urine cytology surveillance was found to be useful for two reasons: first, it detected tumors in 5 out of 6 cases surveyed, and second, 4 cases screened had tumors curable by transurethral operation, while other cases underwent cystectomy.PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/ |
| Soil Adsorption/Mobility | The measured Koc for 2-naphthylamine is 1,000(1). According to a classification scheme(2), this Koc value suggests that 2-naphthylamine is expected to have low mobility in soil. Results of a batch equilibrium study with various soils indicated that 1-naphthylamine, which is structurally analogous to 2-naphthylamine, binds to soil in two phases with an initial rapid and reversible equilibrium established between the amine and the inorganic and organic components of soil followed subsequently by a strong association with the humic fraction of soil via covalent binding(3,4). Aminonaphthalenes are known to form complexes with soil matter(5). The pKa of 2-naphthylamine is 4.16(6), indicating that this compound will partially exist in cation form in the environment. |
| Natural Pollution Sources | 2-Naphthylamine is not reported to occur naturally in the environment(1). |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 3411 6.1/PG II/III (beta-NAPHTHYLAMINE SOLUTION) |
| Zollcode | 29214500 |
| RTECS-Nr. | QM2100000 |
| R-Sätze (R) | 45-22-51/53 |
| Toxizität | LD50 (intraperitoneal) for mice 200 mg/kg (quoted, RTECS, 1985). |
| Gefahrensymbole | T,N |
| Sicherheitshinweise (S) | 53-45-61 |
| Gefahrenklasse | 6.1(a) |
| Verpackungsgruppe | II |
| Gefahrstoffdaten | 91-59-8(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Das 2-Naphthylamin bildet braune, glänzende, geruchlose, in Wasser unlösliche Blättchen. Es dient zur Darstellung von den farbstofftechnisch wichtigen Naphthylaminsulfonsäuren und Naphthol AS-SW. Die Produktion von Azofarbstoffen auf Basis von 2-Naphthylamin ist aber aufgrund der krebserregenden Wirkung in den letzten Jahren stark rückläufig.
Verwenden
2-Naphthylamine was widely used in themanufacture of dyes and in rubber. Currently, its use is curtailed because of thehealth hazard.