2-Ethylaniline

HCID 11357CAS 578-54-1

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

2-ETHYLANILINE578-54-1o-EthylanilineBenzenamine, 2-ethyl-o-Aminoethylbenzene2-EthylbenzenamineAniline, o-ethyl-Aniline, 2-ethyl-2-Ethyl aniline2-EthylphenylamineDTXSID0042242GR557N47K6
Show more names
NOEOLEYLETHANOLAMIDEo-ethyl-anilinAKOS 911382-ethyl-anilin
NSC-62014DTXCID8022242RefChem:86941209-424-22-ethyl-anilineNSC 62014MFCD000077512-?Ethylaniline

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

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Amines, Aromatic

Flammable agents - 2nd degree

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogPlog Kow= 1.74
Density0.982 @ 20 °C
Viscosity6.0242X10-2 Pa.s @ -46.5 °C
Color/FormBrown liquid

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.)

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 5 items

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.)

DOT LabelPoison
Fire Hazards · 2 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Fire PotentialFlammable when exposed to heat or flame ...
Health Hazards · 2 items

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 · 1 item

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.

Safety & protection

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Accidental Release Measures · 2 items

· 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 · 2 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresTo fight fire, use foam, carbon dioxide, dry chemical.
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Toxicology

Environmental Fate · 3 items

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).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Soil Adsorption/Mobility · 1 item

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).

Human Toxicity ExcerptsTOXIC BY INGESTION, INHALATION, SKIN ABSORPTION.
Artificial Pollution Sources2-Ethylaniline's production and use in the manufacturing of pharmaceuticals, dyestuffs, and pesticides(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

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.

Safety data

F
8
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
BX9800000
ridadr
UN 2273

Chemistry & industry

Pharmacology

Metabolism/Metabolites2-ethylaniline has known human metabolites that include 2-Ethylacetanilide.

Uses & manufacturing

Uses · 2 items

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.

U.S. Production2023: <50,000 lb
Industry UsesDye
General Manufacturing Information · 2 items

Synthetic Dye and Pigment Manufacturing

Benzenamine, 2-ethyl-: ACTIVE

Applications · 4 items

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.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

Related reactions

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