88675-31-4

Basic information

• Product Name: 2-BROMO-2-PHENYL-1-(γ-FLUOROPHENYL)-ETHANONE
• Synonyms: 2-BroMo-2-phenyl-1-(4-fluorophenyl)-ethanone;Ethanone, 2-broMo-1-(4-fluorophenyl)-2-phenyl-;2-BROMO-2-PHENYL-1-(γ-FLUOROPHENYL)-ETHANONE;2-broMo-1-(4-fluorophenyl)-2-phenylethan-1-one
• CAS NO: 88675-31-4
• Molecular Formula: C₁₄H₁₀BrFO
• Molecular Weight: 293.134
• Mol File: 88675-31-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 356.4±27.0 °C(Predicted)
• Appearance: /
• Density: 1.467±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-BROMO-2-PHENYL-1-(γ-FLUOROPHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-2-PHENYL-1-(γ-FLUOROPHENYL)-ETHANONE(88675-31-4)
• EPA Substance Registry System: 2-BROMO-2-PHENYL-1-(γ-FLUOROPHENYL)-ETHANONE(88675-31-4)

Safety Data

• Hazardous Substances Data: 88675-31-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-2-PHENYL-1-(γ-FLUOROPHENYL)-ETHANONE is used as a synthetic intermediate for the development of pharmaceuticals. Its reactivity allows for the creation of a wide range of drug molecules, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 2-BROMO-2-PHENYL-1-(γ-FLUOROPHENYL)-ETHANONE serves as a key intermediate in the synthesis of various agrochemicals. Its ability to participate in multiple chemical reactions facilitates the production of effective compounds for agricultural applications.
Used in Organic Synthesis:
2-BROMO-2-PHENYL-1-(γ-FLUOROPHENYL)-ETHANONE is utilized as a versatile building block in organic synthesis. Its presence of bromine and fluorine atoms makes it a valuable component in the preparation of complex organic compounds for research and industrial purposes.

Upstream product

• 82128-66-3 2-(4-fluorophenyl)-2-(trimethylsilyloxy)acetonitrile 
• 459-57-4 4-fluorobenzaldehyde 
• 103-82-2 phenylacetic acid 
• 103-80-0 phenylacetyl chloride 
• 462-06-6 fluorobenzene 
• 347-84-2 1-(4-fluorophenyl)-2-phenylethanone 

Downstream Products

• 125971-96-2 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide 
• 347-84-2 1-(4-fluorophenyl)-2-phenylethanone 
• 936847-61-9 methyl 4-(2-(2-(4-fluorophenyl)-2-oxo-1-phenylethyl)-4-methyl-3-oxopentanamido)benzoate 
• 805241-63-8 tert-butyl 2-[(4R,6R)-6-{2-[2-(4-fluorophenyl)-4-{[4-(hydroxymethyl)phenyl]carbamoyl}-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 936756-74-0 tert-butyl 2-[(4R,6R)-6-{2-[2-(4-fluorophenyl)-4-{[4-(hydroxymethyl)phenyl]carbamoyl}-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 719-82-4 2-(4-fluorophenyl)-2-phenylacetonitrile 
• 887355-33-1 4-methyl-3-oxo-N-(2-benzyloxyphenyl)-2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]pentanamide 
• 875771-69-0 4-(4-fluorophenyl)-5-phenyl-2-thiazolehexanoic acid ethyl ester 
• 88675-42-7 1-(4-Fluoro-phenyl)-2-phenyl-2-piperidin-1-yl-ethanone 
• 88675-45-0 2-Azepan-1-yl-1-(4-fluoro-phenyl)-2-phenyl-ethanone 

Relevant articles and documents

METHOD OF PREPARING(3R,5R)-7-(2-(4-FLUOROPHENYL)-5-ISOPROPYL-3-PHENYL-4-((4-HYDROXYMETHYLPHENYLAMINO)CARBONYL)-PYRROL-1-YL)-3,5-DIHYDROXY-HEPTANOIC ACID HEMI CALCIUM SALT, AND METHOD OF PREPARING INTERMEDIATES USED THEREIN

The present invention provides a method for preparing (3R,5R)-7-(2-(4-flurophenyl)-5-isopropyl-3-phenyl-4-((4-hydroxymethylphenylamino)carbonyl)-pyrrole-1-yl)-3,5-dihydroxy heptanoic acid hemicalcium salt. The preparation method of the present invention is performed in a convergent synthesis manner in which main structural moieties of a (3R,5R)-7-(2-(4-flurophenyl)-5-isopropyl-3-phenyl-4-((4-hydroxymethylphenylamino)carbonyl)-pyrrole-1-yl)-3,5-dihydroxy heptanoic acid hemicalcium salt are independently synthesized, and then coupled. Accordingly, related substances can be easily controlled and preparing time can be reduced, thus improving the productivity of a compound, and the yield of a final compound can also be increased.

