35112-28-8

Usage

Uses

Used in Chemical Synthesis:
METHYL 2,4-DICHLOROBENZOATE is used as an intermediate in the synthesis of various organic compounds, including 2,4-dichloro-benzohydroxamic acid. Its unique structural features make it a valuable building block for the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 2,4-DICHLOROBENZOATE may be utilized as a starting material for the synthesis of novel drug candidates. Its halogenated aromatic structure can be further modified to create compounds with specific biological activities, targeting various therapeutic areas.
Used in Agrochemical Industry:
METHYL 2,4-DICHLOROBENZOATE can also be employed in the agrochemical industry for the development of new pesticides or herbicides. Its chemical properties may allow for the creation of compounds with enhanced efficacy and selectivity, contributing to more effective and environmentally friendly agricultural practices.
Used in Dye and Pigment Industry:
The halogenated aromatic structure of METHYL 2,4-DICHLOROBENZOATE makes it a potential candidate for use in the dye and pigment industry. It can be used as a precursor to synthesize new dyes or pigments with improved color properties and stability.
Used in Material Science:
In the field of material science, METHYL 2,4-DICHLOROBENZOATE may find applications in the development of new polymers or coatings with specific properties, such as enhanced durability, UV resistance, or self-healing capabilities. Its unique structure can be exploited to create materials with tailored characteristics for various applications.

InChI:InChI=1/C8H6Cl2O2/c1-12-8(11)6-3-2-5(9)4-7(6)10/h2-4H,1H3

Upstream product

• 110-91-8 morpholine 
• 50-84-0 2,4 dichlorobenzoic acid 
• 17287-03-5 trimethylsulphonium hydroxide 
• 74-88-4 methyl iodide 
• 107-06-2 1,2-dichloro-ethane 
• 67-56-1 methanol 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 705254-34-8 potassium trifluoro(4-(methoxycarbonyl)phenyl)borate 
• 90532-34-6 1,3-dichloro-4-(methoxymethyl)benzene 
• 89-75-8 2,4-dichlorobenzoyl chloride 
• 4731-65-1 tris(o-methoxyphenyl)phosphine 
• 13014-18-1 2,4-dichlorobenzotrichloride 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 188065-31-8 2,4-dichloro-1-{[(2,4-dichlorobenzyl)disulfanyl]methyl}benzene 

Downstream Products

• 81450-58-0 5-(2,4-Dichloro-phenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol 
• 2459-10-1 benzene-1,2,4-tricarboxylic acid trimethyl ester 
• 56882-51-0 5-(2,4-dichlorophenyl)-2,3,5,6-tetrahydroimidazo[2,1-a]isoquinolin-5-ol 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 94171-11-6 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)ethanone 
• 1178849-91-6 1-(2,4-Dichlorophenyl)-2-(4-methoxyphenyl)ethanone 
• 889946-21-8 3-((5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl)thio)propanoic acid 
• 168893-49-0 5-(2,4-dichlorophenyl)-4H-1,2,4-triazol-3-amine 
• 183368-35-6 2-(chloromethyl)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole 
• 23767-45-5 5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-ol 
• 19861-63-3 5-amino-2,4-dichlorobenzoic acid 

Relevant academic research and scientific papers

Synthesis and antibacterial activity of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives

By introducing the pyridinium group into 2,5-substituted-1,3,4-oxadiazole, a series of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives were obtained, and their antibacterial activities were evaluated via turbidimeter test in vitro. The bioassays reveal that most of the target compounds exhibit better inhibition activities against pathogen Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri than positive controls bismerthiazol (CK1) or thiodiazole copper (CK2). Among them, I-8, I-10, I-12, II-10, II-12, III-10, and III-12 exert excellent inhibition activities against the three pathogenic bacteria with the half-maximal effective concentration (EC50) values ranging from 0.54 to 12.14 μg/mL. Our results demonstrate that pyridinium-tailored 1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives can serve as potential alternative bactericides for the management of plant bacterial diseases.

