42348-86-7

Usage

Uses

Used in Pesticide Industry:
5-Chloro-1-indanone is used as an important intermediate in the production of DuPont's new variety of pesticides, specifically indoxacarb (popular name: indoxacarb). Its role in this industry is crucial for the development of effective pest control solutions.
Used in Pharmaceutical Industry:
5-Chloro-1-indanone serves as a vital intermediate in the synthesis of various medicines. It is used in the preparation of 5-chloro-2-methoxycarbonyl-1-indanone, which is a starting reagent for the synthesis of important biomedical compounds such as anticonvulsants, anticholinergics, and diarylsulfonylureas. These compounds have potential activity against solid tumors, making 5-Chloro-1-indanone a valuable component in the development of novel therapeutic agents.
Used in Organic Synthesis:
5-Chloro-1-indanone participates in Irie's synthesis of substituted pyridines, which are essential building blocks in the creation of various organic compounds with diverse applications in different industries, including pharmaceuticals, agrochemicals, and materials science.

Preparation

3-chlorobenzaldehyde as raw material first reacts with propionic acid to prepare 3-chloro-phenylpropionic acid, which is then subjected to Friedel-Crafts acylation reaction to prepare 5-chloro-1-indanone. Organic solvents of formic acid diethylamine participate in the first step, and the reaction temperature is 20-150℃. An organic solvent of methylene chloride and a catalyst of zinc chloride participate in the second step, and the reaction temperature is -10 to 80 ℃. Synthetic method of 5-chloro-1-indanone

InChI:InChI=1/C9H7ClO/c10-7-2-3-8-6(5-7)1-4-9(8)11/h2-3,5H,1,4H2

Upstream product

• 3946-29-0 3,4'-Dichloropropiophenone 
• 40478-50-0 3-(3-chlorophenyl)propionyl chloride 
• 33781-38-3 5-chloro-2,3-dihydro-1H-inden-1-ol 
• 42175-03-1 methyl ester of m-chlorocinnamic acid 
• 103040-43-3 3-(3-chlorophenyl)propionic acid methyl ester 
• 1866-38-2 3-chlorocinnamic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 7448-87-5 p-chlorophenyl vinyl ketone 
• 108-90-7 chlorobenzene 
• 625-36-5 2-chloropropionyl chloride 
• 7116-35-0 ethyl 3-(3-chlorophenyl)propanoate 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 826-65-3 endo-tricyclo<5.2.1.0^2,6>deca-4,8-dien-3,10-dione 
• 21640-48-2 3-chlorohydrocinnamic acid 

Downstream Products

• 77948-80-2 5-chloro-1-phenyl-1-indanol 
• 33781-38-3 5-chloro-2,3-dihydro-1H-inden-1-ol 
• 65738-56-9 methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 77948-79-9 5-chloro-2-benzoylphenylacetic acid 
• 126827-59-6 6-chloro-1-phenylisochroman-3-one 
• 126812-65-5 2-[5-Chloro-2-(hydroxy-phenyl-methyl)-phenyl]-acetamide 
• 20373-10-8 2-benzyl-5-chlorophenylacetic acid 
• 77948-78-8 6-chloro-3-phenyl-1H-indene 
• 54714-53-3 2-bromo-5-chloro-1-indanone 
• 351528-73-9 5'-chloro-2',3'-dihydrospiro[imidazolidine-4,1'-indene]-2,5-dione 
• 118259-88-4 5-chloro-2,2-dimethyl-1-indanone 
• 67120-39-2 5-chloro-2,3-dihydro-1H-inden-1-ylamine 
• 501335-21-3 2-benzyl-5-chloro-2,3-dihydro-1H-inden-1-one 
• 1160053-93-9 5-chloro-2-(4-nitrobenzyl)-2,3-dihydro-1H-inden-1-one 

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.

Synthesis method of 5-chloro-1-indanone

The invention relates to a synthesis method of 5-chloro-1-indanone, and belongs to the technical field of organic synthesis. According to the invention, 1-(4-chlorphenyl)-2-propylene-1-ketone is used as a raw material, and under the catalysis of hydrogen chloride, intramolecular cyclization is carried out to generate 5-chloro-1-indanone. The hydrogen chloride gas is used for replacing aluminum trichloride catalysis in a traditional process, the low-temperature process is used for replacing the high-temperature process, the risk that aluminum trichloride possibly explodes when encountering water under the high-temperature condition is avoided, and essential safety of the process is achieved. Besides, the synthesis method only generates a small amount of acid-base neutralization wastewater, so that the environmental protection benefit is greatly improved.

