103-69-5 Hazards Identification
Pictogram(s):
Signal:
Danger
GHS Hazard Statements:
H301: Toxic if swallowed [Danger Acute toxicity, oral]
H311: Toxic in contact with skin [Danger Acute toxicity, dermal]
H331: Toxic if inhaled [Danger Acute toxicity, inhalation]
H373 **: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
Precautionary Statement Codes:
P260, P261, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P403+P233, P405, and P501
Hazard Classes and Categories:
Acute Tox. 3 *
STOT RE 2 *
Acute toxicity - category 3
Specific target organ toxicity (repeated exposure) - category 2
Hazardous to the aquatic environment (Acute) - Category 2
Hazardous to the aquatic environment (Long-term) - Category 2
Flammable liquids - Category 4
Acute toxicity (Oral) - Category 4
Acute toxicity (Dermal) - Category 5
Skin corrosion/irritation - Category 2
Serious eye damage/eye irritation - Category 2A-2B
Specific target organ toxicity - Single exposure - Category 1 (blood system)
Specific target organ toxicity - Repeated exposure - Category 1 (blood system)
Flammable - 2nd degree
Hazards Summary:
In animal feeding studies, it induces anemia and methemoglobinemia; [HSDB] Contact with substance may cause burns to skin and eyes; [CAMEO]
103-69-5 Usage
Uses
N-Ethylaniline is used in various applications across different industries due to its unique properties. Some of its primary uses include:
1. Used in Explosives Industry:
N-Ethylaniline is used as an explosive stabilizer, enhancing the safety and performance of explosives by preventing premature detonation.
2. Used in Dyestuff Manufacture:
N-Ethylaniline serves as an intermediate in the manufacturing of dyes, contributing to the production of various colorants used in the textile and other industries.
3. Used in Pharmaceutical Industry:
N-Ethylaniline is utilized as an intermediate in the synthesis of certain pharmaceuticals, playing a crucial role in the development of new drugs.
4. Used in Organic Synthesis:
N-Ethylaniline is employed in organic synthesis for the production of various organic compounds, such as 2-(N-ethylphenylamino)-1,4-benzoquinone, 2-(arylaminomethyl)phenylboronic acid, and poly(methyl methacrylate) (PMMA) films containing NEA.
5. Used in Analytical Chemistry:
N-Ethylaniline (NEA) is used as an internal standard in the gas chromatography (GC) analysis of nicotine extraction from nicotine gum, ensuring accurate and reliable results.
6. Used in the Synthesis of Conducting Polymers:
N-Ethylaniline is used in the synthesis of poly(N-ethylaniline) (PNEA), a conducting polymer with potential applications in sensors, actuators, and electronic devices.
Occurrence:
N-Ethylaniline has been reported as a contaminant in various contexts, such as in polyethylene bottles used in intravenous solutions, where it may originate from rubber parts of the closure. It has also been found in rubber containing N,N,-dithiodimorpholine accelerator of vulcanization, which can release N-ethylaniline into aqueous media. Additionally, N-Ethylaniline has been identified as a contaminant in cigarette smoke at a level of 55.8 ng per one U.S. 85 mm cigarette.
Production Methods
Manufacture of N-ethylaniline is based on the reaction of aniline with alkyl halide or by heating aniline with ethyl alcohol under acidic conditions followed by purification (Windholz et al 1983).
Synthesis Reference(s)
Journal of the American Chemical Society, 78, p. 4778, 1956 DOI: 10.1021/ja01599a063The Journal of Organic Chemistry, 21, p. 988, 1956Tetrahedron Letters, 25, p. 1635, 1984 DOI: 10.1016/S0040-4039(01)81131-X
Air & Water Reactions
Unstable to prolonged exposure to air and/or light. Insoluble in water.
Reactivity Profile
N-Ethylaniline may react violently with nitric acid. May react with strong oxidizing agents. . 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.
