1-(3-Amino-4-chlorophenyl)ethanone

Base Information

• Chemical Name: 1-(3-Amino-4-chlorophenyl)ethanone
• CAS No.: 79406-57-8
• Molecular Formula: C8H8ClNO
• Molecular Weight: 169.611
• Hs Code.: 2922390090
• European Community (EC) Number: 835-520-4
• DSSTox Substance ID: DTXSID70380866
• Wikidata: Q82171350
• Mol file: 79406-57-8.mol

Synonyms:79406-57-8;1-(3-Amino-4-chlorophenyl)ethan-1-one;1-(3-amino-4-chlorophenyl)ethanone;3-Amino-4-chloroacetophenone;3'-Amino-4'-chloroacetophenone;Ethanone, 1-(3-amino-4-chlorophenyl)-;MFCD00122619;3-amino-4-chloro-acetophenone;SCHEMBL7105778;DTXSID70380866;CELXPDXOZXEXJX-UHFFFAOYSA-N;AMY14469;STL370545;AKOS016000262;PS-4376;1-(3-amino-4-chlorophenyl)ethane-1-one;1-(3-azanyl-4-chloranyl-phenyl)ethanone;AC-28638;CS-0043787;FT-0690643;EN300-62333;1-(3-Amino-4-chlorophenyl)ethanone, AldrichCPR;A839675;Z979493752

Chemical Property of 1-(3-Amino-4-chlorophenyl)ethanone

Chemical Property:

• Vapor Pressure: 0.000279mmHg at 25°C
• Melting Point: 107 °C
• Refractive Index: 1.586
• Boiling Point: 322.4 °C at 760 mmHg
• Flash Point: 148.8 °C
• Density: 1.254 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 169.0294416
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

98% ^*data from raw suppliers

1-(3-Amino-4-chlorophenyl)ethan-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC(=C(C=C1)Cl)N
• Uses: 1-(3-amino-4-chlorophenyl)ethan-1-one is a useful reactant for the synthesis of 2-thiazolidinones as BRD4 inhibitors.

Technology Process of 1-(3-Amino-4-chlorophenyl)ethanone

There total 9 articles about 1-(3-Amino-4-chlorophenyl)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: 100.0%

4-chloro-3-nitroacetophenone (5465-65-6) → 3-amino-4-chloroacetophenone (79406-57-8)

Guidance literature:

With hydrogenchloride; stannous chloride dihydrate; In methanol; water; Reflux;

DOI:10.1016/j.bmcl.2008.09.079

Reference yield: 88.0%

3-amino-4-chloro-benzoic acid (2840-28-0) + 4CH3(1-)*Zn(2+)*Li(1+) → 3-amino-4-chloroacetophenone (79406-57-8)

Guidance literature:

3-amino-4-chloro-benzoic acid; 4CH₃^(1-)*Zn⁽²⁺⁾*Li⁽¹⁺⁾; In tetrahydrofuran; diethyl ether; hexane; at 20 ℃; Schlenk technique; Inert atmosphere;

With iodine; In tetrahydrofuran; diethyl ether; hexane; at 20 ℃; Solvent; chemoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/asia.201500308

Reference yield: 70.0%

4-chloro-3-nitroacetophenone (5465-65-6) → 3-amino-4-chloroacetophenone (79406-57-8) + 1-[3-(5-Acetyl-2-chloro-phenyl-NNO-azoxy)-4-chloro-phenyl]-ethanone

Guidance literature:

With carbon monoxide; hexasulfonated 2,2'-bis-diphenylphosphinomethylene binaphthyl; palladium dichloride; In water; xylene; at 100 ℃; for 20h; under 90007.2 Torr; Yields of byproduct given;

DOI:10.1016/0040-4039(95)02003-8

upstream raw materials:

4-chloro-3-nitroacetophenone

ethanol

para-chloroacetophenone

stannous chloride

Downstream raw materials:

4'-chloro-3'-hydroxyacetophenone

4'-chloro-3'-chlorosulfonylacetophenone

acetic acid-(5-acetyl-2-chloro-anilide)

3',4'-dichloroacetophenone

Refernces

• 1、 Zhao, Lele,Wang, Yingqing,Cao, Danyan,Chen, Tiantian,Wang, Qi,Li, Yanlian,Xu, Yechun,Zhang, Naixia,Wang, Xin,Chen, Danqi,Chen, Lin,Chen, Yue-Lei,Xia, Guangxin,Shi, Zhe,Liu, Yu-Chih,Lin, Yijyun,Miao, Zehong,Shen, Jingkang,Xiong, Bing. "Fragment-based drug discovery of 2-thiazolidinones as BRD4 inhibitors: 2. Structure-based optimization". . p. 1281 - 1297. Retrieved 2015/03/04.
• 2、 Aissaoui, Hamed,Koberstein, Ralf,Zumbrunn, Cornelia,Gatfield, John,Brisbare-Roch, Catherine,Jenck, Francois,Treiber, Alexander,Boss, Christoph. "N-Glycine-sulfonamides as potent dual orexin 1/orexin 2 receptor antagonists". scheme or table. p. 5729 - 5733. Retrieved 2009/06/30.