Grundinformationen
- Standard-SMILES
CCNc1cccc(C)c1- InChIKey
GUYMMHOQXYZMJQ-UHFFFAOYSA-N- Summenformel
- C9H13N
- Durchschnittliche Molmasse
- 135,21 g/mol
- Monoisotopische Masse
- 135,10479942
Überblick
N-ethyl-m-toluidine appears as a light amber liquid. Less dense than water and insoluble in water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make other chemicals.
Namen und Bezeichner
- Bevorzugter Name
- N-ethyl-3-methylaniline
- IUPAC
- N-ethyl-3-methylaniline
- Lokaler Name
- N-Ethyl-m-toluidin
- Englischer Name
- N-Ethyl-3-methylaniline
- Summenformel
- C9H13N
- Molmasse
- 135.21
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
102-27-2- PubChem CID
- 7603
- DTXSID
DTXSID4021848- ChEMBL
CHEMBL3182610- UNII
- 12K193MTCR
- EC Number
- 203-019-4
- Nikkaji
- J47.802D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3
- Polarare Oberfläche (TPSA)
- 12 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 90,7
Experimentelle und physikochemische Eigenschaften
Color/Form
Light-amber liquid
Yellow liquid
Physical Description
N-ethyl-m-toluidine appears as a light amber liquid. Less dense than water and insoluble in water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make other chemicals.
Light amber or yellow liquid; [HSDB] Clear brownish-yellow liquid; [MSDSonline]
Physikochemische Eigenschaften
- Schmelzpunkt
- -6.87 °C · -6.87°C (estimate)
- Siedepunkt
- 221 °C · 221 °C (lit.)
- Dichte
- 0.957 g/mL · 0.957 g/mL at 25 °C (lit.)
- Dampfdruck
- 10.9 · 10.9-106Pa at 20-50℃
- Brechungsindex
- 20 · n20/D 1.546(lit.)
- Flammpunkt
- 89 °C · 89 °C
- Löslichkeit
- soluble in Alcohol,Ether
- Aggregatzustand
- clear liquid
- pka
- 5.27 · 5.27±0.25(Predicted)
- Farbe
- Colorless to Red to Green
- Wasserlöslichkeit
- 1131 mg/L · 1131 mg/L (20 ºC)
- BRN
- 742170 · 742170
- Henry's Law Constant
- 1.6 · 1.6×100 mol/(m3Pa) at 25℃, HSDB (2015)
- InChI
- 1S/C9H13N/c1-3-10-9-6-4-5-8(2)7-9/h4-7,10H,3H2,1-2H3
- InChIKey
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N
- SMILES
- CCNc1cccc(C)c1
- CAS Datenbank
- 102 · 102-27-2(CAS DataBase Reference)
- NIST chemische Informationen
- -3 · Benzenamine, N-ethyl-3-methyl-(102-27-2)
- EPA chemische Informationen
- N-Ethyl-m-toluidine (102-27-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H301+H311+H331 (43.7%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 87 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H227: Combustible liquid [Warning Flammable liquids]
Gefahrenhinweise
Hazards Summary
Emergency treatment: Aniline; [HSDB] Mildly irritating to rabbit skin and eyes; Not sensitizing to rabbit skin; Methemoglobinemia and hemolytic anemia observed in 2-week inhalation study of rats; Some evidence of mutagenicity; [EPA HPVIS] An irritant; Toxic by ingestion, inhalation, or skin absorption; [Aldrich MSDS] See Aniline.
Reactivity Profile
N-ETHYL-M-TOLUIDINE 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.
DOT Emergency Guidelines
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /N-Ethyltoluidines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /N-Ethyltoluidines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /N-Ethyltoluidines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /N-Ethyltoluidines/
For more DOT Emergency Guidelines (Complete) data for N-ETHYL-3-METHYLANILINE (8 total), please visit the HSDB record page.
