21640-48-2

Usage

Chemical Properties

White to brown powder

InChI:InChI=1/C9H9ClO2/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6H,4-5H2,(H,11,12)

Upstream product

• 1866-38-2 3-chlorocinnamic acid 
• 683215-19-2 2-(3-chlorobenzyl)malonic acid 
• 108-41-8 1-chloro-3-methylbenzene 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 625-99-0 3-iodochlorobenzene 
• 802294-64-0 propionic acid 
• 141-82-2 malonic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 124-38-9 carbon dioxide 
• 2039-85-2 3-Chlorostyrene 
• 1664-56-8 m-aminocinnamic acid 
• 7116-35-0 ethyl 3-(3-chlorophenyl)propanoate 
• 70146-77-9 [(3-chlorophenyl)methyl]propanedioic acid dirthyl ester 

Downstream Products

• 103040-43-3 3-(3-chlorophenyl)propionic acid methyl ester 
• 1159704-74-1 N-[5-chloro-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-3-(3-chloro-phenyl)-propionamide 
• 144172-24-7 (R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester 
• 144172-26-9 5-chloro-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylic acid methyl ester 
• 13078-79-0 2-(3-chlorophenyl)ethylamine 
• 40478-50-0 3-(3-chlorophenyl)propionyl chloride 

Relevant academic research and scientific papers

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.

Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins

The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.

Cyclohexyl-Fused, Spirobiindane-Derived, Phosphine-Catalyzed Synthesis of Tricyclic ?3-Lactams and Kinetic Resolution of ?3-Substituted Allenoates

A C2-symmetric chiral phosphine catalyst, NUSIOC-Phos, which can be easily derived from cyclohexyl-fused spirobiindane, was introduced. A highly enantioselective domino process involving pyrrolidine-2,3-diones and γ-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic γ-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic γ-substituted allenoates was developed for the generation of optically enriched chiral allenoates.

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.

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.

Ligand-Controlled Regioselective Hydrocarboxylation of Styrenes with CO2 by Combining Visible Light and Nickel Catalysis

The ligand-controlled Markovnikov and anti-Markovnikov hydrocarboxylation of styrenes with atmospheric pressure of CO2 at room temperature using dual visible-light-nickel catalysis has been developed. In the presence of neocuproine as ligand, the Markovnikov product is obtained exclusively, while employing 1,4-bis(diphenylphosphino)butane (dppb) as the ligand favors the formation of the anti-Markovnikov product. A range of functional groups and electron-poor, -neutral, as well as electron-rich styrene derivatives are tolerated by the reaction, providing the desired products in moderate to good yields. Preliminary mechanistic investigations indicate the generation of a nickel hydride (H-NiII) intermediate, which subsequently adds irreversibly to styrenes.

Pd-Catalyzed β-C(sp3)?H Arylation of Propionic Acid and Related Aliphatic Acids

A generally applicable Pd-catalyzed protocol for the β-C(sp3)?H arylation of propionic acid and related α-branched aliphatic acids is reported. Enabled by the use of N-acetyl-β-alanine as ligand our protocol delivers a broad range of arylation products. Notably, the highly challenging substrate, propionic acid, which lacks any acceleration through the Thorpe–Ingold effect, can be employed as substrate with synthetically useful yields. Furthermore, the scalability and synthetic applicability of the protocol are demonstrated.

Direct β-Selective Hydrocarboxylation of Styrenes with CO2 Enabled by Continuous Flow Photoredox Catalysis

The direct β-selective hydrocarboxylation of styrenes under atmospheric pressure of CO2 has been developed using photoredox catalysis in continuous flow. The scope of this methodology was demonstrated with a range of functionalized terminal styrenes, as well as α-substituted and β-substituted styrenes.

Copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids using (trifluoromethyl)trimethylsilane

Trifluoromethylated acetylenes and arenes are widely applicable in the synthesis of pharmaceuticals and agrochemicals. In 2010, our group has reported the copper-mediated oxidative trifluomethylation of terminal alkynes and aryl boronic acids. This method allows a wide range of functional group tolerant trifluoromethylated acetylenes and arenes to be easily prepared. After the preliminary mechanistic studies of the oxidative trifluoromethylation of terminal alkyne, an efficient copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids has been developed. The catalytic protocol is successfully achieved by adding both the substrate and a portion of CF3TMS slowly using a syringe pump to the reaction mixture.

Samarium diiodide reduction of cinnamic acids

The method for measuring SmI2 reduction rates is expanded to a wider range of organic compounds by using not only GC or GC/MS, but also HPLC as the detecting tool. The reduced substrates are not only confined to water insoluble compounds or low boiling compounds only. Water soluble cinnamic acid derivatives of high boiling points are chosen for this application. The absolute rate constants of SmI2 reduction of cinnamic acid in the presence of hexamethyl phosphoramide or t-butanol is considered as a suitable proton source in this reaction. The rates are dependent on substrates and additives as: Rate · [t-BuOH][Cinnamic acid] and Rate · [HMPA][Cinnamic acid] The reduction rates of α-methylcinnamic acid, 2-methylcinnamic acid, 4-methylcinnamic acid, 2-methoxycinnamic acid, 3-methoxycinnamic acid, 4-methoxycinnamic acid, 2-hydroxycinnamic acid, 3-hydroxycinnamic acid, 4-hydroxycinnamic acid, 2-chlorocinnamic acid, 3-chlorocinnamic acid, 4-chlorocinnamic acid were carefully measured to study the substituent effect.