144172-24-7

Basic information

• Product Name: 5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone
• Synonyms: 5-chloro-2-hydroxy-1-indanone-2-carboxylic acid methyl ester;5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone;Methyl 5-chloro-2-hydroxy-1-indanone-2-carboxylate;methyl 5-chloro-2,3-dihydro-2-hydroxy-1-oxo-1h-indene-2-carboxylate;5-CHLORO-2,3-DIHYDRO-2-HYDROXY-1-1-OXO-1H-INDENE-2-CARBOXYLATE;5-Chlor-2-hydroxy-2-methoxycarbonyl-1-indanon;Methyl 5-chloro-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
• CAS NO: 144172-24-7
• Molecular Formula: C₁₁H₉ClO₄
• Molecular Weight: 240.63976
• Mol File: 144172-24-7.mol
• Article Data: 24

Chemical Properties

• Melting Point: 132-133 °C
• Boiling Point: 376.316oC at 760 mmHg
• Flash Point: 181.39oC
• Appearance: /
• Density: 1.503
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.616
• Solubility: Chloroform; DMSO; Ethyl Acetate
• PKA: 10.05±0.20(Predicted)
• CAS DataBase Reference: 5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone(144172-24-7)
• EPA Substance Registry System: 5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone(144172-24-7)

Safety Data

• Hazardous Substances Data: 144172-24-7(Hazardous Substances Data)

Usage

General Description

5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone is a chemical compound with the molecular formula C11H9ClO4. It is a white to beige solid powder with a molecular weight of 232.64 g/mol. 5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone is commonly used as a building block in organic synthesis and pharmaceutical research. It is known to exhibit antifungal properties and has been studied for its potential use in the development of new antifungal drugs. Additionally, it has also been investigated for its potential applications in the synthesis of various biologically active compounds and pharmaceutical intermediates. Overall, 5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone is a versatile compound with potential applications in both research and industrial settings.

InChI:InChI=1/C11H9ClO4/c1-16-10(14)11(15)5-6-4-7(12)2-3-8(6)9(11)13/h2-4,15H,5H2,1H3

Upstream product

• 65738-56-9 methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 42348-86-7 5-chloro-1-indanone 
• 3946-29-0 3,4'-Dichloropropiophenone 
• 108-90-7 chlorobenzene 
• 144172-26-9 5-chloro-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylic acid methyl ester 
• 616-38-6 carbonic acid dimethyl ester 
• 1866-38-2 3-chlorocinnamic acid 
• 21640-48-2 3-chlorohydrocinnamic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 144172-26-9 5-chloro-1-hydrazono-2-hydroxy-indan-2-carboxylic acid methyl ester 
• 144172-26-9 5-chloro-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylic acid methyl ester 
• 170917-89-2 7?chloro-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine?2,4a-dicarboxylic acid 4a-methyl 2?benzyl ester 
• 173903-19-0 C₁₉H₁₇ClN₂O₅ 

Relevant articles and documents

Visible Light-Induced Salan-Copper(II)-Catalyzed Enantioselective Aerobic α-Hydroxylation of β-Keto Esters

A strategy of visible light-induced salan-copper(II)-catalyzed asymmetric α-hydroxylation of β-keto ester with utilization of sustainable air as the oxidant was developed. This protocol allows convenient access to a number of enantioenriched α-hydroxyl β-keto esters (up to 95% yield, 96% ee), especially for β-keto methyl esters that are valuable architectures in pharmaceuticals, including the key intermediate of the sodium-channel blocker (S)-indoxacarb. Experimental studies suggest that reactive singlet oxygen may participate in this reaction. (Figure presented.).

Design, synthesis and structure-activity relationship of indoxacarb analogs as voltage-gated sodium channel blocker

Indoxacarb, the first commercialized pyrazoline-type sodium-channel blocker, is a commonly used insecticide because of high selectivity. To discover sodium-channel blocker with high insecticidal activity, a series of novel indoxacarb analogs were designed and synthesized by judicious structural modifications of the substituent group of C5, C6 in indenone and C′4 in benzene ring. Some analogs exhibited significant insecticidal activities against Spodoptera litura F. and excellent BgNav1-1a channel inhibitory activity. The structure-activity analysis indicated that the presence of strong electron-withdrawing group and decreased steric hindrance of indenone ring (R1, R2) in 5- and 6-position could enhance larvicidal activity and BgNav1-1a channel inhibitory activity.

Discovery of a Novel Series of Tricyclic Oxadiazine 4a-Methyl Esters Based on Indoxacarb as Potential Sodium Channel Blocker/Modulator Insecticides

Indoxacarb, a commercialized oxadiazine insecticide, nearly irreversibly blocks open/inactivated, but not resting sodium channels. The structure-activity relationships showed that the substituents at the position of the chiral atom in the oxadiazine ring are very important to the biological activity of oxadiazine insecticide. Here we synthesized a series of tricyclic oxadiazine 4a-methyl ester derivatives. The chiral atom in the oxadiazine ring has been epimerized and substituted with either pyrethric acid or cinnamic acid derivatives. Benzene ring in the tricyclic moiety was substituted with a chlorine, fluorine, or bromine atom, and nitrogen-linked benzene ring was substituted with a trifluoromethyl or trifluoromethoxy group. Toxicity of these compounds against Spodoptera litura F. was evaluated. Diastereoisomers of most toxic compounds J7 and J9 with pyrethric acid moiety were separated by flash column chromatography. The more polar diastereoisomers, J7-L-Rf and J9-L-Rf, and compounds J24 and J26 with cinnamic acid moiety exhibited highest insecticidal activities. We further used Monte Carlo energy minimizations to dock compound J7 and J24 in the NavMs-based homology model of the open cockroach sodium channel. In the low-energy binding modes, the compound interacted with residues in the inner pore and domain interfaces, which previously were proposed to contribute to receptors of pyrethroids and sodium channel blocker insecticides. Our results define compound J7 and J24 as a potentially useful optimized hit for the development of multiple sites sodium channel blocker or modulator.

Synthesis method of alpha-hydroxy-beta-keto ester compound

The invention relates to the field of organic synthesis, and discloses a synthesis method of an alpha-hydroxy-beta-keto ester compound, the synthesis method comprises the following steps: placing a beta-keto ester compound in an organic solvent, adding a complex catalyst and a photosensitizer, and carrying out an alpha-hydroxylation reaction by taking visible light as a driving force and air as an oxidizing agent, and after the reaction is finished, carrying out post-treatment on the reaction liquid to obtain the alpha-hydroxy-beta-keto ester compound. The synthesis method is efficient, mild, high in yield, green, environmentally friendly, wide in reaction substrate range and extremely low in photosensitizer catalytic amount, meanwhile the prepared product can serve as an important organic intermediate to be applied to the fields of medicine, pesticide and the like and has important application value.

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.