Hazard Classes and Categories
Acute Tox. 3 (98.9%)
Flammable liquids - Category 4
Flammable liquids - Category 4
Hazardous to the aquatic environment (Acute) - Category 3
Shipment Methods and Regulations
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Shipping Name/ Number DOT/UN/NA/IMO
UN 2754; N-Ethyltoluidines
IMO 6.1; N-Ethyltoluidines (ortho-; meta-; para-)
Sicherheit und Schutzausrüstung
Disposal Methods
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.
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 194(SRC), determined from a structure estimation method(2), indicates that N-ethyl-3-methylaniline is expected to have moderate mobility in soil(SRC). However, aromatic amines(including anilines) bind to humate found in soil in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with humate carbonyls(3). Subsequently, there is a slow reaction that is not readily reversible(3). Also, the pKa value for N-ethyl-3-methylaniline is expected to range between 4.96 and 5.72 based on its structural similarity with N-ethyl-2-methylaniline and N-ethyl-4-methylaniline(4). This suggests that N-ethyl-3-methylaniline will exist partially in the protonated form in moist soils and the protonated form of N-ethyl-3-methylaniline is expected to bind strongly to soil surfaces(SRC). Volatilization of N-ethyl-3-methylaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). N-Ethyl-3-methylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.13 mm Hg(SRC), determined from a fragment constant method(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 194(SRC), determined from an estimation method(2), indicates that N-ethyl-3-methylaniline is not expected to adsorb to sediment and suspended solids in water(SRC). The pKa value for N-ethyl-3-methylaniline is expected to range between 4.96 and 5.72 based on its structural similarity with N-ethyl-2-methylaniline and N-ethyl-4-methylaniline(3). This pKa value suggests that N-ethyl-3-methylaniline will exist partially in the protonated form in aqueous environments and the protonated form of N-ethyl-3-methylaniline is expected to bind strongly to sediment and suspended solids in water(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 4.7 and 55 days, respectively(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humate material in the water column(6). The protonated form of N-ethyl-3-methylaniline is not expected to volatilize from water(3). According to a classification scheme(7), an estimated BCF of 22(SRC), from an estimated log Kow of 2.6(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-ethyl-3-methylaniline, which has an estimated vapor pressure of 0.13 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-ethyl-3-methylaniline 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 3.2 hrs(SRC), from its rate constant of 1.2X10-10 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for N-ethyl-3-methylaniline can be estimated to be 194(SRC). According to a classification scheme(2), this estimated Koc value suggests that N-ethyl-3-methylaniline is expected to have moderate mobility in soil. However, aromatic amines(including anilines) bind to humate found in soil in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with humate carbonyls(3). Subsequently, there is a slow reaction that is not readily reversible(3). Also, the pKa value for N-ethyl-3-methylaniline is expected to range between 4.96 and 5.72 based on its structural similarity with N-ethyl-2-methylaniline and N-ethyl-4-methylaniline(4). This suggests that N-ethyl-3-methylaniline will exist partially in the protonated form in moist soils and the protonated form of N-ethyl-3-methylaniline is expected to bind strongly to soil surfaces(SRC).
TSCA Test Submissions
N-ethyl-meta-toluidine (CAS # 102-27-2) was evaluated for acute oral toxicity in Sprague-Dawley rats (5/sex/group) fed doses of 100, 500, 750, and 1000 mg/kg once by oral gavage. Treatment was associated with mortality consistent with an oral LD50 (with 95% confidence limits) of 787 (585-1058) mg/kg. Only animals of 750 and 1000 mg/kg doses died and all, but 3 rats deceased on Days 4, 5, and 7, died on Days 2 and 3 post-gavage. All surviving rats gained weight. Clinical toxicity was characterized by cyanosis in all but 2 rats of 100 mg/kg doses and 1 of a 500 mg/kg dose. Other pharmacotoxic signs noted in more than 1 treated rat included hypoactivity, wet inguinal and/or discolored fur, discolored paws, redness about the nose, discoloration about the mouth, rough hair coat, dyspnea, diarrhea, ataxia, coldness to touch, dark urine, vocalization, pallor, and dyspnea. Necropsy of decedent rats and rats surviving 14-day post-gavage observation identified no gross pathology among animals of 100 or 500 mg/kg doses. Among rats of higher doses (750, 1000 mg/kg), gross lesions included dark brown, red, and/or mottled lungs; dark brown and/or small spleen; dark brown or pale liver; dark brown heart, red fluid-filled urinary bladder, dark brown kidney, and thymic foci.
