34841-35-5

Basic information

• Product Name: 3'-Chloropropiophenone
• Synonyms: M-CHLOROPROPIOPHENONE;MCPP;3-CHLOROPHENYL ETHYL KETONE;(3-CHLOROPHENYL)PROPAN-1-ONE;1-(3-CHLOROPHENYL)-1-PROPANONE;3-CHLORO-1-PHENYL-PROPANONE;3-CHLOROPROPIOPHENONE M-CHLORO PROPIOPHENONE;3-Chloro-Propiophenone(M-ChloroProiophenone)
• CAS NO: 34841-35-5
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.62
• EINECS: 252-242-3
• Product Categories: Aromatic Propiophenones (substituted);Aromatic Ketones (substituted);Aromatic Halides (substituted);C9;Carbonyl Compounds;Ketones
• Mol File: 34841-35-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 45-47 °C(lit.)
• Boiling Point: 124 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to light yellow/Crystalline Solid
• Density: 1.1115 (rough estimate)
• Refractive Index: 1.5350 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• CAS DataBase Reference: 3'-Chloropropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Chloropropiophenone(34841-35-5)
• EPA Substance Registry System: 3'-Chloropropiophenone(34841-35-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• WGK Germany: 3
• Hazardous Substances Data: 34841-35-5(Hazardous Substances Data)

Usage

Description

Influence of solvents and temperature on the yield and enantioselectivity of the phenylation of 3′-chloropropiophenone has been investigated.

Chemical Properties

WHITE TO LIGHT YELLOW CRYSTALLINE SOLID

Uses

Different sources of media describe the Uses of 34841-35-5 differently. You can refer to the following data:
1. 3'-Chloropropiophenone is a reagent used in the vinylation, alkylation and dienylation of ketones. It is also used in the preparation of thizaine derivatives that show antibacterial activity.
2. 3'-Chloropropiophenone has been used in the preparation of 1-(3-chlorophenyl)-1-phenyl-1-propanol.

Application

3′-Chloropropiophenone can be used as a reactant to synthesize:(S)-3-chloro-1-phenylpropanol via bio-catalyzed asymmetric reduction method.1-(3-Chlorophenyl)-1-phenyl-1-propanol by phenylation with diphenylzinc in the presence of dihydroxy bis(sulfonamide) ligand.(S)-Dapoxetine, a selective serotonin reuptake inhibitor.

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

• 766-84-7 3-chloro-benzonitrile 
• 74-96-4 ethyl bromide 
• 67-56-1 methanol 
• 120121-01-9 1-(m-Chlorophenyl)ethanol 
• 34911-51-8 2-bromo-3'-chloropropiophenone 
• 63503-60-6 3-chlorophenylboronic acid 
• 107-12-0 propiononitrile 
• 58824-53-6 1-(3-chlorophenyl)prop-2-en-1-ol 
• 79-03-8 propionyl chloride 
• 108-90-7 chlorobenzene 
• 587-04-2 m-Chlorobenzaldehyde 
• 93-55-0 1-phenyl-propan-1-one 
• 17408-16-1 3'-nitropropiophenone 
• 535-80-8 3-chlorobenzoate 

Downstream Products

• 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 
• 130839-36-0 2-(N-isopropylamino)-3'-chloropropiophenone 
• 103040-42-2 Methyl-2-(3-chlorophenyl) propanoate 
• 861965-27-7 2-[4-(3-oxo-3-phenylpropyl)piperazin-1-yl]nicotinonitrile 
• 93417-87-9 α-Ethyl-α-(3-chlorophenyl)-4-[2-(dimethylamino)-ethoxy]-benzylalcohol 
• 100306-34-1 3-chloro-1-phenylpropanol 
• 200006-14-0 N-[(3-oxo-3-phenyl)propyl]sarcosine ethyl ester 
• 200005-41-0 N-{[3-hydroxy-3-phenyl-3-(thien-2-yl)]propyl}sarcosine ethyl ester 
• 32019-30-0 (R)-1-(3-chlorophenyl)propan-1-ol 
• 172748-80-0 (S)-1-(3-chlorophenyl)propan-1-ol 

Relevant articles and documents

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.

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.

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.