79406-57-8

Basic information

• Product Name: 1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE
• Synonyms: 1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE;1-(3-AMINO-4-CHLOROPHENYL)ETHANONE;3'-Amino-4'-chloroacetophenone;1-(3-Amino-4-chlorophenyl)ethan-1-one, 1-(3-Amino-4-chlorophenyl)-1-oxoethane, 5-Acetyl-2-chloroaniline
• CAS NO: 79406-57-8
• Molecular Formula: C₈H₈ClNO
• Molecular Weight: 169.61
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 79406-57-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 107 °C
• Boiling Point: 322.4 °C at 760 mmHg
• Flash Point: 148.8 °C
• Appearance: /
• Density: 1.254 g/cm³
• Vapor Pressure: 0.000279mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE(79406-57-8)
• EPA Substance Registry System: 1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE(79406-57-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 79406-57-8(Hazardous Substances Data)

Usage

Description

1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE is an organic compound with the molecular formula C8H8ClNO. It is a derivative of acetophenone, featuring an amino group at the 3-position and a chlorine atom at the 4-position of the phenyl ring. 1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE serves as a key intermediate in the synthesis of various pharmaceuticals and bioactive molecules due to its unique structural features.

Uses

Used in Pharmaceutical Industry:
1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE is used as a reactant for the synthesis of 2-thiazolidinones, which are known as BRD4 inhibitors. BRD4 is a member of the bromodomain and extraterminal (BET) protein family, which plays a crucial role in cellular transcription processes. Inhibition of BRD4 has been shown to have potential therapeutic benefits in the treatment of various diseases, including cancer and inflammatory disorders.
1-(3-AMINO-4-CHLOROPHENYL)ETHAN-1-ONE's role in the synthesis of BRD4 inhibitors is significant because it can potentially lead to the development of new drugs that target these proteins, offering novel treatment options for patients suffering from diseases associated with BRD4 dysregulation.

InChI:InChI=1/C8H8ClNO/c1-5(11)6-2-3-7(9)8(10)4-6/h2-4H,10H2,1H3

Upstream product

• 5465-65-6 4-chloro-3-nitroacetophenone 
• 64-17-5 ethanol 
• 99-91-2 para-chloroacetophenone 
• 7772-99-8 stannous chloride 
• 7732-18-5 water 
• 2840-28-0 3-amino-4-chloro-benzoic acid 

Downstream Products

• 54826-14-1 1-(3-bromo-4-chlorophenyl)ethan-1-one 
• 82506-48-7 1-(4-chloro-3-iodo-phenyl)-ethanone 
• 2642-63-9 3',4'-dichloroacetophenone 
• 196408-40-9 acetic acid-(5-acetyl-2-chloro-anilide) 
• 3511-47-5 4'-chloro-3'-chlorosulfonylacetophenone 
• 61124-56-9 4'-chloro-3'-hydroxyacetophenone 
• 3843-87-6 2-chloro-5-ethyl-aniline 
• 79406-58-9 1-[4-chloro-3-[(methylsulfonyl)amino]phenyl]ethanone 
• 79406-59-0 2-bromo-1-[4-chloro-3-[(methylsulfonyl)amino]phenyl]ethanone 
• 193762-31-1 (R)-N-[5-(2-bromo-1-hydroxyethyl)-2-chlorophenyl]methanesulfonamide 
• 391904-86-2 N-[5-((1R)-2-azido-1-hydroxy-ethyl)-2-chloro-phenyl]-methanesulfonamide 
• 73898-34-7 4-chloro-3-hydroxyphenacyl bromide 
• 2350-44-9 4'-chloro-3'-sulfamoyl-acetophenone 
• 59814-17-4 2-bromo-4'-chloro-3'-sulfamoyl-acetophenone 

Relevant articles and documents

Platinum nanoparticles onto pegylated poly(lactic acid) stereocomplex for highly selective hydrogenation of aromatic nitrocompounds to anilines

A stereocomplexed poly(lactic acid)-polyethyleneglycol copolymer was synthesized and successfully used as recyclable support for Pt nanoparticles, generated by the metal vapor synthesis technique. The confinement of the Pt nanoparticles were determined by thermal analysis. Hydrogenation reactions of chlorinated aromatic nitro compounds, containing other reducible functional groups, to the corresponding anilines occurred with the latter supported Pt nanoparticles in MeOH under very mild reaction conditions (i.e. 30?°C, p(H2)?=?5.0?bar). The covalently attached polyethyleneglycol polymer significantly increased the catalytic activity of the supported Pt nanoparticles compared to an analogous catalytic system which did not contain polyethyleneglycol but the same sized Pt nanoparticles.

Fragment-based drug discovery of 2-thiazolidinones as BRD4 inhibitors: 2. Structure-based optimization

The signal transduction of acetylated histone can be processed through a recognition module, bromodomain. Several inhibitors targeting BRD4, one of the bromodomain members, are in clinical trials as anticancer drugs. Hereby, we report our efforts on discovery and optimization of a new series of 2-thiazolidinones as BRD4 inhibitors along our previous study. In this work, guided by crystal structure analysis, we reversed the sulfonamide group and identified a new binding mode. A structure-activity relationship study on this new series led to several potent BRD4 inhibitors with IC50 of about 0.05-0.1 μM in FP binding assay and GI50 of 0.1-0.3 μM in cell based assays. To complete the lead-like assessment of this series, we further checked its effects on BRD4 downstream protein c-Myc, investigated its selectivity among five different bromodomain proteins, as well as the metabolic stability test, and reinforced the utility of 2-thiazolidinone scaffold as BET bromodomain inhibitors in novel anticancer drug development.

Tricyclic compounds and drug compositions containing the same

Compounds having a β-3 adrenaline receptor agonist and are useful as drugs for the treatment and prevention of diabetes, obesity, hyperlipemia, etc., represented by a general formula (I) and salts thereof, and a process for producing these, and their intermediates, wherein R represents hydrogen or methyl; R1 represents hydrogen, halogen, hydroxy, benzyloxy, amino, or hydroxymethyl; R2 represents hydrogen, hydroxymethyl, NHR3, SO2 NR4 R4', or nitro; R6 represents hydrogen or lower alkyl; and X represents nitrogen, R9 represents hydrogen, one of R7 and R8 represent hydrogen, and the other thereof represents hydrogen, amino, acetylamino, or hydroxy.