N-Ethylaniline

Base Information

• Chemical Name: N-Ethylaniline
• CAS No.: 103-69-5
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 2921.42
• European Community (EC) Number: 203-135-5
• ICSC Number: 1385
• NSC Number: 8736
• UN Number: 2272
• UNII: 7E45L4I2PS
• DSSTox Substance ID: DTXSID1025271
• Nikkaji Number: J3.603J
• Wikidata: Q1959590
• ChEMBL ID: CHEMBL455541
• Mol file: 103-69-5.mol

Synonyms:N-ethylbenzenamine

Chemical Property of N-Ethylaniline

Chemical Property:

• Appearance/Colour: yellow liquid
• Vapor Pressure: 0.2 mm Hg ( 25 °C)
• Melting Point: - 63 °C
• Refractive Index: n20/D 1.554(lit.)
• Boiling Point: 201.7 °C at 760 mmHg
• PKA: 5.12(at 24℃)
• Flash Point: 85 °C
• PSA: 12.03000
• Density: 0.963 g/cm³
• LogP: 2.19140
• Storage Temp.: Store below +30°C.
• Sensitive.: Air & Light Sensitive
• Solubility.: 2.7g/l
• Water Solubility.: 50 g/L (20 ºC)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 65
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

N-Ethyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-33
• Safety Statements: 28-37-45-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CCNC1=CC=CC=C1
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Uses: N-Ethylaniline is used as an explosive stabilizer and in dyestuff manufacture. Organic synthesis. N-Ethylaniline (NEA) may be used as an internal standard in the GC analysis of nicotine extraction from nicotine gum. It may be used in the synthesis of the following, 2-(N-ethylphenylamino)-1,4-benzoquinone, 2-(arylaminomethyl)phenylboronic acid, poly(methyl methacrylate) (PMMA) films containing NEA and poly(N-ethylaniline) (PNEA).

Technology Process of N-Ethylaniline

There total 364 articles about N-Ethylaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.4%

aniline (62-53-3) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → quinoline (91-22-5) + indole (120-72-9) + 2-methylquinoline (91-63-4) + C6H4NCH2CHCCH2 (491-35-0) + N-ethyl-N-phenylamine (103-69-5)

Guidance literature:

With mesoporous nickel beta zeolite; In water; at 470 ℃; for 2h; Reagent/catalyst; Inert atmosphere; Green chemistry;

DOI:10.1039/c6ra26736j

Reference yield: 40.0%

2,3,4,5,6-Pentafluoro-benzenesulfonic acid trifluoromethyl ester + N,N-diethylaniline (91-66-7) → Pentafluorobenzene (363-72-4) + N-ethyl-N-phenylamine (103-69-5) + 2-diethylamino-2',3',4',5',6'-pentafluorobiphenyl + 4-diethylamino-2',3',4',5',6'-pentafluorobiphenyl

Guidance literature:

for 9h; Irradiation;

DOI:10.1021/jo00061a041

Reference yield:

N-methylaniline (100-61-8) + methyl iodide (74-88-4) → N-ethyl-N-phenylamine (103-69-5) + N,2-dimethylaniline (611-21-2)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1055/s-1991-26532

upstream raw materials:

methyl magnesium iodide

diethyl ether

N-phenylglycinonitrile

ethanol

Downstream raw materials:

N-ethyl-N-(2-[4]pyridyl-ethyl)-aniline

1-ethyl-4-methylquinolin-2-one

N-ethyl-3-oxo-N-phenylbutanamide

N-Aethyl-N-phenylbernsteinsaeureamid

Refernces

• 1、 Hajipour, Abdol R.,Dordahan, Fatemeh,Rafiee, Fatemeh,Mahdavi, Mohammad. "C-N cross-coupling reaction catalysed by efficient and reusable CuO/SiO2 nanoparticles under ligand-free conditions". . p. 809 - 813. Retrieved 2014.
• 2、 Makhmutov. "One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium". . p. 1166 - 1172. Retrieved 2018.
• 3、 Bethegnies, Aurelien,Dub, Pavel A.,Poli, Rinaldo. "Platinum-catalyzed assembly of quinaldine from aniline and ethylene". . p. 1882 - 1891. Retrieved 2013.
• 4、 Bonnat,Hercouet,Le Corre. "Effect of the temperature on the stoichiometry of borane dimethyl sulfide reduction of secondary and tertiary amides". . p. 1579 - 1582. Retrieved 1991.
• 5、 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. "Hexakis [60]Fullerene Adduct-Mediated Covalent Assembly of Ruthenium Nanoparticles and Their Catalytic Properties". . p. 13379 - 1338. Retrieved 2017.
• 6、 Sadykov. "Chemically induced dynamic nuclei polarization and free radicals in the reaction of triethylaluminum with nitrobenzene". . p. 1924 - 1927. Retrieved 1998.
• 7、 Gribble et al.. "-". . p. 7812. Retrieved 1974.
• 8、 Coetzee, Jacorien,Manyar, Haresh G.,Hardacre, Christopher,Cole-Hamilton, David J.. "The first continuous flow hydrogenation of amides to amines". . p. 2843 - 2847. Retrieved 2013.
• 9、 Seto,Imanari. "Synthesis of indole from aniline and ethylene glycol with Pb(II) catalysts". . p. 3139 - 3141. Retrieved 1994.
• 10、 Kishan Reddy,Periasamy. "Hydroborations, reductions and reductive iodinations using BHI2:N(C2H5)2Ph complex". . p. 8329 - 8336. Retrieved 1992.