Preparation method for synthesizing 5-chloro-1-indanone through one-step method

The invention provides a preparation method for synthesizing 5-chloro-1-indanone by a one-step method, wherein the preparation method comprises the following steps: mixing chlorobenzene, perfluoro tert-butyl alcohol and a catalyst macroporous strongly acidic resin, slowly dropwise adding 3-chloropropionyl chloride under the protection of nitrogen, reacting for a period of time at a certain temperature, filtering out a catalyst, and evaporating out the perfluoro tert-butyl alcohol at normal pressure; and adding dichloromethane and an HCl solution, separating out an oil layer, washing with a NaHCO3 aqueous solution until the oil layer is neutral, evaporating out dichloromethane at normal pressure, recrystallizing, and drying in vacuum to obtain the 5-chloro-1-indanone. The preparation method has the following technical effects: 1) 5-chloro-1-indanone is synthesized by a one-step method by adopting a reaction route of taking 3-chloropropionyl chloride and chlorobenzene as raw materials, taking perfluoro tert-butyl alcohol as a solvent and taking strong acid macroporous resin as a catalyst. The solvent and the catalyst in the method can be recycled and reused, and the method is environment-friendly, simple in process, high in yield and low in cost.

Preparation method of 5-chloro-1-indanone

The invention provides a preparation method of 5-chloro-1-indanone, and belongs to the technical field of organic synthesis. Chlorobenzene and 3-chloropropionyl chloride are used as raw materials, mixed molten salt and heteropolyacid are used as catalysts, and heating reaction is performed to obtain 5-chloro-1-ndanone, wherein the heteropolyacid is SiO2 loaded phosphotungstic acid, and the mixed molten salt is a mixture of any two or three of potassium chloride, sodium chloride and aluminum chloride. By controlling the feeding temperature and the feeding sequence, the reaction is carried out at a lower temperature, the problems of large solid amount, high temperature, violent reaction, large tar amount, carbonization of raw materials, more three wastes and the like when aluminum trichloride is used as a catalyst are avoided, and the yield of 5-chloro-1-indanone can reach up to 85%.

Synthesis process of indoxacarb

The invention discloses a synthesis process of indoxacarb. The method comprises the following steps: reacting m-chlorobenzaldehyde serving as a raw material with malonic acid to remove monomolecular water and carbon dioxide to generate an intermediate SRCA, performing a hydrogenation reduction on the intermediate SRCA in an autoclave in the presence of a catalyst to obtain an intermediate SRCH, and cyclizing the SRCH by using hydrogen fluoride as a dehydrating agent to obtain the final product indoxacarb. The synthesis process is simple and easy to implement, energy is saved, consumption is reduced, the yield is increased, and good economic and environmental benefits are obtained.

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.

Preparation method for indanone compound

The invention especially relates to a preparation method for an indanone compound, belonging to the field of organic synthesis. The preparation method for the indanone compounds comprises the following steps: 1) subjecting a compound as shown in a formula I and a compound as shown in a formula II to a condensation reaction so as to prepare a compound as shown in a formula III; 2) subjecting the compound as shown in the formula III to hydrolysis in the presence of alkali so as to prepare a compound as shown in a formula IV; and 3) carrying out acylation and ring closure on the compound as shownin the formula IV so as to prepare the as shown in a formula V. Compared with the prior art, the preparation method for the indanone compound in the invention has the advantages of low raw material cost, simple operation, low production of waste water, waste gas and industrial residues, high yield and the like, and is more suitable for industrial production; and compared with various traditionalpreparation methods for the indanone compound, the preparation method of the invention has obvious advantages and shows good industrialization prospects.

Benzo cyclic ketone compound preparation method

The invention discloses a benzo cyclic ketone compound preparation method, which specifically comprises: adding a phenyl acyl chloride compound into a solvent hexafluoroisopropanol in a dropwise manner, and under the catalytic effect of a catalyst Lewis acid (aluminum trichloride or iron trichloride), carrying out a reaction at a temperature of 0-59 DEG C until the acyl chloride is completely converted so as to obtain the benzo cyclic ketone compound. According to the present invention, the benzo cyclic ketone compound is prepared through the cyclization reaction by using the hexafluoroisopropanol as the solvent, such that the use of a large amount of Lewis acid or strong protic acid is avoided so as to substantially reduce the generation of three wastes and provide the less corrosivenessto the equipment; and the method of the present invention is environmentally friendly and safe, and has good economical benefits.

A new 5 - chloro -1 - indenone synthetic method

The invention discloses a synthetic method of 5-chloro-1-indanone, and belongs to the field of organic synthesis. 3-chlorobenzaldehyde as raw material first reacts with propionic acid to prepare 3-chloro-phenylpropionic acid, which is then subjected to Friedel-Crafts acylation reaction to prepare 5-chloro-1-indanone. Organic solvents of formic acid diethylamine participate in the first step, and the reaction temperature is 20-150 DEG C. An organic solvent of methylene chloride and a catalyst of zinc chloride participate in the second step, and the reaction temperature is -10 to 80 DEG C. The synthesis process of 5-chloro-1-indanone provided by the invention is simple and easy for magnification, resolves the technical problems of in the presence of long synthetic route, expensive catalysts or raw materials, harsh reaction conditions and high cost in the current synthetic method; particularly in the environment, compared with the conventional synthetic method of 5-chloro-1-indanone process, the method provided by the invention avoids environmental pollution problem caused by strong acid and treatment of a large amount of wastewater.