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

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

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 
• 7772-99-8 stannous chloride 
• 7732-18-5 water 
• 2840-28-0 3-amino-4-chloro-benzoic acid 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 61124-56-9 4'-chloro-3'-hydroxyacetophenone 
• 861060-91-5 acetic acid-(5-acetyl-2-chloro-4-nitro-anilide) 
• 861060-93-7 acetic acid-(3-acetyl-6-chloro-2-nitro-anilide) 
• 13608-87-2 2',3',4'-trichloroacetophenone 
• 23082-51-1 4'-chloro-2'-nitroacetophenone 
• 6635-71-8 4,5-Dichloro-2-nitroacetophenone 
• 857560-75-9 1-(5-amino-4-chloro-2-nitro-phenyl)-ethanone 

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.

Highly chemoselective and versatile method for direct conversion of carboxylic acids to ketones utilizing zinc Ate complexes

Various carboxylic acids were directly transformed into the corresponding ketones by utilizing organozinc ate complexes, which provide high chemoselectivity without any overreaction to the undesired tertiary carbinol, owing to formation of a stable tetrahedral zincioketal intermediate. This method offers good overall atom/step/pot economy and operational simplicity. No need to overreact: Various carboxylic acids were directly transformed to the corresponding ketones by utilizing organozinc ate complexes, which provide high chemoselectivity without any overreaction to undesired tertiary carbinol, owing to formation of a stable tetrahedral zincioketal intermediate. This method offers good overall atom/step/pot economy and operational simplicity.

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.

N-Glycine-sulfonamides as potent dual orexin 1/orexin 2 receptor antagonists

A series of dual OX1R/OX2R orexin antagonists was prepared based on a N-glycine-sulfonamide core. SAR studies of a screening hit led to compounds with low nanomolar affinity for both receptors and good oral bioavailability. One of these compounds, 47, has demonstrated in vivo activity in rats following oral administration.

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.

Process for preparing aromatic amines

The present invention relates to a process for preparing aromatic amines by reacting an aromatic nitro compound with carbon monoxide in a solvent mixture comprising water and a water-insoluble organic solvent by means of a catalyst comprising palladium and a water-soluble phosphine under a pressure of from 5 to 300 bar and at a temperature of from 50 to 200° C., and separating the aqueous phase and the organic phase.

Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N'-(3-substituted phenyl)-N'-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers

In the mammalian central nervous system, the N-methyl-D-aspartate (NMDA) subclass of glutamate receptors may play an important role in brain diseases such as stroke, brain or spinal cord trauma, epilepsy, and certain neurodegenerative diseases. Compounds which specifically antagonize the actions of the neurotransmitter glutamate at the NMDA receptor ion-channel site offer a novel approach to treating these disorders. CERESTAT (4, aptiganel CNS 1102) is currently undergoing clinical trial for the treatment of traumatic brain injury and stroke. Previously, we reported that analogues of N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine (4) bound to the NMDA receptor ion-channel site with high potency and selectivity. Recently, molecules active at both σ receptors and NMDA receptor sites were investigated. A series of substituted diphenylguanidines 6 which are structurally related to N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine was prepared. Compounds containing appropriate substitution/pattern in one of the phenyl rings of diphenylguanidines displayed high affinity. For example, N-(2,5-dibromophenyl)-N'-(3-ethylphenyl)-N'-methylguanidine (27b, R2 = R5 = Br, R3 = C2H5) exhibited potency at both 5 receptors and NMDA receptor sites; 27b also showed high efficacy in vivo in a neonatal rat excitotoxicity model. Further studies indicated that substituent effects were important in this compound series, and 2,5-disubstituted phenyl was the preferred substitution pattern for high-affinity binding at NMDA receptor sites. Bromo and methylthio were the optimal substituents for the R2 and R5 positions of the 2,5-disubstituted phenyl group, respectively. N-(2-Bromo-5- (methylthio)phenyl)-N'-(3-ethylphenyl)-N'-methylguanidine (34b, R2 = Br, R5 = SMe, R3 = C2H5) was highly active at NMDA receptor sites. We found that the binding affinity of guanidines of type 6 could be further enhanced with the appropriate substitution at R3. Optimal activity in this series are afforded by 43b and 44b (R2 = Cl or Br, R5 = R3 = SCH3). Both 43b and 44b bound to NMDA receptor sites with high potency and selectivity (K(i) vs [3H]MK-801: 1.87 and 1.65 nM, respectively); these compounds are active in vivo in various animal models of neuroprotection. The structure-activity relationships for these compounds at the NMDA receptor ion-channel site are discussed.

First Selective Reduction of Aromatic Nitro Compounds Using Water Soluble Catalysts

A new methodology has been developed which involves the reduction of substituted nitro aromatics to substituted anilines using a two phase system with water - soluble palladium catalysts.The nitro group was reduced selectively to an amine in up to 85percent yield whereby other functional groups i.e., ketone, nitrile, chloride and alkene were untouched.

1-MERCAPTOACYL-3-[(AMINOSULFONYL)PHENYL]-4,5-DIHYDRO-1H-PYRAZOLE-5-CARBOXYLIC ACID

Compounds having the formula STR1 wherein R 1 is hydrogen, alkyl, aryl, arylalkyl or a hydrolyzable acyl protecting group; R 2 is hydrogen, alkyl or trifluoromethyl; R 3 and R 4 each is independently hydrogen, halogen, trifluoromethyl, alkylamino, furylmethylamino, phenylamino, thienylmethylamino, alkoxy, aryloxy, benzylthio, arylthio, benzyl, benzoyl, hydroxy, cyano or arylmethoxy; R 5 is hydrogen, alkyl or arylalkyl; andn is 0, 1 or 2, have hypotensive activity.