HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
N-Methyl-anilin
MONOMETHYLANILINE · Methylphenylamine · N-Methylaniline (NMA) · ANILINOMETHANE · N-MONOMETHYLANILINE · N-Methylbenzenamine · N-Methylphenylamine · N-Phenylmethylamine
Identifikatoren & physikalische Daten
| CAS No. | 100-61-8 |
|---|---|
| Summenformel | C7H9N |
| Durchschnittliche Molmasse | 107,15 g/mol |
| Monoisotopische Masse | 107,07349929 g/mol |
| SMILES | CNc1ccccc1 |
| InChIKey | AFBPFSWMIHJQDM-UHFFFAOYSA-N |
| PubChem CID | 7515 |
| ChEMBL | CHEMBL170781 |
| ChEBI | CHEBI:15733 |
| EC No. | 202-870-9 |
| DTXSID | DTXSID9021841 |
| Lokaler Name | N-Methyl-anilin |
Chemische & physikalische Eigenschaften
| XLogP | 1,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 12 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 55,4 |
| Stoffklassen | Nitrogen Compounds -> Amines, AromaticFlammable agents - 2nd degreeDye |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | Log kow = 1.661.7 |
| Geruch | Weak, ammonia-like odor. |
| Dichte | 0.989 at 68 °F (USCG, 1999) - Less dense than waterwill float0.989 @ 20 °C/4 °CRelative density (water = 1): 0.990.99 @ 20°C0.989 g/mL at 25 °C (lit.) |
| Viscosity | 2.568 cP @ 15 °C1.766 cP @ 30 °C |
| Color/Form | COLORLESS OR SLIGHTLY YELLOW LIQYellow to light brown liquid. |
| Löslichkeit | 1 to 5 mg/mL at 70.7 °F (NTP, 1992)SOL IN ETHANOL, ETHER, CARBON TETRACHLORIDE5624 mg/l @ 25 °CSolubility in water: noneInsolublewater: slightly soluble30g/L30 g/L |
| Flammpunkt | 175 °F (NTP, 1992)175 °F CC79.5 °C c.c.174 °F |
| Siedepunkt | 385.3 °F at 760 mmHg (NTP, 1992)196.25 °C194-196 °C196.2 °C @760 [mm Hg]384 °F196 °C (lit.) |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES OF /NITROGEN OXIDES/. |
| Schmelzpunkt | -71 °F (NTP, 1992)-57 °C-57 °C (lit.) |
| Dampfdruck | 0.5 hPa (20 °C) |
| Brechungsindex | n20/D 1.571(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 4.84(at 25℃) |
| Farbe | Clear yellow to brown |
| pH | 7.6 (1g/l, H2O, 20℃) |
| Geruch | Moderate aniline-type. |
| Spezifische Wärmekapazität | Cp(liquid): 1.93 J/(g·K), at 25℃ |
| Merck | 14,6019 |
| BRN | 741982 |
| Henry-Konstante | (x 10-5 atmm3/mol): 1.19 at 25 °C (approximate - calculated from water solubility and vapor pressure) |
| Dielektrizitätskonstante | 6.0(22℃) |
| Stabilität | Incompatible with strong oxidizing agents. Discolours upon exposure to air. |
| InChI | 1S/C7H9N/c1-8-7-5-3-2-4-6-7/h2-6,8H,1H3 |
| InChIKey | AFBPFSWMIHJQDM-UHFFFAOYSA-N |
| SMILES | CNc1ccccc1 |
| LogP (Verteilungskoeffizient) | 1.66 at 20℃ |
| CAS Datenbank | 100-61-8(CAS DataBase Reference) |
| NIST chemische Informationen | Aniline, N-methyl-(100-61-8) |
| EPA chemische Informationen | N-Methylaniline (100-61-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P337+P317, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Benzenamine, N-methyl-Benzenamine, N-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, N-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 28-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12653Methylaniline: Does not have an individual approval but may be used under an appropriate group standardThe 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 | Special Hazards of Combustion Products: Toxic vapors are generated when heated. (USCG, 1999)· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 79.5 °C explosive vapour/air mixtures may be formed. |
