3946-29-0

Usage

Uses

Used in Pharmaceutical Industry:
3,4'-Dichloropropiophenone is used as a reagent for the preparation of antidepressant aryl-alkyl-piperidine derivatives. Its chemical properties allow it to play a crucial role in the synthesis of these compounds, which are essential for the development of new treatments for depression.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3,4'-Dichloropropiophenone is utilized in the creation of mGlu5 receptor negative allosteric modulators. These modulators are significant in the study and treatment of various neurological disorders, as they can help regulate the activity of specific receptors in the brain.
Used in Cancer Research:
3,4'-Dichloropropiophenone is also employed in the genetic screening of compounds that counter the growth of methylthioadenosine phosphorylase, an enzyme involved in the spread of cancer. Its use in this context aids researchers in identifying potential therapeutic agents that can help combat cancer progression.

Synthetic route

chlorobenzene (108-90-7) + 2-chloropropionyl chloride (625-36-5) → 3,4'-Dichloropropiophenone (3946-29-0)

Conditions	Yield
With aluminium trichloride In carbon disulfide for 3h;	89%
With aluminum (III) chloride Friedel Crafts acylation;	87%
With carbon disulfide; aluminium trichloride

ethene (74-85-1) + 4-chloro-benzoyl chloride (122-01-0) → 3,4'-Dichloropropiophenone (3946-29-0)

Conditions	Yield
With zinc(II) chloride In dichloromethane at 0 - 10℃; for 2h;

3,4'-Dichloropropiophenone (3946-29-0) → 3-chloro-1-(4-chlorophenyl)propan-1-ol (25574-18-9)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 2h;	99%
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 2h;	35%
With lithium aluminium tetrahydride In diethyl ether

morpholine (110-91-8) + 3,4'-Dichloropropiophenone (3946-29-0) → 1-(4-chlorophenyl)-3-(morpholin-1-yl)propane-1-one hydrochloride (30412-07-8)

Conditions	Yield
In tetrahydrofuran at 20℃; for 16h;	99%
	99%

1-methyl-piperazine (109-01-3) + 3,4'-Dichloropropiophenone (3946-29-0) → 1-(4-chlorophenyl)-3-(4-methylpiperazin-1-yl)propane-1-one hydrochloride

Conditions	Yield
In tetrahydrofuran at 20℃; for 16h;	98%

1-methyl-piperazine (109-01-3) + 3,4'-Dichloropropiophenone (3946-29-0) → 1-(4-chloro-phenyl)-3-(4-methyl-piperazin-1-yl)-propan-1-one (60868-02-2)

Conditions	Yield
	98%

methyl magnesium iodide (917-64-6) + 3,4'-Dichloropropiophenone (3946-29-0) → 3-(4-Chlorophenyl)-3-hydroxy-3-methyl-1-chloropropane (113696-77-8)

Conditions	Yield
In benzene for 1h;	95%

N-methyl-N-allylamine (627-37-2) + 3,4'-Dichloropropiophenone (3946-29-0) → 3-(allylmethylamino)-1-(4-chlorophenyl)propan-1-one (1236376-76-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 18h;	94%

3,4'-Dichloropropiophenone (3946-29-0) → (-)-3-chloro-1-(4-chlorophenyl)propan-1-ol

Conditions	Yield
Stage #1: 3,4'-Dichloropropiophenone With (S)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; phenylsilane; copper(II) acetate monohydrate In toluene at -20 - 20℃; for 48h; Stage #2: With hydrogenchloride In water; toluene Reagent/catalyst; enantioselective reaction;	93%

3,4'-Dichloropropiophenone (3946-29-0) + triethyl phosphite (122-52-1) → [3-(4-Chloro-phenyl)-3-oxo-propyl]-phosphonic acid diethyl ester (16324-11-1)

Conditions	Yield
for 2h; Heating;	92%
at 85℃; Rate constant; Thermodynamic data; Kinetics; Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.); other substituted 3-chloropropiophenones; other solvents;
at 85 - 100℃; Rate constant; Thermodynamic data; Ea, ΔH, ΔS, ΔG;

3,4'-Dichloropropiophenone (3946-29-0) + 4-methylphenylboronic acid (5720-05-8) → 1-(4-chlorophenyl-)-3-(4-tolyl-)-propane-2-one-1

Conditions	Yield
With potassium phosphate; Wilkinson's catalyst; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 20h; Inert atmosphere;	92%

3,4'-Dichloropropiophenone (3946-29-0) → p-chlorophenyl vinyl ketone (7448-87-5)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 4h; Cooling with ice;	91%
With triethylamine In chloroform at 20℃; for 18h; Inert atmosphere;	86%
With isobutylamine In acetonitrile at 25℃; Rate constant; kinetic isotope effect;

