34841-35-5

Usage

Uses

Used in Chemical Synthesis:
3'-Chloropropiophenone is used as a reagent for the vinylation, alkylation, and dienylation of ketones, which are essential processes in the creation of various chemical compounds.
Used in Pharmaceutical Industry:
3'-Chloropropiophenone is used as a reactant to synthesize (S)-3-chloro-1-phenylpropanol through a bio-catalyzed asymmetric reduction method. 3'-Chloropropiophenone has potential applications in the development of pharmaceuticals.
Used in Organic Chemistry:
It is also used in the preparation of 1-(3-chlorophenyl)-1-phenyl-1-propanol, a compound that may have various applications in organic chemistry.
Used in Antibacterial Agents:
3'-Chloropropiophenone is utilized in the preparation of thizaine derivatives, which exhibit antibacterial activity. This makes it a valuable component in the development of new antimicrobial agents.
Used in Selective Serotonin Reuptake Inhibitors (SSRIs):
3'-Chloropropiophenone is employed in the synthesis of (S)-Dapoxetine, a selective serotonin reuptake inhibitor, which is an important class of drugs used to treat depression and anxiety disorders.

Preparation

4.86 g (0.2 mol) of magnesium turnings, 30 ml of dry diethyl ether and a grain of iodine are placed in a one liter three-necked round-bottomed flask equipped with a condenser, a calcium chloride drying tube, a pressure equalizing funnel and a magnetic stirrer; the flask is purged with nitrogen, and 21.8 g (0.2 mol) of ethyl bromide in 30 ml of dry diethyl ether are then added. The mixture is then heated under reflux for one hour and left to cool. At ambient temperature, 16.51 g (0.12 mol) of 3-chlorobenzonitrile in 70 ml of dry diethyl ether are then added. A copious precipitate forms. The mixture is stirred overnight at ambient temperture and then cooled in an ice bath and hydrolysed by slowly adding 50 ml of water and then about 100 ml of 6N hydrochloric acid until the pH is acid. The mixture is stirred for one and a half hours and then extracted with ethyl acetate. The organic extract is then washed twice with water, dried and concentrated on a rotary evaporator. This gives 26 g of an orange oil, which is concentrated in vacuo to give about 18.2 g of ochre crystals of 3'-chloropropiophenone melting at about 40° C.Literature source US04690931

Upstream product

• 28145-63-3 m-Chlorthiobenzoesaeure-S-ethylester 
• 999-75-7 ethylzinc iodide 
• 766-84-7 3-chloro-benzonitrile 
• 93-55-0 1-phenyl-propan-1-one 
• 535-80-8 3-chlorobenzoate 
• 74-96-4 ethyl bromide 
• 79-03-8 propionyl chloride 
• 108-90-7 chlorobenzene 
• 63503-60-6 3-chlorophenylboronic acid 
• 107-12-0 propiononitrile 
• 34911-51-8 2-bromo-3'-chloropropiophenone 
• 67-56-1 methanol 
• 120121-01-9 1-(m-Chlorophenyl)ethanol 
• 58824-53-6 1-(3-chlorophenyl)prop-2-en-1-ol 

Downstream Products

• 57430-24-7 3-propylchlorobenzene 
• 103-65-1 phenylpropane 
• 93-54-9 1-Phenyl-1-propanol 
• 93-55-0 1-phenyl-propan-1-one 
• 1049974-44-8 1-(3-Chloro-phenyl)-2-(1,1-dimethyl-propylamino)-propan-1-one 
• 119802-69-6 2-Amino-1-(3-chloro-phenyl)-propan-1-one 
• 34841-39-9 bupropion 
• 32019-30-0 (+/-)-1-(3'-chlorophenyl)propan-1-ol 
• 1019505-14-6 [1-(3-chloro-phenyl)-propylamino]-acetic acid methyl ester 
• 40023-86-7 1-(3-chlorophenyl)propylamine 

Relevant academic research and scientific papers

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

Novel benzene-based carbamates for ache/bche inhibition: Synthesis and ligand/structure-oriented sar study

