HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2,5-Xylidin
2,5-XYLIDINE · P-XYLIDINE · 2,5-Dimethylbenzenamine · Benzenamine, 2,5-dimethyl- · ai3-16559 · AKOS 91126 · para-xylidine · 2-amino-p-xylene
Identifikatoren & physikalische Daten
| CAS No. | 95-78-3 |
|---|---|
| Summenformel | C8H11N |
| Durchschnittliche Molmasse | 121,18 g/mol |
| Monoisotopische Masse | 121,08914935 g/mol |
| SMILES | Cc1ccc(C)c(N)c1 |
| InChIKey | VOWZNBNDMFLQGM-UHFFFAOYSA-N |
| PubChem CID | 7259 |
| ChEMBL | CHEMBL249120 |
| ChEBI | CHEBI:518305 |
| EC No. | 202-451-0 |
| DTXSID | DTXSID3026306 |
| Lokaler Name | 2,5-Xylidin |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 26 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 90,6 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | log Kow = 1.83 at pH 7.4 |
| Dichte | 0.979 at 70 °F (NTP, 1992) - Less dense than waterwill float0.9790 @ 21 °C/4 °CRelative density (water = 1): 0.980.973 g/mL at 25 °C(lit.) |
| Color/Form | YELLOW LEAF FROM PETROLEUM ETHERColorless to yellow oilYellow liquid or solid |
| Löslichkeit | less than 1 mg/mL at 64 °F (NTP, 1992)Sol in ether, carbon tetrachlorideSLIGHTLY SOL IN ETHANOLSoluble in oxygenated solvents.5600 mg/l at 12 °C in waterChloroform (Slightly), Dichloromethane (Slightly), DMSO (Sparingly)<0.1 g/100 mL at 18 ºC |
| Flammpunkt | 201 °F (NTP, 1992)93 °C |
| Siedepunkt | 417 °F at 760 mmHg (NTP, 1992)214 °C @ 760 MM HG218 °C218 °C(lit.) |
| Decomposition | When heated to decomp, xylidines emit highly toxic fumes. /Xylidines/ |
| Schmelzpunkt | 59.9 °F (NTP, 1992)15.5 °C11.5 °C(lit.) |
| Dampfdichte | 4.18 (NTP, 1992) - Heavier than airwill sink (Relative to Air)Relative vapor density (air = 1): 4.19 |
| Geruchsschwelle | Odor threshold in air= 1.00X10+12 molecules/cc. /Xylidine/Threshold for xylidine is 0.0240 mg/cu m /Xylidine/ |
| Dampfdruck | 20Pa |
| Brechungsindex | n20/D 1.559(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | pK1:4.53(+1) (25°C) |
| Farbe | Clear yellow to red-brown |
| Merck | 14,10084 |
| BRN | 2205178 |
| Henry-Konstante | 2.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| InChI | 1S/C8H11N/c1-6-3-4-7(2)8(9)5-6/h3-5H,9H2,1-2H3 |
| InChIKey | VOWZNBNDMFLQGM-UHFFFAOYSA-N |
| SMILES | Cc1ccc(C)c(N)c1 |
| LogP (Verteilungskoeffizient) | 1.83 |
| CAS Datenbank | 95-78-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzenamine, 2,5-dimethyl-(95-78-3) |
| EPA chemische Informationen | 2,5-Dimethylaniline (95-78-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301+H311+H331 (37.6%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]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)Aggregated GHS information provided per 101 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: Benzenamine, 2,5-dimethyl-Status: Active Update: 24-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/108612,5-Dimethylaniline: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Xylidines: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 93 °C explosive vapour/air mixtures may be formed. |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include headaches, drowsiness, cyanosis, mental confusion, anorexia, convulsions, nervous system and blood effects, fatigue, loss of appetite, dizziness and damage to the lungs, liver and kidneys. |
| Gefahrenübersicht | The major hazards encountered in the use and handling of 2,5-xylidine stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this colorless to yellow oil or leaf may occur from its use as a chemical intermediate for the production of dyes. Contact with 2,5-xylidine may cause burns to the skin and eyes. Death is also a possible outcome from exposure. While the OSHA PEL is set at a TWA of 5 ppm, the ACGIH lists xylidine (mixed isomers) on its 1988-1989 Notice of Intended Changes with a proposed TLV of 0.5 ppm, and a designation of "suspected human carcinogen". In activities or situations where over-exposure may occur, wear a self-contained breathing apparatus, and full chemical protective clothing which is specifically recommended by the shipper or manufacturer to prevent skin contact with xylidine. If contact should occur, immediately flush the affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. Do not eat or smoke in xylidine work areas. While xylidine does not ignite easily, it can burn with the production of irritating or poisonous gases. Also, containers may explode violently in the heat of a fire. Fires involving xylidine may be extinguished with dry chemical, CO2, Halon, or standard foam. Water spray if used, should be applied with caution because it may cause frothing. Fight the fire from a maximum distance and dike runoff from fire control water. Xylidine should be stored away from heat, strong oxidizers, and hypochlorite bleaches. Shipping regulations and other DOT regulatory requirements should be consulted before transport. If xylidine should spill, dike far ahead, then take up with sand or other noncombustible absorbent and place into containers for later disposal. Incineration is a possible form of disposal for xylidine. Before implementing land disposal of waste 2,5-xylidine, consult with environmental regulatory agencies for guidance. |
