Basic information
- Standard SMILES
CCc1ccccc1N- InChIKey
MLPVBIWIRCKMJV-UHFFFAOYSA-N- Molecular formula
- C8H11N
- Average molar mass
- 121.18 g/mol
- Monoisotopic mass
- 121.08914935
Overview
2-ethylaniline appears as a brown liquid. Insoluble in water and less dense than water. Hence floats on water. May irritate skin, eyes and mucous membranes. Toxic by ingestion, inhalation or skin absorption.
Names & identifiers
- Preferred name
- 2-Ethylaniline
- IUPAC
- 2-ethylaniline
- English name
- 2-Ethylaniline
- Molecular formula
- C8H11N
- Molecular weight
- 121.18
Names & synonyms
Show more names
Database identifiers
- CAS
578-54-1- PubChem CID
- 11357
- DTXSID
DTXSID0042242- ChEMBL
CHEMBL3185556- UNII
- GR557N47K6
- EC Number
- 209-424-2
- Nikkaji
- J28.429G
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 26 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 80.6
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Amines, Aromatic
Flammable agents - 2nd degree
Solubility
Soluble in alcohol and toluene; insoluble in water
Slightly soluble in chloroform and water; very soluble in ethanol and ethyl ether
Flash Point
185 °F (NFPA, 2010)
85 °C
185 °F (85 °C) (OPEN CUP)
Vapor Pressure
0.17 [mmHg]
0.170 mm Hg
Physicochemical properties
- Melting point
- -44 °C · -44 °C (lit.)
- Boiling point
- 210 °C · 210 °C (lit.)
- Density
- 0.983 g/mL · 0.983 g/mL at 25 °C (lit.)
- vapor density
- 4.2 · 4.2 (vs air)
- vapor pressure
- 0.11 mm · 0.11 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.559(lit.)
- Flash point
- 196 °F · 196 °F
- storage temp.
- 20 °C · −20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Liquid
- pka
- 1 · pK1:4.42(+1) (25°C)
- color
- Clear yellow to red-brownish
- Water Solubility
- insoluble
- BRN
- 1841268 · 1841268
- Henry's Law Constant
- 2.6 · 2.6×100 mol/(m3Pa) at 25℃, Brockbank (2013)
- InChI
- 1S/C8H11N/c1-2-7-5-3-4-6-8(7)9/h3-6H,2,9H2,1H3
- InChIKey
- MLPVBIWIRCKMJV-UHFFFAOYSA-N
- SMILES
- CCc1ccccc1N
- LogP
- 1.74 · 1.74
- CAS DataBase Reference
- 578 · 578-54-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 557 N47K6 · GR557N47K6
- NIST Chemistry Reference
- 2 · 2-Ethylaniline(578-54-1)
- EPA Substance Registry System
- o-Ethylaniline (578-54-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06,GHS09
- Signal word
- Danger
- Hazard statements
- 311 · H311+H331-H302-H315-H319-H411
- Precautionary statements
- 501 · P501-P261-P273-P270-P271-P264-P280-P391-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- T
- Risk Statements
- 36 · 36/37/38-33-23/24/25
- Safety Statements
- 36 · 36/37/39-45-36/37-28A
- RIDADR
- 2273 · UN 2273
- WGK Germany
- 3 · 3
- RTECS
- 9800000 · BX9800000
- F
- 8 · 8
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29214980 · 29214980
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationSTOT RE 2
- Hazardous Substances Data
- 578 · 578-54-1(Hazardous Substances Data)
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (58.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, 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 125 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenamine, 2-ethyl-
Benzenamine, 2-ethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 2-ethyl- 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: 20-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/17856
2-Ethylaniline: Does not have an individual approval but may be used under an appropriate group standard
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.)
Fire Hazards
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
· Combustible material: may burn but does not ignite readily.
Health Hazards
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.
Hazards Summary
Emergency treatment: Aniline; [HSDB] May cause skin, eye, and mucous membrane irritation; [CAMEO] Cyanosis observed in rats within 24 hours of dosing in lethal-dose gavage study; Not irritating to skin and mildly irritating to eyes of rabbits; [EPA: HPVIS] May cause skin, eye, mucous membrane, and upper respiratory tract irritation; Exposure to high concentrations can induce methemoglobinemia; Long-term exposure may cause changes in liver and nervous system; No evidence of mutagenicity; [NTP] Harmful if ingested; Toxic by inhalation or skin absorption; [Aldrich MSDS] See Aniline.
Reactivity Profile
2-ETHYLANILINE neutralizes acids in exothermic reactions to form salts plus water. The liquid may react with acids to release toxic fumes of aniline and oxides of nitrogen. Reacts violently with oxidizing materials. 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)/ 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.
/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.
/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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.
/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.
For more DOT Emergency Guidelines (Complete) data for 2-ETHYLANILINE (8 total), please visit the HSDB record page.
DOT Hazard Classification
2-Ethylaniline
UN2273
Div 6.1 Poisonous materials (49 eCFR § 173.132)
PG III: the degree of danger presented by the material is minor
Safety & protection
Accidental Release Measures
· 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.
First Aid
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
General First Aid:
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.
