N-ethyl-3-methylaniline

HCID 7603

Basic information

CAS
102-27-2
Standard SMILES
CCNc1cccc(C)c1
InChIKey
GUYMMHOQXYZMJQ-UHFFFAOYSA-N
Molecular formula
C9H13N
Average molar mass
135.21 g/mol
Monoisotopic mass
135.10479942

Overview

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.

Names & identifiers

Preferred name
N-ethyl-3-methylaniline
IUPAC
N-ethyl-3-methylaniline
English name
N-Ethyl-3-methylaniline
Molecular formula
C9H13N
Molecular weight
135.21

Names & synonyms

N-Ethyl-m-toluidine102-27-2N-ETHYL-3-METHYLANILINEBenzenamine, N-ethyl-3-methyl-m-Toluidine, N-ethyl-m-Methyl-N-ethylanilineN-Ethyl-3-methylbenzenamineToluene, 3-(ethylamino)-NSC 8624DTXSID4021848HSDB 5347EINECS 203-019-4
Show more names
N-Ethyl-meta-toluidineN-Ethyltoluidinen-ethyl-m-toluidinN-ETHYL-3-TOLUIDINE3-ETHYLAMINOTOLUENE3(ethylamino)-toluen
BRN 074217012K193MTCRNSC-8624DTXCID1018483-METHYL-N-ETHYLANILINE4-12-00-01816 (Beilstein Handbook Reference)N-ETHYL(3-METHYLPHENYL)AMINEN-ETHYL-3-METHYLANILINE [HSDB]

Database identifiers

CAS
102-27-2
PubChem CID
7603
DTXSID
DTXSID4021848
ChEMBL
CHEMBL3182610
UNII
12K193MTCR
EC Number
203-019-4
Nikkaji
J47.802D

Properties

Computed structural properties

XLogP
3
Topological polar surface area
12 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
SpringerMaterials PropertiesOptical coefficient
Color/Form · 2 items

Light-amber liquid

Yellow liquid

SolubilitySol in ethanol and ethyl ether
Boiling Point221 °C
Vapor Pressure0.13 [mmHg]

Physicochemical properties

Melting point
-6.87 °C · -6.87°C (estimate)
Boiling point
221 °C · 221 °C (lit.)
Density
0.957 g/mL · 0.957 g/mL at 25 °C (lit.)
vapor pressure
10.9 · 10.9-106Pa at 20-50℃
refractive index
20 · n20/D 1.546(lit.)
Flash point
89 °C · 89 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

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]

Hazard information

Regulatory InformationStatus: Active Update: 17-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24872
DOT LabelPoison
Fire HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Health HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Hazards Summary · 1 item

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.

Reactive GroupAmines, Aromatic

Safety & protection

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
First AidExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 1 item

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 EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Personal Protective Equipment (PPE)Excerpt 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 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).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Soil Adsorption/Mobility · 1 item

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 · 1 item

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.

Artificial Pollution SourcesN-Ethyl-3-methylaniline's production and use in the manufacture of dyes and photographic chemicals(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

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.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
CY0440000
ridadr
UN 2754 (N-ETHYLTOLUIDINES)
hs_code
29214300

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as a dye and photographic intermediate; [HSDB]

Dye and photographic chemical intermediate

U.S. Imports(1983) 7.79X10+6 g
Methods of Manufacturingm-Toluidine + ethanol (amine formation; coproduced with N,N-diethyl-m-toluidine)
Formulations/PreparationsLiquid, technical grades
General Manufacturing InformationBenzenamine, N-ethyl-3-methyl-: ACTIVE

Applications

UsesChemical intermediate.

General DescriptionA light amber liquid. Flash point 193°F. Less dense than water and insoluble in water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make other chemicals.

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [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]
上海莉凯化工技术有限公司16628776521 · [email protected]

Related reactions

611 records

Compound notes

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