Design, synthesis and biological evaluation of novel pyrrolidone-based derivatives as potent p53-MDM2 inhibitors

Inhibition of the interactions of the tumor suppressor protein p53 with its negative regulators MDM2 in vitro and in vivo, representing a valuable therapeutic strategy for cancer treatment. The natural product chalcone exhibited moderate inhibitory activity against MDM2, thus based on the binding mode between chalcone and MDM2, a hit unsaturated pyrrolidone scaffold was obtained through virtual screening. Several unsaturated pyrrolidone derivatives were synthesized and biological evaluated. As a result, because the three critical hydrophobic pockets of MDM2 were occupied by the substituted-phenyl linked at the pyrrolidone fragment, compound 4 h demonstrated good binding affinity with the MDM2. Additionally, compound 4 h also showed excellent antitumor activity and selectivity, and no cytotoxicity against normal cells in vitro. The further antitumor mechanism studies were indicated that compound 4 h could successfully induce the activation of p53 and corresponding downstream p21 proteins, thus successfully causing HCT116 cell cycle arrest in the G1/M phase and apoptosis. Thus, the novel unsaturated pyrrolidone p53-MDM2 inhibitors could be developed as novel antitumor agents.

METHOD OF PREPARING (3R,5R)-7-(2-(4-FLUOROPHENYL)-5-ISOPROPYL-3-PHENYL-4-((4-HYDROXYMETHYLPHENYLAMINO)CARBONYL)-PYRROL-1-YL)-3,5-DIHYDROXY-HEPTANOIC ACID HEMI CALCIUM SALT, INTERMEDIATES USED THEREIN, AND METHOD OF PREPARING THE INTERMEDIATES

The present invention provides a method for manufacturing a (3r,5r)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-((4-hydroxymethylphenylamino)carbonyl)-pyrrol-1-yl)-3,5-dihydroxy-heptanoic acid hemi-calcium salt, an intermediate thereof, and a manufacturing method thereof. According to the present invention, the manufacturing method is performed in a convergent synthesis method of individually synthesizing each main structural part of the (3r,5r)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-((4-hydroxymethylphenylamino)carbonyl)-pyrrol-1-yl)-3,5-dihydroxy-heptanoic acid hemi-calcium salt and coupling the synthesized main structural parts. Accordingly, a flexible material can be easily controlled and manufacturing time can be reduced, thereby increasing productivity of a compound and yield of the final compound.COPYRIGHT KIPO 2019

Atorvastatin key intermediate for preparing environmental protection

The present invention provides a kind of atorvastatin key intermediate of environmental protection preparation method, the intermediate body is 4 - fluoro - alpha - [2 - methyl - 1 - oxygen propyl] - gama - oxo - N, beta - diphenyl benzene ding amide, the method uses hydrogen peroxide oxidation of an alkali metal salt of bromide, bromine generated in-situ, brominated 4 '- fluorophenyl - 2 - acetophenone synthesis of 2 - bromo - 1 - (4' - fluoro phenyl) - 2 - acetophenone; above brominated alkali metal salt can be the recovery of the condensation reaction by-product, the obtained 2 - bromo - 1 - (4' - fluoro phenyl) - 2 - acetophenone with isobutyryl acetyl aniline under the action of the acid condensation reaction to obtain the target product, 4 - fluoro - alpha - [2 - methyl - 1 - oxygen propyl] - gama - oxo - N, beta - diphenyl benzene ding amide. When the condensation reaction to form a brominated alkali metal salt recovery, is used for the next batch 4' - fluorophenyl - 2 - acetophenone of the bromination reaction. The method epihalogenohydrine atomic access to fully recycle, greatly reduce the emission of halogen-containing waste. The utilization rate of higher than 80%, saving, full use of resources, reduce environmental pollution, truly environmental protection.