Visible-light-induced selective aerobic oxidation of sp3 C-H bonds catalyzed by a heterogeneous AgI/BiVO4 catalyst

An efficient oxidation of sp3 C-H bonds to esters and ketones has been developed using AgI/BiVO4 as the photocatalyst and O2 as the oxidant in water. Various substrates can be transformed into the desired esters and ketones in moderate to good yields. The synthetic utility of this approach has been demonstrated by gram-level experiments and consecutive oxidation experiments. A plausible mechanism has been proposed.

Synthesis, biological evaluation of benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents

Twenty benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety were synthesized and evaluated for their anti-oxidant and anti-inflammatory activities. Among these compounds, 8h and 8l were appeared to have high radical scavenging efficacies as 0.05 ± 0.02 and 0.07 ± 0.03 mmol/L of IC50 values in ABTS+[rad] bioassay, respectively. In anti-inflammatory tests, compound 8h displayed good activity with 57.35% inhibition after intraperitoneal administration, which was more potent than the reference drug (indomethacin). Molecular modeling studies were performed to investigate the binding mode of the representative compound 8h into COX-2 enzyme. In vitro enzyme study implied that compound 8h exerted its anti-inflammatory activity through COX-2 inhibition.

Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides

A transition metal- and organophotocatalyst free synthesis of esters, carboxylic anhydrides and amides from aldehydes induced by visible-light has been reported. The proposed methodology can be carried out by the use of sunlight or artificial visible light as a blue LED source. The methodology has a very broad applicability and the desired products are obtained in very satisfactory yields.

Synthesis and biological activities of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety

A series of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety were designed, synthesized and evaluated for their antibacterial, antifungal and antiviral activities. The bioassay results indicated that most of target compounds showed good antiviral activities against tobacco mosaic virus (TMV) and antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). Especially, the anti-Xoo effect of title compounds 5k (N-(5-methoxybenzo[d]thiazol-2-yl)-2-((5-(2-tolyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) and the anti-Rs effect of title compounds 5a (N-(5-nitrobenzo[d]thiazol-2-yl)-2-((5-(4-(trifluorom ethyl)phenyl)-1,3,4-thiadiazol-2-yl)thio)acetmide) respectively reached 52.4% and 71.6% at 100 μg/mL, which are superior to that of bismerthiazol (32.0% and 52.3%). In addition, the protective and inactivation activities of title compound 5i (N-(5-methoxybenzo [d]thiazol-2-yl)-2-((5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) against TMV were 79.5% and 88.3%, respectively, which are better than that of ningnanmycin (76.4% and 86.8%). The above research showed that benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety may be used as potential molecular templates in searching for highly-efficient antiviral and antibacterial agents.

Synthesis of Thiazolium-Labeled 1,3,4-Oxadiazole Thioethers as Prospective Antimicrobials: In Vitro and in Vivo Bioactivity and Mechanism of Action

In this study, a type of thiazolium-labeled 1,3,4-oxadiazole thioether bridged by diverse alkyl chain lengths was constructed. The antimicrobial activity of the fabricated thioether toward plant pathogenic bacteria and fungi was then screened. Antibacterial evaluation indicated that title compounds possess specific characteristics that enable them to severely attack three phytopathogens, namely, Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri with minimal EC50 values of 0.10, 3.27, and 3.50 μg/mL, respectively. Three-dimensional quantitative structure-activity relationship models were established to direct the following excogitation for exploring higher active drugs. The in vivo study against plant bacterial diseases further identified the prospective application of title compounds as alternative antibacterial agents. The proteomic technique, scanning electron microscopy patterns, and fluorescence spectrometry were exploited to investigate the antibacterial mechanism. Additionally, some target compounds performed superior inhibitory actions against three tested fungal strains. In view of their simple molecular architecture and highly efficient bioactivity, these substrates could be further explored as promising surrogates for fighting against plant microbial infections.

