3946-29-0

Basic information

• Product Name: 3,4'-Dichloropropiophenone
• Synonyms: (2-CHLOROETHYL)-4-CHLOROPHENYLKETONE;3,4'-DICHLOROPROPIONPHENONE;3',4-DICHLOROPROPIOPHENONE;3,4'-DICHLOROPROPIOPHENONE;3-CHLORO-1-(4-CHLOROPHENYL)-1-OXOPROPANE;3-CHLORO-1-(4-CHLOROPHENYL)PROPAN-1-ONE;BETA,4-DICHLOROPROPIOPHENONE;CHEMPACIFIC 42352
• CAS NO: 3946-29-0
• Molecular Formula: C₉H₈Cl₂O
• Molecular Weight: 203.07
• EINECS: 223-537-4
• Product Categories: Acetophenone Series;C9;Carbonyl Compounds;Ketones
• Mol File: 3946-29-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 48-51 °C(lit.)
• Boiling Point: 135-137 °C0.6 mm Hg(lit.)
• Flash Point: 178 °F
• Appearance: yellow to brown crystals or crystalline powder
• Density: 1.2568 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• BRN: 1866915
• CAS DataBase Reference: 3,4'-Dichloropropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4'-Dichloropropiophenone(3946-29-0)
• EPA Substance Registry System: 3,4'-Dichloropropiophenone(3946-29-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37-36/37/38
• Safety Statements: 23-26-27-36/37/39-45-37/39
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3946-29-0(Hazardous Substances Data)

Usage

Chemical Properties

yellow to brown crystals or crystalline powder

Uses

3’,4’-Dichloropropiophenone is used as a reagent in the preparation of antidepressant aryl-alkyl-piperidine derivatives. Also used in the synthesis of mGlu5 receptor negative allosteric modulators. Also in the genetic screening of compounds countering the growth of methylthioadenosine phosphorylase involved in cancer spread.

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

• 112031-92-2 N-<3-oxo-3-(4-chlorophenyl)propyl>phthalimide 
• 113193-72-9 1-(4-chlorophenyl)-3-(1H-imidazol-1-yl)-1-propanone 
• 7448-87-5 p-chlorophenyl vinyl ketone 
• 42348-86-7 5-chloro-1-indanone 
• 25574-18-9 3-chloro-1-(4-chlorophenyl)propan-1-ol 
• 30031-54-0 (E)-1-(4-Chloro-phenyl)-3-[(E)-3-(4-chloro-phenyl)-3-oxo-propenylsulfanyl]-propenone 
• 861965-79-9 1-(4-chlorophenyl)-3-(4-pyridin-2-ylpiperidin-1-yl)propan-1-one 
• 861966-08-7 2-{1-[3-(4-chlorophenyl)-3-oxopropyl]piperidin-4-yl}pyridinium N-oxide 
• 688360-42-1 1-chloro-4-(1,1-dimethoxy-3-nitro-propyl)-benzene 
• 688360-50-1 (1R,6R,8R)-6-(4-chloro-phenyl)-2-oxo-7,9-dioxa-3-aza-bicyclo[4.2.1]nonane-8-carboxylic acid methyl ester 
• 688360-45-4 (4R,5R)-2-(4-chloro-phenyl)-2-(2-nitro-ethyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 60868-02-2 1-(4-chloro-phenyl)-3-(4-methyl-piperazin-1-yl)-propan-1-one 
• 133914-13-3 1-(4-chlorophenyl)-3-(5,5-dimethyl-4-ethoxycarbonyl-3-thiazolidinyl)propan-1-one 
• 950650-35-8 C₉H₈ClN₃O 

Relevant articles and documents

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.

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.

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.