| Gesundheitsgefahren | Inhalation causes dizziness and headache. Ingestion causes blush discoloration (cyanosis) of lips, ear lobes, and fingernail beds. Liquid irritates eyes. Absorption through skin produces same symptoms as for ingestion. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Gefahrenübersicht | Methemoglobinemia and liver injury occur in animals exposed to high concentrations over a period of weeks and months. There are no reports of human poisoning by monomethyl aniline. Listed in table of Industrial Chemicals for Which Methemoglobin Formation is the Principal Cause of Toxicity[ACGIH] Can induce methemoglobinemia[ICSC] |
| DOT-Nummer und Handbuch | 2294 153 |
| Reaktive Gruppe | Amines, Aromatic |
| EG-Einstufung | Symbol: T, NR: 23/24/25-33-50/53S: (1/2)-28-36/37-45-60-61 |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: III |
| OSHA Standards | Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 2 ppm (9 mg/cu m). Skin Designation.Vacated 1989 OSHA PEL TWA 0.5 ppm (2 mg/cu m), skin designation, is still enforced in some states. |
| Reactivity Profile | N-METHYLANILINE is an aryl an amine. 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 is generated in combination with strong reducing agents, such as hydrides. |
| Chemical Dangers | Decomposes on heating and on burning. This produces toxic fumes including nitrogen oxides and aniline. Reacts violently with strong acids and oxidants. |
| Brandbekämpfung | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Use water spray, powder, foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .Rinse with plenty of water for several minutes (remove contact lenses if easily possible).Rinse mouth. Give a slurry of activated charcoal in water to drink. 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 strong oxidants, strong acids and food and feedstuffs. Keep in a well-ventilated room. Store in an area without drain or sewer access. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]0.5 [ppm] |
| Lagerbedingungen | IN GENERAL, MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, & SHOULD BE PERIODICALLY INSPECTED... INCOMPATIBLE MATERIALS SHOULD BE ISOLATED FROM EACH OTHER. |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Entsorgungsverfahren | 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. |
| Verschüttetes entsorgen | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.The worker should immediately wash the skin when it becomes contaminated.Work clothing that becomes wet or significantly contaminated should be removed and replaced. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Immediate precautionary measure |
| Wechselwirkungen | MONOMETHYL ANILINE (1.95 G/KG OF FOOD) & SODIUM NITRITE (1.0 G/L WATER) FED TO MICE CAUSED LUNG ADENOMAS & MALIGNANT LYMPHOMAS. |
| Zielorgane | respiratory system, liver, kidneys, blood, central nervous system |
| Umweltverhalten | TERRESTRIAL FATE: N-Methylaniline has low adsorptivity to soil(2) and if released on soil may leach, especially in sandy soil. It may photodegrade on the soil surface(3). Some N-methylaniline may also volatilize from the soil surface. When N-methylaniline was applied to land in sludge and the sludge allowed to dry and then tilled into the soil to a depth 6 inches within 5 days, N-methylaniline degraded fairly rapidly(1). The avg concn of N-methylaniline over 3 plots in 0-6 inch cores was 511, 138, and 16 ppb, 5, 122 and 241 days after sludge application, respectively. While 82 ppb of N-methylaniline was found in 9-15 inch cores, 5 days after application, none was found at later sampling dates. While N-methylaniline biodegrades in screening studies and may therefore be expected to biodegrade in soil, it is also known to slowly react with humic material in soil(4). It is easily oxidized(5) and may react with natural oxidants in soil(SRC).AQUATIC FATE: The Henry's Law constant is estimated to be 1.14X10-5 atm-cu m/mol(SRC), from its vapor pressure, 0.453 mm Hg(1), and water solubility, 5624 mg/L(2). Using this