3,4'-Dichloropropiophenone (3946-29-0) + phenylboronic acid (98-80-6) → 4'-chloro-3-phenylpropiophenone (5739-37-7)

Conditions	Yield
With potassium phosphate; Wilkinson's catalyst; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 20h; Inert atmosphere;	90%

3,4'-Dichloropropiophenone (3946-29-0) + bis(pinacol)diborane (73183-34-3) → C15H20BClO3

Conditions	Yield
Stage #1: bis(pinacol)diborane With potassium phosphate; copper(l) iodide In tert-Amyl alcohol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4'-Dichloropropiophenone In tert-Amyl alcohol at 60℃; for 20h; Inert atmosphere;	87%

3,4'-Dichloropropiophenone (3946-29-0) + 4-Chlorophenylboronic acid (1679-18-1) → 1,3-Bis(4-chlorophenyl)-1-propanone (97009-36-4)

Conditions	Yield
With potassium phosphate; Wilkinson's catalyst; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 20h; Inert atmosphere;	86%

iodobenzene (591-50-4) + 3,4'-Dichloropropiophenone (3946-29-0) → (E)-1-(4-chlorophenyl)-3-phenyl-2-propen-1-one (22966-22-9)

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 20 - 90℃; under 750.075 Torr; for 16h; Inert atmosphere;	86%

3,4'-Dichloropropiophenone (3946-29-0) + ethyl 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylate (51940-43-3) → 2-{4-[3-(4-Chloro-phenyl)-3-oxo-propyl]-piperazin-1-yl}-8-ethyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (68689-97-4)

Conditions	Yield
With triethylamine In isopropyl alcohol Heating;	85%

Togni's reagent II (887144-94-7) + 3,4'-Dichloropropiophenone (3946-29-0) → 2-chloro-1-(4-chlorophenyl)-4,4,4-trifluorobutan-1-one

Conditions	Yield
With 9,10-dihydro-10-methylacridine In 1,2-dichloro-ethane; acetonitrile at 60℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;	84%

(R,S)-5,5-dimethyl-4-ethoxycarbonylthiazolidine (133937-67-4) + 3,4'-Dichloropropiophenone (3946-29-0) → 1-(4-chlorophenyl)-3-(5,5-dimethyl-4-ethoxycarbonyl-3-thiazolidinyl)propan-1-one (133914-13-3)

Conditions	Yield
	83.6%

1H-imidazole (288-32-4) + 3,4'-Dichloropropiophenone (3946-29-0) → 1-(4-chlorophenyl)-3-(1H-imidazole-1-yl)propan-1-one (113193-72-9)

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; for 72h;	81%

3,4'-Dichloropropiophenone (3946-29-0) → 1-(4-chlorophenyl)-3-nitro-1-propanone (62847-53-4)

Conditions	Yield
	80%
With 3,5-dihydroxyphenol; sodium nitrite

piperidine (110-89-4) + 3,4'-Dichloropropiophenone (3946-29-0) → 1-(4-chlorophenyl)-3-(piperidin-1-yl)propane-1-one hydrochloride (5250-05-5)

Conditions	Yield
In tetrahydrofuran at 20℃; for 16h;	80%
Stage #1: piperidine; 3,4'-Dichloropropiophenone In tetrahydrofuran for 12h; Stage #2: With hydrogenchloride In diethyl ether	80%

3,4'-Dichloropropiophenone (3946-29-0) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 1-(4-chlorophenyl)-3-(4-(trifluoromethyl)phenyl)propan-1-one

Conditions	Yield
With potassium phosphate; Wilkinson's catalyst; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 20h; Inert atmosphere;	80%

3,4'-Dichloropropiophenone (3946-29-0) + vinyl magnesium bromide (1826-67-1) → 5-chloro-3-(4-chlorophenyl)pent-1-en-3-ol

Conditions	Yield
Stage #1: vinyl magnesium bromide With cerium(III) chloride heptahydrate In tetrahydrofuran at -78℃; for 0.75h; Inert atmosphere; Stage #2: 3,4'-Dichloropropiophenone In tetrahydrofuran at -78℃; for 3h; Inert atmosphere;	78%
With cerium(III) chloride In tetrahydrofuran at -78℃;

3,4'-Dichloropropiophenone (3946-29-0) → 5-chloro-1-indanone (42348-86-7)

Conditions	Yield
With aluminum (III) chloride; potassium chloride; sodium chloride at 130℃; for 3h; Temperature; Reagent/catalyst;	75%
With Et3NHCl-1.8AlCl3 ionic liquid In octane at 70 - 120℃; Ionic liquid;	72%
With sulfuric acid	70%

