388091-63-2

Basic information

• Product Name: 3'-CHLORO-3-PHENYLPROPIOPHENONE
• Synonyms: 3'-CHLORO-3-PHENYLPROPIOPHENONE
• CAS NO: 388091-63-2
• Molecular Formula: C₁₅H₁₃ClO
• Molecular Weight: 244.72
• Mol File: 388091-63-2.mol

Chemical Properties

• Boiling Point: 386°C at 760 mmHg
• Flash Point: 214.7°C
• Appearance: /
• Density: 1.164g/cm³
• Vapor Pressure: 3.66E-06mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: 3'-CHLORO-3-PHENYLPROPIOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-CHLORO-3-PHENYLPROPIOPHENONE(388091-63-2)
• EPA Substance Registry System: 3'-CHLORO-3-PHENYLPROPIOPHENONE(388091-63-2)

Safety Data

• Hazardous Substances Data: 388091-63-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H13ClO/c16-14-8-4-7-13(11-14)15(17)10-9-12-5-2-1-3-6-12/h1-8,11H,9-10H2

Upstream product

• 63503-60-6 3-chlorophenylboronic acid 
• 645-45-4 hydrocinnamic acid chloride 
• 20426-48-6 6-chloro-2-phenyl-4H-chromen-4-one 
• 99-02-5 3'-Chloroacetophenone 
• 100-51-6 benzyl alcohol 
• 120121-01-9 1-(m-Chlorophenyl)ethanol 
• 100-52-7 benzaldehyde 
• 20426-48-6 (E)-1-(3-chlorophenyl)-3-phenylprop-2-en-1-one 
• 16616-38-9 1-(3-chlorophenyl)-3-phenyl-2-propyn-1-one 
• 100-42-5 styrene 
• 535-80-8 3-chlorobenzoate 

Downstream Products

• 1176789-20-0 C₁₆H₁₆ClN₃S 

Relevant articles and documents

Nickel-catalyzed α-alkylation of ketones with benzyl alcohols

We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.

Electrochemical-Induced Hydrogenation of Electron-Deficient Internal Olefins and Alkynes with CH3OH as Hydrogen Donor

Efficient hydrogenation of electron-deficient internal olefins and alkynes access to saturate ketone with CH3OH as a single hydrogen donor under electrochemical conditions has been successfully developed. This hydrogenation strategy can be used to convert electron-deficient internal olefins and alkynes to saturate ketone under electrochemical conditions with exogenous-reductant and a metal catalyst. Mechanistic studies reveal that radical hydrogenation was involved in this transformation. Notably, various electron-deficient internal olefins and alkynes could be tolerated in such an electrochemical hydrogenation synthetic strategy and can be easily scaled up with good efficiency. (Figure presented.).

Preparation method of novel aromatic ketone compound

The invention discloses a preparation method of a novel aromatic ketone compound. According to the preparation method, an aromatic carboxylic acid compound and an aromatic olefin compound are used asreaction raw materials, triphenylphosphine is taken as a deoxidizing reagent, Methylenene blue is taken as a photocatalyst, stirring and reacting are carried out at room temperature in an N,N-dimethylacetamide solvent under the irradiation of a white light lamp in a nitrogen atmosphere and under the condition of taking 2,4,6-trimethylpyridine as an alkali, thereby obtaining a target product, namely the aromatic ketone compound. The method has the advantages of mild reaction conditions, simplicity in operation, low cost, convenience in purification, environmental friendliness and the like.