Henry's Law constant, its half-life in a model river and model lake is estimated to be 3.5 and 28 days, respectively(3,SRC). N-Methylaniline is sensitive to photooxidation and may photodegrade in surface water(4). It is sensitive to oxidation(5) and may be oxidized by naturally-occurring oxidants in the water body(SRC). N-Methylaniline has a low Koc(6) and BCF(7) would not be expected to adsorb to sediment or bioconcentrate in fish(SRC).ATMOSPHERIC FATE: According to its vapor pressure, 0.453 mm Hg at 25 °C(2), N-methylaniline should exist in the atmosphere as a vapor(4). It will react with photochemically-produced hydroxyl radicals with an estimated half-life of 8.8 hr(3,SRC). It may also photolyze or oxidize while in the vapor phase or in aerosols. The rates of vapor phase photolysis are unknown. N-Methylaniline is fairly soluble in water, 5624 mg/L(1), and therefore should be scavenged by rain(SRC). |
| Lebensmitteluntersuchungswerte | Samples of fresh vegetables containing N-methylaniline include (vegetable, concn): spinach, 3.4 ppmred cabbage, 0.3 ppmcarrots, 0.8 ppmcelery, 0.5 ppm(1). No N-methylaniline was found in cabbage, cauliflower, kale, white beet, swede, red beet, large radish and red radish(1). Samples of pickled vegetables containing N-methylaniline include (vegetable, concn): paprika, 13.1 ppmcucumber, 13.8 ppmcucumber with mustard, 6.1 ppmonion, 6.8 ppmcelery, 7 ppm(1). Tilsiter cheese and brown bread contained 37.9 and 0.7 ppm of N-methylaniline, but the chemical was not found in various forms of herring, cod roe and camembert and limburger cheese(1). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour, by inhalation of its aerosol, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Plant Concentrations | N-Methylaniline was detected, but not quantified in cold-pressed Valencia orange oil from Florida(1). |
| Signs and Symptoms | Blue lips, fingernails and skin. Cough. Dizziness. Headache. Laboured breathing. Sore throat.MAY BE ABSORBED! Further see Inhalation.Abdominal pain. Blue lips, fingernails and skin. Dizziness. Headache. Laboured breathing. Nausea.lassitude (weakness, exhaustion), dizziness, headachedyspnea (breathing difficulty), cyanosismethemoglobinemiapulmonary edemaliver, kidney damage |
| Effluent Concentrations | In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, N-methylaniline was identified in discharges of the following industrial category (positive occurrences, median concn in ppb): petroleum refining (1161.3), printing and publishing (19.8), pharmaceuticals (21022), foundries (12.2), aluminum (16.1), organic chemicals (518.5), publicly owned treatment works (239.8)(1). The highest effluent concn was 1736 ppb in the pharmaceuticals industry(1). N-Methylaniline was detected in the effluent of one of three New Jersey publicly-owned treatment works (POTWs) at 13-17 ppb(2). It was detected, but not quantified, in wastewater from the Kashima petrochemical complex (includes organic chemicals factory) in Japan(3). Sludge from the Muskegon County (MI) Wastewater Treatment System contained 310 ppb of N-methylaniline which was applied to land(4). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | Since the pKa of N-methylaniline is 4.848(2), N-methylaniline will be partially ionized at acidic environmental pHs and its adsorption to soil would be expected to be pH-dependent(SRC). The Koc for N-methylaniline predicted from molecular structure is 65(3). According to a suggested classification scheme(5), this estimated Koc suggests that N- methylaniline will be highly mobile in soil(SRC). Batch equilibrium studies used to determine the adsorption isotherms for N-methylaniline to a Podzol (4.85% OC pH 2.8), an Alfisol (1.25% OC, pH 