| Reaktive Gruppe | Amines, Aromatic |
| EG-Einstufung | Symbol: T, NR: 23/24/25-33-51/53S: (1/2)-28-36/37-45-61 |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | Health and Envirommental Profile for Xylidines, March 1983, p. D-183-91. |
| OSHA Standards | Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 5 ppm (25 mg/cu m). Skin Designation. /Xylidine/Vacated 1989 OSHA PEL TWA 2 ppm (10 mg/cu m), skin designation, is still enforced in some states. /Xylidine/ |
| Reactivity Profile | 2,5-XYLIDINE ignites on contact with fuming nitric acid (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. |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, carbon dioxide, foam, powder. |
| 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. Refer for medical attention . |
| 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. |
| Sichere Lagerung | Separated from strong oxidants, acids, acid anhydrides, acid chlorides, hypochlorites, halogens and food and feedstuffs. Well closed. Store in an area without drain or sewer access. |
| Brandbekämpfungsverfahren | Use water spray, dry chemicsl, foam, or CO2. Wear full protective clothing. /Xylidines/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. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Xylidines/ |
| Reinigungsverfahren | Environmental considerations - land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Xylidines/Environmental considerations - water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Xylidines/ |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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. |
| 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.Disposal methods: incineration. A). Dissolve in such combustible solvent as alcohols, benzene, etc. Spray solvent into the 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 the furnace. /Xylidines/ |
| Verschüttetes entsorgen | Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.Non-impervious clothing which becomes contaminated with xylidine should be removed immediately and not reworn until the xylidine is removed from the clothing. /Xylidines/Eating and smoking should not be permitted in areas where liquid xylidine is handled, processed, or stored. /Xylidines/Employees who handle liquid xylidine should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Xylidines/For more Preventive Measures (Complete) data for 2,5-XYLIDINE (7 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety spectacles or eye protection in combination with breathing protection. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 240(SRC), determined from a measured log Kow of 1.83(2) and a recommended regression-derived equation(3), indicates that 2,5-xylidine will have moderate mobility in soil(SRC). However, anilines are expected to bind strongly to humus or soil organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 2,5-xylidine may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.5X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Based on limited aqueous screening study data, 2,5-xylidine may be resistant to aerobic biodegradation in soil(SRC). In the Japanese MITI test 2,5-xylidine reached 0-1% of its theoretical BOD in 4 weeks(7) and was classified as slow to biodegrade(8)both tests used an activated sludge inoculum. In contrast, an activated sludge test reported rapid biodegradation (rate of 3.6 mg COD/g-hr)(9).AQUATIC FATE: Based on a recommended classification scheme for soil(1), an estimated Koc value of 240(SRC), determined from a measured log Kow of 1.83(2) and a recommended regression-derived equation(3), indicates that 2,5-xylidine should not adsorb to suspended solids and sediment in water(SRC). However, aromatic amine groups are recognized as having a strong affinity to organic carbon, suggesting that this compound may bind strongly to suspended organic material in water(4,5). 2,5-Xylidine may volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.5X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). Estimated half-lives for a model river and model lake are 16 and 120 days, respectively(3,SRC) although adsorption to organic material may attenuate this process(SRC). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically-produced hydroxyl radicals and peroxy radicals(11)typical half-lives for peroxy and hydroxy radical reactions are on the order of 19 and 30 sunlight hours, respectively(11). According to a classification scheme(7), BCF values ranging from 1.5-3.8(8), measured in carp, suggest that bioconcentration in aquatic organisms is low(SRC). Based on limited aqueous screening study data, 2,5-xylidine may be resistant to aerobic biodegradation in water(SRC). 