Method for synthesizing alpha-alkyl ketone

The invention discloses a method for synthesizing alpha-alkyl ketone, and especially includes the following steps of: in a reaction vessel, adding secondary alcohol, a transition metal catalyst, and a solvent tertiary amyl alcohol; and heating and refluxing a reaction mixture in an oil bath for several hours, cooling the mixture to a room temperature; then adding primary alcohol and alkali, heating and refluxing the reaction mixture for several hours, and then obtaining a target compound through column separation. The method for synthesizing the alpha-alkyl ketone starts from the primary alcohol and the secondary alcohol. With the participation of the transition metal catalyst, the alpha-alkyl ketone is generated through a serial secondary alcohol non-acceptor dehydrogenation oxidation reaction/alpha-alkylation reaction of ketone. The reaction shows three obvious advantages that 1) non-toxic alcohols are used as the starting materials; 2) only hydrogen and water are generated in the reaction without environmental hazards; 3) atomic economy is high in the reaction; and 4) only 0.1 equivalents of carbonate is needed for the reaction, and the reaction only takes 3-6 hours. Therefore, the reaction meets the requirements of green chemistry and has broad development prospects.

Synthesis and catalytic applications of ruthenium(ii)-phosphino-oxime complexes

In this work, the preparation of the first ruthenium complexes containing a phosphino-oxime ligand is presented. Thus, the reaction of cis-[RuCl2(DMSO)4] (3) with 2.4 equivalents of 2-Ph2PC6H4CH=NOH (1) in refluxing THF led to the clean formation of the octahedral ruthenium(ii) derivative cis,cis,trans-[RuCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}2] (5), whose structure was unambiguously confirmed by means of a single-crystal X-ray diffraction study. Complex 5 could also be synthesized from the reaction of the dimer [{RuCl(μ-Cl)(η6-p-cymene)}2] (4) with an excess of 1 in refluxing toluene. Treatment of 4 with 2 equivalents of 1, in CH2Cl2 at r.t., allowed also the preparation of the half-sandwich Ru(ii) derivative [RuCl{κ2-(P,N)-2-Ph2PC6H4CH=NOH}(η6-p-cymene)][PF6] (6). In addition, complexes 5 and 6 proved to be active catalysts for the rearrangement of aldoximes to primary amides, as well as for the α-alkylation/reduction of acetophenones with primary alcohols, with the former showing the best performances in both processes.

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

Synthesis of a-Alkylated Ketones via Tandem Acceptorless Dehydrogenation/a-Alkylation from Secondary and Primary Alcohols Catalyzed by Metal-Ligand Bifunctional Iridium Complex [CpIr(2,2′-bpyO)(H2O)]

A new strategy for the synthesis of α-alkylated ketones via tandem acceptorless dehydrogenation/α-alkylation from secondary and primary alcohols was proposed and accomplished. In the presence of metal-ligand bifunctional iridium complex [CpIr(2,2′-bpyO)(H2O)], various desirable products were obtained in high yields. Compared with previous methods for the direct dehydrogenative coupling of secondary alcohols with primary alcohols to α-alkylated ketones, this protocol has obvious advantages including complete selectivity for α-alkylated ketones and more environmentally benign conditions. Notably, the study also exhibited the potential to develop tandem reactions catalyzed using a metal-ligand bifunctional iridium complex.

A base-controlled chemoselective transfer hydrogenation of α,β-unsaturated ketones catalyzed by [IrCpCl2]2 with 2-propanol

A simple homogeneous catalyst system based on commercially available [IrCpCl2]2 has been developed for the conjugate reduction of α,β-unsaturated ketones. Under the optimized conditions, a wide range of α,β-unsaturated ketones were reduced to saturated ketones in 83-98% yield. While switching the base from K2CO3 to KOH, saturated alcohols was selectively obtained.

Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatB

Human African trypanosomiasis (HAT) is caused by the protozoan parasite Trypanosoma brucei. The cysteine proteases of T. brucei have been shown to be crucial for parasite replication and represent an attractive point for therapeutic intervention. Herein we describe the synthesis of a series of thiosemicarbazones and their activity against the trypanosomal cathepsins TbcatB and rhodesain, as well as human cathepsins L and B. The activity of these compounds was determined against cultured T. brucei, and specificity was assessed with a panel of four mammalian cell lines.