Rational Optimization and Action Mechanism of Novel Imidazole (or Imidazolium)-Labeled 1,3,4-Oxadiazole Thioethers as Promising Antibacterial Agents against Plant Bacterial Diseases

The emergence and widespread occurrence of plant bacterial diseases that cause global production constraints have become major challenges to agriculture worldwide. To promote the discovery and development of new bactericides, imidazole-labeled 1,3,4-oxadiazole thioethers were first fabricated by integrating the crucially bioactive scaffolds of the imidazole motif and 1,3,4-oxadiazole skeleton in a single molecular architecture. Subsequently, a superior antibacterial compound A6 was gradually discovered possessing excellent competence against plant pathogens Xanthomonas oryzae pv oryzae and Xanthomonas axonopodis pv citri with EC50 values of 0.734 and 1.79 μg/mL, respectively. These values were better than those of commercial agents bismerthiazol (92.6 μg/mL) and thiodiazole copper (77.0 μg/mL). Further modifying the imidazole moiety into the imidazolium scaffold led to the discovery of an array of potent antibacterial compounds providing the corresponding minimum EC50 values of 0.295 and 0.607 μg/mL against the two strains. Moreover, a plausible action mechanism for attacking pathogens was proposed based on the concentration dependence of scanning electron microscopy, transmission electron microscopy, and fluorescence microscopy images. Given the simple molecular structures, easy synthetic procedure, and highly efficient bioactivity, imidazole (or imidazolium)-labeled 1,3,4-oxadiazole thioethers can be further explored and developed as promising indicators for the development of commercial drugs.

5-Aryl-1,3,4-oxadiazol-2-ylthioalkanoic Acids: A Highly Potent New Class of Inhibitors of Rho/Myocardin-Related Transcription Factor (MRTF)/Serum Response Factor (SRF)-Mediated Gene Transcription as Potential Antifibrotic Agents for Scleroderma

Through a phenotypic high-throughput screen using a serum response element luciferase promoter, we identified a novel 5-aryl-1,3,4-oxadiazol-2-ylthiopropionic acid lead inhibitor of Rho/myocardin-related transcription factor (MRTF)/serum response factor (SRF)-mediated gene transcription with good potency (IC50 = 180 nM). We were able to rapidly improve the cellular potency by 5 orders of magnitude guided by sharply defined and synergistic SAR. The remarkable potency and depth of the SAR, as well as the relatively low molecular weight of the series, suggests, but does not prove, that binding to the unknown molecular target may be occurring through a covalent mechanism. The series nevertheless has no observable cytotoxicity up to 100 μM. Ensuing pharmacokinetic optimization resulted in the development of two potent and orally bioavailable anti-fibrotic agents that were capable of dose-dependently reducing connective tissue growth factor gene expression in vitro as well as significantly reducing the development of bleomycin-induced dermal fibrosis in mice in vivo.

Discovery of Allosteric, Potent, Subtype Selective, and Peripherally Restricted TrkA Kinase Inhibitors

Tropomyosin receptor kinases (TrkA, TrkB, TrkC) are activated by hormones of the neurotrophin family: nerve growth factor (NGF), brain derived neurotrophic factor (BDNF), neurotrophin 3 (NT3), and neurotrophin 4 (NT4). Moreover, the NGF antibody tanezumab has provided clinical proof of concept for inhibition of the TrkA kinase pathway in pain leading to significant interest in the development of small molecule inhibitors of TrkA. However, achieving TrkA subtype selectivity over TrkB and TrkC via a Type I and Type II inhibitor binding mode has proven challenging and Type III or Type IV allosteric inhibitors may present a more promising selectivity design approach. Furthermore, TrkA inhibitors with minimal brain availability are required to deliver an appropriate safety profile. Herein, we describe the discovery of a highly potent, subtype selective, peripherally restricted, efficacious, and well-tolerated series of allosteric TrkA inhibitors that culminated in the delivery of candidate quality compound 23.

Direct oxidation of aldehydes to methyl esters with urea hydrogen peroxide and p-toluenesulfonyl chloride

Combination of urea hydrogen peroxide and p-toluenesulfonyl chloride in methanol was proved to be facile and highly efficient for the oxidative methyl esterification of various aldehydes to the corresponding carboxylic methyl esters.