A series of new benzene-based derivatives was designed, synthesized and comprehensively characterized. All of the tested compounds were evaluated for their in vitro ability to potentially inhibit the acetyl-and butyrylcholinesterase enzymes. The selectivity index of individual molecules to cholinesterases was also determined. Generally, the inhibitory potency was stronger against butyryl-compared to acetylcholinesterase; however, some of the compounds showed a promising inhibition of both enzymes. In fact, two compounds (23, benzyl ethyl(1-oxo-1-phenylpropan-2-yl)carbamate and 28, benzyl (1-(3-chlorophenyl)-1-oxopropan-2-yl) (methyl)carbamate) had a very high selectivity index, while the second one (28) reached the lowest inhibitory concentration IC50 value, which corresponds quite well with galanthamine. Moreover, comparative receptor-independent and receptor-dependent structure–activity studies were conducted to explain the observed variations in inhibiting the potential of the investigated carbamate series. The principal objective of the ligand-based study was to comparatively analyze the molecular surface to gain insight into the electronic and/or steric factors that govern the ability to inhibit enzyme activities. The spatial distribution of potentially important steric and electrostatic factors was determined using the probability-guided pharmacophore mapping procedure, which is based on the iterative variable elimination method. Additionally, planar and spatial maps of the host–target interactions were created for all of the active compounds and compared with the drug molecules using the docking methodology.

Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.

Nickel-Catalyzed Addition of Arylboronic Acids to Alkyl Nitriles for Synthesis of Aryl Ketones in Fluorinated Solvent

A mild and efficient nickel-catalyzed addition of arylboronic acids to alkyl nitriles in a fluorinated solvent for the synthesis of various aryl ketones is described. A broad range of arylboronic acids and alkyl nitriles were investigated, and the desired products were obtained with good to excellent yields under the optimized conditions. This method provides an opportunity for the synthesis of aryl ketones from alkyl nitriles, especially acetonitrile, with a non-noble metal catalyst in one pot.

Reactions catalyzed by a binuclear copper complex: Selective oxidation of alkenes to carbonyls with O2

Terminal alkenes were selectively cleaved into ketones and aldehydes catalyzed by a binuclear copper catalyst bearing a simple salicylate ligand with O2 as the oxidant. The reaction was carried out under an atmosphere of O2 (balloon) with 0.5 mol% of catalyst and could be performed on a gram scale, providing a convenient and practical method for the cleavage of terminal alkenes into carbonyl compounds.

Method for synthesizing m-chlorophenylacetone

The invention discloses a method for synthesizing m-chlorophenylacetone. The method comprises the following steps: generating a Grignard reagent from magnesium and bromoethane in a tetrahydrofuran (THF) solution, and performing a reaction on the Grignard reagent and m-chlorobenzonitrile, thereby obtaining m-chlorophenylacetone. The method is simple to operate, advanced in process and easy in industrial production, and a solvent can be recycled. The yield of the m-chlorophenylacetone generated by using the method is up to 92.6%, and the liquid-phase purity of the m-chlorophenylacetone can be up to 99.93% or greater.

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.

A chemoselective α-aminoxylation of aryl ketones: a cross dehydrogenative coupling reaction catalysed by Bu4NI

Tetrabutyl ammonium iodide (TBAI) catalyzed α-aminoxylation of ketones using aq. TBHP as an oxidant has been accomplished. We have shown that the CDC (cross dehydrogenative coupling) reactions of ketones with N-hydroxyimidates such as N-hydroxysuccinimide (NHSI), N-hydroxyphthalimide (NHPI), N-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) lead to the corresponding oxygenated products in good to moderate yields. The application of this method has been demonstrated by transforming a few coupled products into synthetically useful intermediates and products.

N, N′-dioxide-Cu(OTf)2 complex catalyzed highly enantioselective amination reaction of N-acetyl enamide

The N,N′-dioxide-Cu(OTf)2 complexes were applied in the asymmetric amination reaction of N-acetyl enamides with dialkyl azodicarboxylate, giving the corresponding products in good yields with high enantioselectivities (up to 91% ee). Precursors of vicinal diamine were readily obtained with excellent diastereoselectivities (>95:5) by NaBH4 reduction.

First catalytic and green synthesis of aryl-(Z)-vinyl chlorides and its plausible addition-elimination mechanism

(Chemical Equation Presented) Via a catalytic cycle in the presence of scandium triflate (2 mol %)/DMF (1 mol %)/benzoyl chloride (5 mol %), aromatic ketones were treated with bis(trichloromethyl) carbonate (BTC) to afford aryl-(Z)-vinyl chlorides. All metal triflates tested in the reaction showed highly catalytic activity. A plausible addition-elimination mechanism was proposed. The present work describes the first catalytic and green route to the synthesis of aryl-(Z)-vinyl chlorides.