Environmental Bioconcentration
An estimated BCF of 22 was calculated for N-ethyl-3-methylaniline(SRC), using an estimated log Kow of 2.6(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
Volatilization from Water/Soil
The Henry's Law constant for N-ethyl-3-methylaniline is estimated as 6.1X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that N-ethyl-3-methylaniline is expected to volatilize from water surfaces(2). 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)(2) is estimated as 4.7 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 55 days(SRC). N-Ethyl-3-methylaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humate material in the water column(3). N-Ethyl-3-methylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.13 mm Hg (SRC), determined from a fragment constant method(4). The pKa value for N-ethyl-3-methylaniline is expected to exist between 4.96 and 5.72 based on its structural similarity with N-ethyl-2-methylaniline and N-ethyl-4-methylaniline(5). This suggests that N-ethyl-3-methylaniline will exist partially in the protonated form in aqueous environments which is not expected to volatilize from water.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of N-ethyl-3-methylaniline with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.2 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). N-Ethyl-3-methylaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). In general, anilines absorb light in the environmental UV spectrum(>290 nm)(3). Based on this, N-ethyl-3-methylaniline is expected to absorb light and may potentially undergo direct photolysis(SRC).
Environmental Fate/Exposure Summary
N-Ethyl-3-methylaniline's production and use in the manufacture of dyes and photographic chemicals and its coproduction with N,N-diethyl-m-toluidine may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 0.13 mm Hg at 25 °C indicates N-ethyl-3-methylaniline will exist solely as a vapor phase in the ambient atmosphere. Vapor-phase N-ethyl-3-methylanilne will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 3.2 hrs. If released to soil, N-ethyl-3-methylaniline is expected to have moderate mobility based upon an estimated Koc of 194. However, aromatic amines(including anilines) bind to humate found in soil in two phases which could decrease movement in soil. Also, the pKa value for N-ethyl-3-methylaniline is expected to range between 4.96-5.72 based on its structural similarity with N-ethyl-2-methylaniline and N-ethyl-4-methylaniline. This suggests that N-ethyl-3-methylaniline will exist partially in the protonated form in moist soils and the protonated form of N-ethyl-3-methylaniline is expected to bind strongly to soil surfaces. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole. If released into water, N-ethyl-3-methylaniline is expected to slightly adsorb to sediment and suspended solids in water based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 4.7 and 55 days, respectively. However, volatilization from water surfaces may be attenuated by adsorption to humate material in the water column. The protonated form of N-ethyl-3-methylaniline in aqueous environments is not expected to volatilize from water. An estimated BCF of 22 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to occur due to the lack of hydrolyzable functional groups. Occupational exposure to N-ethyl-3-methylaniline may occur through inhalation and dermal contact with this compound at workplaces where N-ethyl-3-methylaniline is produced or used. (SRC)
Antidote and Emergency Treatment
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias as necessary... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation... . /Aniline and related compounds/
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- ridadr
- UN 2754 (N-ETHYLTOLUIDINES)
- hs_code
- 29214300
- RTECS-Nr.
- CY0440000
- risk_code
- 23/24/25-36/37/38-52/53
- hazard_code
- T
- safety_code
- 26-36/37/39-45-61-28A
- hazard_class
- 6.1
- packing_group
- II
- Speicherklasse
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Giftige Stoffe Daten
- 102-27-2(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as a dye and photographic intermediate; [HSDB]
Dye and photographic chemical intermediate
Anwendungen
VerwendenChemical intermediate.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…