N-Ethyl-4-nitroaniline

Base Information

• Chemical Name: N-Ethyl-4-nitroaniline
• CAS No.: 3665-80-3
• Molecular Formula: C8H10 N2 O2
• Molecular Weight: 166.18
• Hs Code.: 2921499090
• European Community (EC) Number: 222-927-1
• UNII: HIJ38TTD80
• DSSTox Substance ID: DTXSID3063124
• Nikkaji Number: J106.056B
• Wikidata: Q81990499
• ChEMBL ID: CHEMBL1378281
• Mol file: 3665-80-3.mol

Synonyms:N-Ethyl-4-nitroaniline;3665-80-3;N-Ethyl-p-nitroaniline;Benzenamine, N-ethyl-4-nitro-;N-ETHYL-4-NITROBENZENAMINE;HIJ38TTD80;EINECS 222-927-1;N-Ethyl-N-(4-nitrophenyl)amine;N-Ethyl-4-nitro-benzenamine;CDS1_000053;N-ethyl 4-nitroaniline;p-nitrophenyl-ethylamine;4-nitrophenyl-ethylamine;Maybridge1_002341;N1-ethyl-4-nitroaniline;UNII-HIJ38TTD80;MLS000851160;DivK1c_001093;SCHEMBL570831;ethyl-(4-nitro-phenyl)-amine;N-Ethyl-4-nitroaniline, 99%;CHEMBL1378281;DTXSID3063124;HMS548C09;ETHYL-4-NITROANILINE, N-;HMS2777B10;ANILINE, N-ETHYL-P-NITRO-;N-Ethyl-N-(4-nitrophenyl)amine #;MFCD00010647;STL069463;AKOS004896753;NCGC00246665-01;AS-76339;SMR000457403;CS-0258169;FT-0634950;EN300-69278;E85396;AE-562/43447810;J-000326

Chemical Property of N-Ethyl-4-nitroaniline

Chemical Property:

• Appearance/Colour: purple-black crystals, or yellow crystals with a blue-violet lustre
• Melting Point: 96-98 °C(lit.)
• Boiling Point: 302.3°Cat760mmHg
• PKA: 0.98±0.32(Predicted)
• Flash Point: 136.6°C
• PSA: 57.85000
• Density: 1.21g/cm³
• LogP: 2.62280
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.074227566
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

98%Min ^*data from raw suppliers

N-Ethyl-4-nitroaniline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: CCNC1=CC=C(C=C1)[N+](=O)[O-]
• Uses: N-Ethyl-4-nitroaniline is a propellant stabilizer. It is also used as building block.

Technology Process of N-Ethyl-4-nitroaniline

There total 46 articles about N-Ethyl-4-nitroaniline 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: 92.0%

ethylamine (75-04-7,85404-22-4) + 4-chlorobenzonitrile (100-00-5) → N-Ethyl-4-nitroanilin (3665-80-3)

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide; at 100 ℃; for 2.5h;

DOI:10.1007/s10562-018-2627-6

Reference yield: 85.0%

acetaldehyde (75-07-0,9002-91-9) + 4-nitro-aniline (100-01-6,104810-17-5) → N-Ethyl-4-nitroanilin (3665-80-3)

Guidance literature:

With sodium tetrahydroborate; sulfuric acid; In tetrahydrofuran; 1.) 0 deg C, 2.) room temperature, 40 min;

DOI:10.1055/s-1993-25813

Reference yield: 85.0%

p-nitrobenzene iodide (636-98-6) + N-formylethylamine (627-45-2) → N-Ethyl-4-nitroanilin (3665-80-3)

Guidance literature:

With potassium hydroxide; In neat (no solvent); at 100 ℃; for 24h; Sealed tube;

DOI:10.1021/acs.joc.8b02588

upstream raw materials:

1,3-diethyl-1,3-bis(4-nitrophenyl)urea

N-ethyl-N-(4-nitrophenyl)acetamide

ethyl-(4-nitro-phenyl)-carbamic acid ethyl ester

ethylamine

Downstream raw materials:

ethyl-(4-nitro-phenyl)-carbamoyl chloride

N-Ethyl-N,N'-diformyl-p-phenylendiamin

chloro-acetic acid-(N-ethyl-4-nitro-anilide)

N-ethyl-2,6-dibromo-4-nitro-aniline

Refernces

• 1、 Bahrami, Kiumars,Khodamorady, Minoo. "Design of BNPs-TAPC Palladium Complex as a Reusable Heterogeneous Nanocatalyst for the O-Arylation of Phenols and N-Arylation of Amines". . p. 688 - 698. Retrieved 2019/01/04.
• 2、 Deng, Danfeng,Hu, Bowen,Zhang, Ziyu,Mo, Shengkai,Yang, Min,Chen, Dafa. "Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment". . p. 2218 - 2226. Retrieved 2019/05/21.