6.7) and a sediment (1.58% OC, pH 7.1) yielded the results (soil, Freundlich adsorption constants (Kf), Freundlich exponent (1/n), Koc): Podzol, 22.29, 0.89, 460Alfisol, 0.59, 0.78, 47Sediment, 1.12, 0.77, 71(1). N-Methylaniline will be almost completely ionized at the pH of the Podzol and therefore ionic interactions may be dominant(1,SRC). N-Methylaniline reacts slowly with humates possibly by adding to quinoidal structures in the humic substances(4). Covalent bond formation is inferred by the lack of extractability of the aniline from the humic material as well as reactions with model compounds(4). |
| Natural Pollution Sources | N-Methylaniline is produced in nature, being found in fresh vegetables, such as spinach, red cabbage, carrots, and celery(1), and fruits, such as orange rind(2). |
| F | 8 |
| Berufliche Expositionsstufe (OEB) | B |
| Arbeitsplatzgrenzwert (OEL) | TWA: 0.5 ppm (2 mg/m3) [skin] |
| Wassergefährdungsklasse (WGK) | 3 |
| Sofort lebensgefährliche Konzentration | 100 ppm |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2294 |
| Zollcode | 29214200 |
| RTECS-Nr. | BY4550000 |
| R-Sätze (R) | 23/24/25-33-50/53 |
| Toxizität | LD in rabbits (g/kg): 0.28 orallyin rabbits, cats (mg/kg): 24, 24 i.v. (Treon) |
| Gefahrensymbole | T,N |
| Sicherheitshinweise (S) | 28-36/37-45-60-61-28A |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2STOT RE 2 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 100-61-8(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 500 °C |
Anwendungen & Verwendung
Verwenden
N-Methylaniline is used as a solvent and in organic synthesis. It is used in the production of cationic brilliant red FG, cationic pink B, reactive yellow brown KGR, etc. in the dye industry. N-methylaniline is an intermediate in the synthesis of the insecticide buprofezin and the herbicide mefenacet.
Verwenden
N-methylaniline was used as raw material, and metal-organic skeleton material CAU-10pydc was used as catalyst to catalyze the reaction of CO2 with n-methylaniline to produce N-methyl-N-phenylformamide in mild conditions and green solvent acetonitrile[1]. Poly (N-methylaniline) (PNMA) was prepared by the electrooxidation of N-methylaniline in acidic aqueous solution. PNMA prepared in acidic aqueous solution with different organic solvents and anions had different conductivity. Such as the experimental group added acetonitrile, N, N-dimethylformamide and dimethylsulfoxide, and the experimental group which adding dimethylsulfoxide had the strongest conductivity[2].References:[1] Zhiqiang Wang, Chenghua Deng, Xiao Liu, Wenmin Wang, Highly efficient conversion of CO2 into N-formamides catalyzed by a noble-metal-free aluminum-based MOF under mild conditions, 2023, 52, 11163-11167.[2] Jun YANO , Hiroko YOSHIKAWA , Tomomi MUKAI , Sumio YAMASAKI , Akira KITANI, Effect of Anions and Added Organic Solvents of Polymerizing Solutions on the Conductivity of Poly (N-methylaniline), 2006, 74, 42-48.
Herstellung & Synthese
synthetische
N-methylaniline was synthesized by the reaction of aniline with dimethyl sulfate. Dimethyl sulfate was added dropwise to the mixed solution of aniline and water below 10°C, stirred for 1 h, and then added dropwise with 30% sodium hydroxide solution. The upper layer is the organic phase, and the lower layer is extracted with benzene. After the benzene is recovered from the extract, the obtained oil Chemicalbook-like substance is combined with the organic phase to obtain a mixture of aniline, N-methylaniline and N,N-dimethylaniline. The mixture was treated with sulfuric acid, and the aniline formed sulfate crystals which were filtered off. N,N-dimethylaniline can be converted to N-methylaniline by the following reaction.