Hazard
Toxic by ingestion, inhalation, and skin
absorption.
Health Hazard
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.
Health Hazard
N-Ethylaniline is considered very hazardous in a fire situation, since it is highly toxic and readily absorbed by the inhalation, dermal and oral routes (HSDB 1988). Excessive exposure causes respiratory paralysis.
Fire Hazard
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. 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.
Safety Profile
Poison by ingestion and
intraperitoneal routes. Moderately toxic by
an unspecified route. Mddly toxic by skin
contact. An allergen. Flammable when
exposed to heat or flame; can react with
oxidizing materials. To fight fire, use dry
chemical, CO2, foam. Hypergolic reaction
with red fuming nitric acid. When heated to
decomposition or on contact with acid or
acid fumes it emits highly toxic fumes of
aniline and NOx.
Potential Exposure
This material is used as an intermediate in dyes, pharmaceuticals and explosives; in organic
synthesis.
Metabolism
The metabolism of N-ethylaniline has been studied more as a tool to understanding microsomal drug metabolizing activity than as the central item of inquiry. However, the following have been clearly defined as metabolic products of N-ethylaniline: phenylhydroxylamine, N-hydroxyl, N-ethylaniline; N-ethyl-p-aminophenol; and aniline (Appel et al 1965; Heinze 1970; Hlavica 1970; Hlavica and Kiese 1969; Kampffmeyer and Kiese 1965; Kroeber et al 1970; Lange 1967 and Lange 1968). Nonmicrosomal metabolism has not been reported. Species shown capable of metabolism include rabbit, mouse, rat, dog, pig, and guinea pig with the proportions of the various metabolites often species dependent. Compounds similar to N-ethylaniline such as N-methyl-N-ethylaniline can form N-ethylaniline via demethylation (Gorrod et al 1975a,b).
Shipping
UN2272 N-Ethylaniline, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials
Incompatibilities
May form explosive mixture with air.
Decomposes on contact with light or air. Reacts with many
materials. Neutralizes acids in exothermic reactions to form
salts plus water. Flammable gaseous hydrogen may be generated in combination with strong reducing agents such as hydrides, nitrides, alkali metals, and sulfides. Contact with
strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from
alkaline materials; strong acids, such as nitric acid, can
cause fire; explosions with formation of toxic vapors of
aniline and oxides of nitrogen; strong bases, isocyanates,
halogenated organics, phenols (acidic), epoxides, anhydrides, and acid halides
Check Digit Verification of cas no
The CAS Registry Mumber 103-69-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 3 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 103-69:
(5*1)+(4*0)+(3*3)+(2*6)+(1*9)=35
35 % 10 = 5
So 103-69-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N/c1-2-9-8-6-4-3-5-7-8/h3-7,9H,2H2,1H3/p+1
103-69-5Relevant academic research and scientific papers
Dub, Pavel A.,Rodriguez-Zubiri, Mireia,Baudequin, Christine,Poli, Rinaldo
, p. 1392 - 1396 (2010)
The platinum-catalyzed and halide-promoted hydroamination of ethylene with aniline is reported for the first time in the presence of simple sodium halides in water. Compounds K2PtX4 (X = Cl or Br), PtX2 or PtX4 (0.3% mol) in the presence of an aqueous solution of excess NaX and aniline under ethylene pressure (25 bar) affords N-ethylaniline with 60-85 turnovers after 10 h at 150°C. The best result (TON = 85) was obtained in the presence of excess NaBr, whereas a slightly lower activity was observed with NaCl (60 cycles) and practically no activity with NaF or NaI (2-4 cycles). The reaction also produces N,N-diethylaniline (up to 1 cycle) and 2-methylquinoline (up to 8 cycles) as by-products. The influence of added H + and different oxidizing agents was also examined.