Discovery of the First in Vivo Active Inhibitors of the Soluble Epoxide Hydrolase Phosphatase Domain

The emerging pharmacological target soluble epoxide hydrolase (sEH) is a bifunctional enzyme exhibiting two different catalytic activities that are located in two distinct domains. Although the physiological role of the C-terminal hydrolase domain is well-investigated, little is known about its phosphatase activity, located in the N-terminal phosphatase domain of sEH (sEH-P). Herein we report the discovery and optimization of the first inhibitor of human and rat sEH-P that is applicable in vivo. X-ray structure analysis of the sEH phosphatase domain complexed with an inhibitor provides insights in the molecular basis of small-molecule sEH-P inhibition and helps to rationalize the structure-activity relationships. 4-(4-(3,4-Dichlorophenyl)-5-phenyloxazol-2-yl)butanoic acid (22b, SWE101) has an excellent pharmacokinetic and pharmacodynamic profile in rats and enables the investigation of the physiological and pathophysiological role of sEH-P in vivo.

Preparation technology of atorvastatin

The invention discloses preparation technology of atorvastatin. The preparation technology comprises the following steps: a first step, the reaction of phenylacetic acid and thionyl chloride is carried out in order to obtain phenylacetyl chloride; a second step, the Friedel-Crafts acylation reaction of phenylacetyl chloride and fluorobenzene is carried out under the action of catalyst, in order to obtain 4-fluorophenyl acetophenone; a third step, 4-fluorophenyl acetophenone is brominated and the brominated 4-fluorophenyl acetophenone is reacted with N-phenyl-isobutyloylacetamide in order to obtain M-4; a fourth step, a reaction is carried out for M-4 and ATS-9 in a cyclohexane, toluene or a mixed solvent of cyclohexane and toluene, pivalic acid is used for catalysis, and a condensation product is obtained. Phenylacetyl chloride and fluorobenzene are reacted in a catalytic action of zeolite molecular sieve, a complexation reaction of the catalyst and products is avoided, reaction yield is improved, and side reactions are few in order to facilitate purification; post-treatment can be carried out for excess M-4 for recycling and reusing, reaction yield is improved, mole proportion of M-4 to ATS-9 and the addition amount of pivalic acid can be adjusted, and final yield of the reaction is improved.

BF3·OEt2-mediated [1,2]-aryl shift: Synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin

A new sequential, tandem synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin has developed. CuBr2-promoted bromination of substituted deoxybenzoins gives 2-bromo-2-arylacetophenne 3. The cyanation of 3 with sodium cyanide (NaCN) generates epoxynitrile. Then, a treatment of epoxynitrile with BF3·OEt2 results in the formation of functionalized α-arylnitriles 4 via a 1,2-aryl shift.

Copper nitrate-catalyzed α -bromination of aryl ketones with hydrobromic acid

An efficient method for α-bromination of aryl ketones, using the combination of molecular oxygen and aqueous hydrobromic acid as a brominating agent in the presence of the copper nitrate, has been developed. This catalytic system, which uses cheap and readily available reactants, shows good atom economy with water as the only by-product.

Efficient Synthesis of the Nucleus of Atorvastatin Calcium

An efficient synthetic route for the parent nucleus of atorvastatin calcium was successfully established through the modification of the related reactions. Under the optimized conditions, compound 1 was obtained in 61.2% yield (lit. 51.4%) from methyl isopropyl ketone via five steps. Two impurities generated by the aldol condensation of methyl isopropyl ketone were identified by gas chromatography-mass spectrometry and their generation can be inhibited by reducing the mixing time of methyl isopropyl ketone and NaH. One oxybromination protocol with hydrogen peroxide was employed to make the best of bromine. A debromination by-product was isolated and confirmed by 1H NMR, 13C NMR, and high-resolution mass spectrometry and its generation mechanism was discussed. The impurity can be inhibited by protecting the reaction from light and easily removed by recrystallization.

Structure-based design and synthesis of antiparasitic pyrrolopyrimidines targeting pteridine reductase 1

The treatment of Human African trypanosomiasis remains a major unmet health need in sub-Saharan Africa. Approaches involving new molecular targets are important; pteridine reductase 1 (PTR1), an enzyme that reduces dihydrobiopterin in Trypanosoma spp., has been identified as a candidate target, and it has been shown previously that substituted pyrrolo[2,3-d]pyrimidines are inhibitors of PTR1 from Trypanosoma brucei (J. Med. Chem. 2010, 53, 221-229). In this study, 61 new pyrrolo[2,3-d]pyrimidines have been prepared, designed with input from new crystal structures of 23 of these compounds complexed with PTR1, and evaluated in screens for enzyme inhibitory activity against PTR1 and in vitro antitrypanosomal activity. Eight compounds were sufficiently active in both screens to take forward to in vivo evaluation. Thus, although evidence for trypanocidal activity in a stage I disease model in mice was obtained, the compounds were too toxic to mice for further development.