27428-57-5

Basic information

• Product Name: 4-BROMO-4'-CHLOROBENZOPHENONE
• Synonyms: Methanone, (4-broMophenyl)(4-chlorophenyl)-;(4-bromophenyl)(4-chlorophenyl)methanone;(4-Bromophenyl)(4-chlorophenyl)methan
• CAS NO: 27428-57-5
• Molecular Formula: C₁₃H₈BrClO
• Molecular Weight: 295.57
• Mol File: 27428-57-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 148.0 to 152.0 °C
• Boiling Point: 382.7 °C at 760 mmHg
• Flash Point: 185.2 °C
• Appearance: /
• Density: 1.51 g/cm³
• Vapor Pressure: 4.64E-06mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-BROMO-4'-CHLOROBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-4'-CHLOROBENZOPHENONE(27428-57-5)
• EPA Substance Registry System: 4-BROMO-4'-CHLOROBENZOPHENONE(27428-57-5)

Safety Data

• Hazardous Substances Data: 27428-57-5(Hazardous Substances Data)

Usage

Purification Methods

Crystallise the phenone from EtOH or *C6H6 and further purify it by zone refining (100 passes) [Grove & Turner J Chem Soc 509 1929, Lin & Hanson J Phys Chem 91 2279 1987]. [Beilstein 7 II 360, 7 III 2081.]

InChI:InChI=1/C13H8BrClO/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8H

Upstream product

• 108-86-1 bromobenzene 
• 122-01-0 4-chloro-benzoyl chloride 
• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 
• 17151-48-3 tributyl(4-chlorophenyl)stannane 
• 106-37-6 1.4-dibromobenzene 
• 122334-37-6 4-chloro-N-methoxy-N-methylbenzamide 
• 104-88-1 4-chlorobenzaldehyde 
• 30203-84-0 1-bromo-4-(4-chlorobenzyl)benzene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 586-75-4 4-chlorobenzoyl chloride 
• 5575-51-9 tris(4-chlorophenyl)bismuthane 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 81223-63-4 dioxolanne de la chloro-4 bromo-4' benzophenone 
• 1063739-26-3 2-(4-bromophenyl)-4-chloromethyl-2-(4-chlorophenyl)-1,3-dioxolane 
• 1220124-27-5 [(4-bromophenyl)-(4-chlorophenyl)ketone]thiosemicarbazone 
• 1374583-54-6 (4-chlorophenyl)(4-bromophenyl)pyrimidin-5-yl methanol 
• 1395410-69-1 (4-chlorophenyl)(4'-anilinophenyl)methanone 
• 1374583-64-8 (4-chlorophenyl)(4-bromophenyl)pyrimidin-3-yl methanol 
• 78650-61-0 4-chloro-4'-isopropylbenzophenone 
• 855751-15-4 1,2-bis-(4-bromo-phenyl)-1,2-bis-(4-chloro-phenyl)-ethene 
• 81223-78-1 (methyl-4' benzenesulfonyl)-1 p-chlorobenzoyl-6 indole 
• 81223-88-3 p-chlorobenzoyl-6 indolyl-1 acetate d'ethyle 
• 81223-67-8 (azido-2 p-chlorobenzoyl-6) cinnamate de methyle 
• 81223-86-1 ethoxycarbonyl-1 p-chlorobenzoyl-6 indole 
• 81223-69-0 p-chlorobenzoyl-6 indolecarboxylate-2 de methyle 

Relevant articles and documents

Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance

Microtubule targeting agents (MTAs) are among the most successful chemotherapeutic drugs, but their efficacy is often limited by the development of multidrug resistance (MDR). Therefore, the development of novel MTAs with the ability to overcome MDR is urgently needed. In this contribution, through modification of the unsymmetric biaryl compounds, we discovered a novel compound dxy-1-175 with potent anti-proliferative activity against cancer cells. Mechanistic study revealed that dxy-1-175 inhibited tubulin polymerization by interacting with the colchicine-binding site of tubulin, which caused cell cycle arrest at G2/M phase. Based on the predicted binding model of dxy-1-175 with tubulin, a series of new 4-benzoylbiphenyl analogues were designed and synthesized. Among them, the hydrochloride compound 12e with improved solubility and good stability in human liver microsome, exhibited the most potent anti-proliferative activity with IC50 value in the low nanomolar range, and markedly inhibited the growth of breast cancer 4T1 xenograft in vivo. Notably, 12e effectively overcame P-gp-mediated MDR and our preliminary data suggested that 12e may not be a substrate of P-glycoprotein (P-gp). Taken together, our study reveals a novel MTA 12e targeting the colchicine-binding site with potent anticancer activity and the ability to circumvent MDR.

Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic controlvs.kinetic control ofN,N-Boc2-amides

A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents is reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method is highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives. Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N-C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest.

Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones

A novel and highly efficient heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl iodides with triarylbismuths has been developed that proceeds smoothly at atmospheric CO pressure and provides a general and powerful tool for the preparation of various valuable biaryl ketones with high atom economy, good to excellent yield, and recyclability of the catalyst. The reaction is the first example of Pd-catalyzed carbonylative cross-coupling for the construction of biaryl ketones using triarylbismuths as substrates.