2,5-Xylidine reached 0-1% of its theoretical BOD in 4 weeks(8) and was classified as slow to biodegrade in the Japanese MITI test(9)both tests used an activated sludge inoculum. In contrast, an activated sludge test reported rapid biodegradation (rate of 3.6 mg COD/g-hr)(10).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,5-xylidine, which has a measured vapor pressure of 0.15 mm Hg at 20 °C(2), should exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,5-xylidine 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 about 2 hours(3,SRC). |
| Expositionspfade | The substance can be absorbed into the body in hazardous amounts by inhalation, through the skin and by ingestion. |
| Plant Concentrations | ... Has been detected in the steam distillate of cured Latakia tobacco, which is used in pipe tobacco. |
| Signs and Symptoms | Dizziness. Drowsiness. Headache. Nausea.MAY BE ABSORBED! See Ingestion.Blue lips, fingernails and skin. Dizziness. Drowsiness. Headache. Nausea. Unconsciousness. |
| ICSC Environmental Data | This substance may be hazardous to the environment. Special attention should be given to aquatic organisms. |
| Medical Surveillance | Initial medical examination: A complete history & physical examination. The purpose is to detect existing conditions that might place the exposed employee at increased risk, and to establish a baseline for future health monitoring. Exam of the blood, lungs, liver, kidneys, and cardiovascular system should be stressed. ... Periodic medical exam ... should be repeated on an annual basis. /Xylidine/ |
| Soil Adsorption/Mobility | The Koc of 2,5-xylidine is estimated as approximately 240(SRC), using a measured log Kow of 1.83(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 2,5-xylidine has moderate mobility in soil(SRC). However, anilines are expected to bind strongly to humus or soil organic matter in soils due to the high reactivity of the aromatic amino group(4,5). Low adsorption is observed at a neutral pH with pure clay minerals or soils for substituted anilines(5). |
| Artificial Pollution Sources | 2,5-Xylidine's production and use as a dye intermediate(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | 2,5-Xylidine, present at 100 mg/L, reached 0-1% of its theoretical BOD in 4 weeks using an activated sludge inoculum(1). In the Japanese MITI test, 2,5-xylidine (present at 100 mg/L) was classified as slow to biodegrade indicating that only 0-29% of the theoretical BOD was reached in 2 weeks using an activated sludge inoculum(2). 2,5-Xylidine, initially present at 200 mg/L COD, reached 96.5% degradation (measured as removal of COD) with a rate of biodegradation of 3.6 mg COD/g-hr using an activated sludge inoculum(3). |
| Carcinogen Classification | 2,5-XylidineGroup 3: Not classifiable as to its carcinogenicity to humansVolume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals1987 |
| Environmental Bioconcentration | A BCF value of 1.5-3.2 and <3.8 was measured for 2,5-xylidine at 1 and 0.1 mg/l, respectively, in carp(1). According to a classification scheme(2), these BCF values suggest that bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 2,5-xylidine is estimated as 2.5X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 2,5-xylidine will volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 16 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 120 days(2,SRC). Adsorption to organic material in water may attenuate this process(SRC). 2,5-Xylidine's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). |
| F | 8-10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1711 6.1/PG 2 |
| Zollcode | 29214910 |
| RTECS-Nr. | ZE9100000 |
| R-Sätze (R) | 23/24/25-33-51/53-48/20 |
| Gefahrensymbole | T,N,Xn |
| Sicherheitshinweise (S) | 28-36/37-45-61-28A |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2STOT RE 2 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Gefahrstoffdaten | 95-78-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
2,5-Dimethylaniline is widely used as raw materials to produce imaging chemicals like organic dyes and pigments. It is also used in the production of antioxidants, pharmaceutical, agricultural, rubber chemicals and other target organic molecules. 2,5-Dimethylaniline was also used in the synthesis of nanocomposite of multi-walled carbon nanotubes embedded in poly(2,5-dimethylaniline). 2,5-Dimethylaniline was used to study the effect of metabolites formed from 2,5-xylidine by fungi on laccase activity. The Fourier transform infrared (FTIR) and Raman spectra of 2,5-dimethylaniline was studied5. It induced transcription of lccIV.