2-(4-Chloroanilino)-1-phenyl-1-ethanone

Base Information

• Chemical Name: 2-(4-Chloroanilino)-1-phenyl-1-ethanone
• CAS No.: 53181-22-9
• Molecular Formula: C14H12ClNO
• Molecular Weight: 245.708
• Hs Code.: 2922399090
• DSSTox Substance ID: DTXSID50449748
• Nikkaji Number: J1.223.805C
• Wikidata: Q82269261
• Mol file: 53181-22-9.mol

Synonyms:53181-22-9;2-(4-Chloroanilino)-1-phenyl-1-ethanone;2-(4-Chloroanilino)-1-phenylethanone;2-((4-chlorophenyl)amino)-1-phenylethanone;2-[(4-chlorophenyl)amino]-1-phenylethan-1-one;2-(4-chlorophenylamino)-1-phenylethanone;SCHEMBL15437795;DTXSID50449748;SJWIVINUBMHTIV-UHFFFAOYSA-N;alpha-(4-Chloroanilino)acetophenone;MFCD02028817;AKOS005073439;MA-0715;2-(4-Chloroanilino)-1-phenylethan-1-one;FT-0681198;2-(4-chloro(phenylamino))-1-phenylethan-1-one;EN300-1154073;J-505235

Chemical Property of 2-(4-Chloroanilino)-1-phenyl-1-ethanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 164-166 °C
• Refractive Index: 1.634
• Boiling Point: 429.29 °C at 760 mmHg
• Flash Point: 213.427 °C
• PSA: 29.10000
• Density: 1.249g/cm³
• LogP: 3.70780
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 245.0607417
• Heavy Atom Count: 17
• Complexity: 243

Purity/Quality:

98%min ^*data from raw suppliers

2-(4-Chloroanilino)-1-phenylethan-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)CNC2=CC=C(C=C2)Cl

Technology Process of 2-(4-Chloroanilino)-1-phenyl-1-ethanone

There total 9 articles about 2-(4-Chloroanilino)-1-phenyl-1-ethanone 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: 83.0%

4-chloro-aniline (106-47-8) + α-bromoacetophenone (70-11-1) → 2-[(4-chlorophenyl)amino]-1-phenylethanone (53181-22-9)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; at 25 ℃; for 6h;

DOI:10.1016/j.tet.2004.03.036

Reference yield:

C10H13ClN2O2 + phenylmagnesium bromide (100-58-3) → 2-[(4-chlorophenyl)amino]-1-phenylethanone (53181-22-9)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 2h;

Reference yield:

phenylglyoxal hydrate (1074-12-0) + 4-chloro-aniline (106-47-8) → 2-[(4-chlorophenyl)amino]-1-phenylethanone (53181-22-9)

Guidance literature:

phenylglyoxal hydrate; 4-chloro-aniline; With [PdBr₂(BINAP)]; In tetrahydrofuran; for 0.25h; Schlenk technique; Inert atmosphere;

With hydrogen; In tetrahydrofuran; at 120 ℃; for 24h; under 41372.9 Torr; Molecular sieve; Schlenk technique;

DOI:10.1002/ejoc.201900394

upstream raw materials:

4-chloro-aniline

α-bromoacetophenone

1-phenyl-2-(p-tolylsulfonyloxy)ethanone

α-phenylsulfonyloxyacetophenone

Downstream raw materials:

1-(4-Chloro-phenyl)-4-phenyl-1H-imidazole-2-thiol

2-(4-chlorophenyl)imino-1-phenylethanone

N-Acetyl-p-chlorophenacylaniline

N,N'-bis(4-chlorophenyl)-2-oxo-2-phenylacetimidamide

Refernces

• 1、 Benitez-Medina, G. Eliad,Ortiz-Soto, Sofía,Cabrera, Armando,Amézquita-Valencia, Manuel. "Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines". . p. 3763 - 3770. Retrieved 2019/06/24.
• 2、 Peytam, Fariba,Adib, Mehdi,Shourgeshty, Reihaneh,Rahmanian-Jazi, Mahmoud,Jahani, Mehdi,Larijani, Bagher,Mahdavi, Mohammad. "A one-pot and three-component synthetic approach for the preparation of asymmetric and multi-substituted 1,4-dihydropyrazines". supporting information. . Retrieved 2019/11/11.