Isolation and Evacuation
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Immediate precautionary measure
Toxicology
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 143(SRC), determined from a structure estimation method(2), indicates that 2-ethylaniline is expected to have high mobility in soil(SRC). However, aromatic amines (including anilines) bind to humic material found in soil in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). Also, a pKa value of 4.3(4) suggests that 2-ethylaniline will exist partially in the protonated form in moist soils and the protonated form of 2-ethylaniline is expected to bind strongly to soil surfaces and not volatilize. Volatilization of the neutral species from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.6X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2-Ethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.170 mm Hg(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 143(SRC), determined from an estimation method(2), indicates that 2-ethylaniline is not expected to adsorb to sediment and suspended solids in water(SRC). However, aromatic amines(including anilines) bind to humic material found in water in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). Volatilization of the neutral species from water surfaces is expected(4) based upon an estimated Henry's Law constant of 3.6X10-6 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 7.5 and 85 days, respectively(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column(3). A pKa value of 4.30(6), suggests that 2-ethylaniline will exist partially in the protonated form in aqueous environments and the protonated form of 2-ethylaniline is not expected to volatilize from water. According to a classification scheme(7), an estimated BCF of 4.4(SRC), from a log Kow of 1.79(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), 2-ethylaniline, which has a vapor pressure of 0.170 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-ethylaniline 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 hrs(SRC), calculated from its rate constant of 1.3X10-10 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3).
Soil Adsorption/Mobility
A pKa value of 4.30(1) suggests that 2-ethylaniline will exist partially in the protonated form in moist soils and the protonated form of 2-ethylaniline is expected to bind strongly to soil surfaces(SRC). Using a structure estimation method based on molecular connectivity indices(2), the Koc for 2-ethylaniline can be estimated to be 143(SRC). According to a classification scheme(3), this estimated Koc value suggests that 2-ethylaniline is expected to have high mobility in soil. However, aromatic amines (including anilines) bind to humic material found in soil in two phases(4). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(4). Subsequently, there is a slow reaction that is not readily reversed(4).
Environmental Bioconcentration
An estimated BCF of 4.4 was calculated for 2-ethylaniline(SRC), using a log Kow of 1.74(1) 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 the 2-ethylaniline neutral species is estimated as 3.6X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that the neutral species 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 7.5 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 85 days(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column(3). Aromatic amines (including anilines) bind to humic material found in water in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). 2-Ethylaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2-Ethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.170 mm Hg(4). A pKa value of 4.3(5), suggests that 2-ethylanilne will exist partially in the protonated form in aqueous environments and the protonated form of 2-ethylaniline is not expected to volatilize from water or moist soil surfaces(SRC).
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 2-ethylaniline with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Ethylaniline 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, 2-ethylaniline is expected to absorb light and may potentially undergo direct photolysis(SRC).
Environmental Fate/Exposure Summary
2-Ethylaniline's production and use in the manufacturing of pharmaceuticals, dyestuffs, and pesticides may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.170 mm Hg at 25 °C indicates 2-ethylaniline will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-ethylaniline 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 hrs. If released to soil, 2-ethylaniline is expected to have high mobility based upon an estimated Koc of 143. However, aromatic amines (including anilines) bind to humic material found in soil in two phases which could decrease movement in soil. Also, a pKa value of 4.3 suggests that 2-ethylaniline will exist partially in the protonated form in moist soils and the protonated form of 2-ethylaniline is expected to bind strongly to soil surfaces and not volatilize. Volatilization of the neutral species from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 3.6X10-6 atm-cu m/mole. If released into water, 2-ethylaniline is not expected to adsorb to sediment and suspended solids in water based upon the estimated Koc. Volatilization of the neutral species 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 7.5 and 85 days, respectively. However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column. The protonated form of 2-ethylaniline is not expected to volatilize from water. An estimated BCF of 4.4 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 2-ethylaniline may occur through inhalation and dermal contact with this compound at workplaces where 2-ethylaniline 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/
Safety data
- F
- 8
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BX9800000
- ridadr
- UN 2273
- hs_code
- 29214980
- risk_code
- 36/37/38-33-23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS09
- hazard_code
- T
- safety_code
- 36/37/39-45-36/37-28A
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H311+H331-H302-H315-H319-H411
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationSTOT RE 2
- Precautionary statements
- P501-P261-P273-P270-P271-P264-P280-P391-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
- Hazardous Substances Data
- 578-54-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used as an intermediate for pharmaceuticals, dyestuffs, and pesticides; [Hawley] Also used as a reactant in conductive polymer production; [NTP]
Intermediate for pharmaceuticals, dyestuffs, pesticides, and other products.
General Manufacturing Information
Synthetic Dye and Pigment Manufacturing
Benzenamine, 2-ethyl-: ACTIVE
Applications
Description2-Ethylaniline is a yellow liquid that turnsbrown on standing in air. Molecular weight = 121.20;Boiling point = 215℃; 210℃ at 760 mmHg; Freezing/Melting point = 44℃; Vapor pressure = 0.11 mmHg at20℃; Flash point = 85℃ (oc). Hazard Identification (basedon NFPA-704 M Rating System): Health 3, Flammability 2,Reactivity 0. Insoluble in water.
UsesIntermediate for pharmaceuticals, dyestuffs, pesticides, and other products.
Uses2-Ethylaniline is a reagent in the synthesis of bromoanthraquinones with different substituents producing novel dyes. Also used in the optimization of phoephoinositide 3-kinase inhibitor which is used in the synthesis.
General DescriptionA brown liquid. Insoluble in water and less dense than water. Hence floats on water. Flash point 185°F. May irritate skin, eyes and mucous membranes. Toxic by ingestion, inhalation or skin absorption.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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