Hajipour, Abdol R.,Dordahan, Fatemeh,Rafiee, Fatemeh,Mahdavi, Mohammad
, p. 809 - 813 (2014)
Nanometric copper oxide supported on silica has been found to be a highly efficient and reusable catalyst for the C-N cross-coupling reaction of amines with aryl halides under ligand-free conditions. Various arylamines with different substituted groups can be synthesized in moderate to good yields. The catalyst can be recycled at least five times without obvious loss in catalytic activity.
Sampath Kumar,Subba Reddy,Anjaneyulu,Yadav
, p. 8305 - 8306 (1999)
Mono-N-alkyl anilines were obtained in high yields within a short reaction time when various aromatic azides were reacted with alkyl magnesium halides at room temperature.
Makhmutov
, p. 1166 - 1172 (2018)
One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.
Kadyrov, Renat
, p. 185 - 191 (2019)
A simple and general protocol was developed for selective conversion of amides into amines. Amides were converted into amide acetals and imido esters by O-alkylation and then hydrogenated without isolation into amines under very mild reaction conditions over standard hydrogenation catalysts. Triethyloxonium tertafluoroborate, methyl trifluoromethanesulfonate, dimethyl sulfate and ethyl chloroformate were validated as alkylating agent. The synthetic utility of this approach was demonstrated by the selective carbonyl reduction of peptide groups. Carbonyl reduction of peptide group proceeds chemoselective without racemization of the neighboring chiral center. (Figure presented.).
Bethegnies, Aurelien,Dub, Pavel A.,Poli, Rinaldo
, p. 1882 - 1891 (2013)
The selectivity of the catalytic reaction between aniline and ethylene in the presence of the Brunet catalyst (PtBr2/Br-) shifts from the hydroamination product N-ethylaniline to the heterocyclization product 2-methylquinoline (quinaldine) when conducted in the presence of PPh3 (1 equiv per Pt atom). Condition optimization revealed that this process works best in the absence of any halide salt additive, that it is essentially insensitive to the nature of the halide in PtX2, that the best promoter in the PMexPh3-x series is PPh3 when used in strictly stoichiometric amounts, and that the 4-RC6H 5NH2 (R = nBu, Cl, OMe, NMe2) substrates are equally converted albeit less efficiently. Slight dilution of the system with THF or toluene slightly improves the activity, and a kinetic profile shows the presence of an induction phase and a deactivating step, which however does not involve reduction to metallic platinum contrary to the PPh3-free Brunet catalyst. Mechanistic considerations are presented.
Narayanan, Sankarasubbier,Prasad, Boppana P.
, p. 1204 - 1205 (1992)
A very high aniline alkylation activity under vapour-phase conditions by silica-supported vanadia catalyst is reported.
Bonnat,Hercouet,Le Corre
, p. 1579 - 1582 (1991)
A simple procedure has been described for the reduction of secondary and tertiary amides to amines using borane-dimethyl sulfide in theoretical amounts.
Yu, Xiaoli,Zhao, Ranran,Wan, Huida,Yang, Yongchun,Wang, Dawei
, p. 4588 - 4591 (2016)
An efficient synthesis of secondary amines has been described through alanine triazole iridium-catalyzed C–N bond formation of an aromatic amine and an alkyl amine using the borrowing hydrogen strategy. In addition, it was observed that alanine triazole iridium is also an efficient catalyst to promote C–N bond formation of an aromatic amine and alcohols with good to excellent yields.
Leng, Faqiang,Gerber, Iann C.,Lecante, Pierre,Bentaleb, Ahmed,Mu?oz, Antonio,Illescas, Beatriz M.,Martín, Nazario,Melinte, Georgian,Ersen, Ovidiu,Martinez, Hervé,Axet, M. Rosa,Serp, Philippe
, p. 13379 - 1338 (2017)
The C66(COOH)12 hexa-adduct has been successfully used as a building block to construct carboxylate bridged 3D networks with very homogeneous sub-1.8 nm ruthenium nanoparticles. The obtained nanostructures are active in nitrobenzene selective hydrogenation.