3,4'-Dichloropropiophenone (3946-29-0) + diethylamine (109-89-7) → β-(N,N-diethylamino)-p-chloropropiophenone hyrdochloride (5409-52-9)

Conditions	Yield
In tetrahydrofuran at 20℃; for 16h;	75%

3,4'-Dichloropropiophenone (3946-29-0) + diethylamine (109-89-7) → β-(N,N-diethylamino)-p-chloropropiophenone (54835-24-4)

Conditions	Yield
	75%

3,4'-Dichloropropiophenone (3946-29-0) + aniline (62-53-3) → 1-(4-chlorophenyl)-3-(phenylamino)propan-1-one (19832-75-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 30℃; for 3h;	72%
With triethylamine In tetrahydrofuran for 5h; Reflux;

3,4'-Dichloropropiophenone (3946-29-0) → (E)-1-(4-Chloro-phenyl)-3-[(E)-3-(4-chloro-phenyl)-3-oxo-propenylsulfanyl]-propenone (30031-54-0)

Conditions	Yield
With sodium sulfide In methanol at 20℃; for 0.5h;	70%

3,4'-Dichloropropiophenone (3946-29-0) + dimethyl propargylmalonate (107428-17-1) → dimethyl 2-(but-2-ynyl)-2-(3-(4-chlorophenyl)-3-oxopropyl)malonate (1357173-45-5)

Conditions	Yield
Stage #1: dimethyl propargylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 3,4'-Dichloropropiophenone With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 20℃; for 5h; Inert atmosphere; Reflux;	70%

methyl (+/-)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate (85929-61-9) + ethereal hydrogen chloride + 3,4'-Dichloropropiophenone (3946-29-0) → 1-(4-chlorophenyl)-3-(5,5-dimethyl-4-methoxycarbonyl-3-thiazolidinyl)propan-1-one (133914-23-5)

Conditions	Yield
With sodium acetate	64.9%

Upstream product

• 108-90-7 chlorobenzene 
• 625-36-5 2-chloropropionyl chloride 
• 74-85-1 ethene 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 113193-72-9 1-(4-chlorophenyl)-3-(1H-imidazol-1-yl)-1-propanone 
• 108664-81-9 3-(3-(4-chlorophenyl)-3-oxopropyl)quinazolin-4(3H)-one 
• 7448-87-5 p-chlorophenyl vinyl ketone 
• 65738-56-9 methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 144172-24-7 (R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester 
• 58824-54-7 p-chlorophenylvinylcarbinol 
• 861966-08-7 2-{1-[3-(4-chlorophenyl)-3-oxopropyl]piperidin-4-yl}pyridinium N-oxide 
• 861965-79-9 1-(4-chlorophenyl)-3-(4-pyridin-2-ylpiperidin-1-yl)propan-1-one 
• 861964-86-5 1-(4-chlorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one 
• 5409-52-9 β-(N,N-diethylamino)-p-chloropropiophenone hyrdochloride 
• 30412-07-8 1-(4-chlorophenyl)-3-(morpholin-1-yl)propane-1-one hydrochloride 
• 30031-54-0 (E)-1-(4-Chloro-phenyl)-3-[(E)-3-(4-chloro-phenyl)-3-oxo-propenylsulfanyl]-propenone 

Relevant academic research and scientific papers

New process for preparing 5-chloro-2,3-dihydro-1-indanone

The invention belongs to the technical field of preparation of farm chemical intermediates, and provides a preparation process of 5-chloro-2,3-dihydro-1-indanone. 3-chloropropionyl chloride and chlorobenzene are used as raw materials, mixed molten salt of aluminum trichloride, sodium chloride and zinc chloride is used as a catalyst, and the product 5-chloro-2,3-dihydro-1-indanone is prepared through a one-pot process reaction. According to the process, under the low temperature condition, the 3-chloropropionyl chloride and the chlorobenzene raw materials are directly dropwise added to the molten salt to carry out the liquid-liquid first-step reaction so as to easily disperse and contact the raw materials and the catalyst, and the stirring is uniform; and the liquid-liquid reaction can be realized at a relatively low temperature (130-135 DEG C) in the second-step reaction due to the relatively low molten temperature of the catalyst, so that side reactions are reduced, and the requirements on equipment and energy are reduced.

I2-Promoted Intramolecular Oxidative Cyclization of Butenyl Anilines: A Facile Route to Benzo[b]azepines

A metal-free approach for the synthesis of seven-membered N-heterocycles has been developed by the I2-promoted intramolecular cross-coupling/annulation of butenyl anilines. This cyclization reaction involves C?H activation and C?C bond formation and exhibits good functional group tolerance. A series of benzo[b]azepine derivatives are obtained in moderate to good yields.

Synthetic method of allyl alcohol derivatives

The invention discloses a synthetic method of allyl alcohol derivatives. The method comprises the following steps: reacting a compound 1C under the action of an iridium complex catalyst and bicarbonate of alkali metal; reacting with dialkyl dihydrosilane; and obtaining the allyl alcohol derivative 1A, wherein a reaction equation is shown in the specification; wherein R is selected from a fatty group or a substituted fatty group, an aromatic group or a substituted aromatic group, a substituent used for substitution contains C1-9 alkyl or heteroatom, the heteroatom contains any one or more of oxygen atom, halogen and nitrogen atom, and R1 and R2 are respectively selected from any one of methyl, ethyl, isopropyl or phenyl. According to the preparation method, a 3-chloropropionyl derivative 1Cis used for replacing an alpha-carbonyl alkene compound to react with bicarbonate of alkali metal and dialkyl dihydrosilane to obtain a target product. The method is low in raw material cost, rich insource, relatively stable in property, simple and convenient in synthetic route, environment-friendly, high in yield and suitable for industrial production.

5-chloro-2,3-dihydro-1-indanone preparation method

The invention provides a 5-chloro-2,3-dihydro-1-indanone preparation method, which comprises: carrying out a reaction by using chlorobenzene and 3-chloro-propionyl chloride as raw materials and usinga mixed molten salt as catalyst and a solvent to obtain 5-chloro-2,3-dihydro-1-indanone, wherein the mixed molten salt is a mixture comprising any two or three materials selected from potassium chloride, sodium chloride and aluminum chloride. According to the present invention, the mixed molten salt potassium chloride-sodium chloride-aluminum chloride is used as the catalyst, and becomes liquid ata temperature of about 100 DEG C, such that the problem that aluminum chloride is sublimated before melting is solved; and the mixed molten salt potassium chloride-sodium chloride-aluminum chloride is simultaneously used as the catalyst and the solvent in the reaction of chlorobenzene and 3-chloro-propionyl chloride, such that the conversion rate of the reaction can achieve 98% at the temperatureof 120-130 DEG C, and the yield of 5-chloro indanone can achieve 75%.

A production device for 5-chloro-indanone and a production method thereof

The present invention relates to a production device for 5-chloro-indanone, including an acrylic acid storage tank, at least two gas liquid reactors connected in series, a thionyl chloride storage tank, at least two first flow reactors connected in series, a 3-chloropropionyl chloride storage tank, a chlorobenzene storage tank, at least two second flow reactors connected in series, and at least two third flow reactors connected in series. A gas outlet of each first flow reactor is connected to a gas inlet of the gas liquid reactor at the rearmost end through a pipeline provided with a condenser. A feeding port of the second flow reactor in the front end is provided with a first aluminium chloride feeding device. A feeding port of the third flow reactor in the front end is provided with a second aluminium chloride feeding device. The invention relates to a method for producing the 5-chloro-indanone by utilizing the production device. The production device and method can achieve continuous cyclic production and a high product yield.

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

Improved preparation of 5-chloro-2-methoxycarbonyl-1-indanone for total synthesis of indoxacarb

5-Chloro-2-methoxycarbonyl-1-indanone 1 is an important intermediate for the synthesis of arthropodicidal oxadiazines indoxacarb. Here a convenient and environmentally friendly method with higher yield and low cost compared to existing method was developed. This method could be useful in manufacturing of indoxacarb, lowering the costs and avoiding excessive pollution.

Preparation, physical properties and n-type FET characteristics of substituted diindenopyrazinediones and bis(dicyanomethylene) derivatives

A series of halogen and alkyl substituted diindenopyrazinediones and bis(dicyanomethylene) derivatives have been synthesized as new n-type organic semiconductors based on nitrogen-containing heterocycles. Halogen groups were introduced to improve the electron injection. Their crystal structures and solid physical properties are discussed. Alkyl groups were introduced to increase the solubility in organic solvents. Furthermore, hexanoyl groups were introduced by oxidation of alkyl groups to increase the solubility and electron affinity. Dicyanomethylene groups were also introduced to further enhance the electron-accepting properties. Drop-cast as well as vapour deposited thin films showed n-type FET properties.

Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification

An enantioselective synthesis of chiral γ-azidoalcohols via lipase-catalyzed resolution is described. The efficiency of various lipases and the effect of different solvents have been studied. Pseudomonas cepacia immobilized on diatomaceous earth (PS-D) in n-hexane catalyzed the transesterification process in an efficient manner providing γ-azidoalcohols in high enantiomeric excess.