56882-52-1

Basic information

• Product Name: ETHYL 2,4-DICHLOROBENZOATE
• Synonyms: RARECHEM AL BI 0019;ETHYL 2,4-DICHLOROBENZOATE;Benzoic acid, 2,4-dichloro-, ethyl ester
• CAS NO: 56882-52-1
• Molecular Formula: C₉H₈Cl₂O₂
• Molecular Weight: 219.06
• Mol File: 56882-52-1.mol

Chemical Properties

• Boiling Point: 272.8 °C at 760 mmHg
• Flash Point: 111.8 °C
• Appearance: /
• Density: 1.305 g/cm³
• Vapor Pressure: 0.00595mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: ETHYL 2,4-DICHLOROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,4-DICHLOROBENZOATE(56882-52-1)
• EPA Substance Registry System: ETHYL 2,4-DICHLOROBENZOATE(56882-52-1)

Safety Data

• Hazardous Substances Data: 56882-52-1(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Ethyl 2,4-dichlorobenzoate is used as a selective herbicide for controlling specific types of unwanted plant growth while remaining safe for other plants. It is incorporated into commercial products to manage weeds and protect crops.
Used in Industrial Applications:
In industrial settings, Ethyl 2,4-dichlorobenzoate is utilized for controlling plant growth in areas such as storage facilities, manufacturing plants, and other areas where unwanted vegetation can pose a risk or hinder operations.
It is crucial to handle Ethyl 2,4-dichlorobenzoate with care and adhere to safety guidelines to ensure its safe and effective use in these applications.

InChI:InChI=1/C9H8Cl2O2/c1-2-13-9(12)7-4-3-6(10)5-8(7)11/h3-5H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 89-75-8 2,4-dichlorobenzoyl chloride 
• 141-52-6 sodium ethanolate 
• 50-84-0 2,4 dichlorobenzoic acid 
• 874-42-0 2,4-dichlorobenzaldeyhde 

Downstream Products

• 104517-04-6 2,4-dichloro-1-(prop-1-en-2-yl)benzene 
• 5814-06-2 2,4-dichlorobenzohydrazide 
• 50-84-0 2,4 dichlorobenzoic acid 
• 56882-51-0 5-(2,4-dichlorophenyl)-2,3,5,6-tetrahydroimidazo[2,1-a]isoquinolin-5-ol 
• 35112-28-8 methyl 2,4-dichlorobenzoate 
• 39528-61-5 3-(2',4'-dichlorophenyl)-3-oxopropionitrile 
• 1023279-03-9 3-(2-benzyloxy-4-chlorophenyl)-5-(2,4-dichlorophenyl)-1H-pyrazole 
• 1023279-05-1 3-(2-benzyloxy-4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-decyl-1H-pyrazole 
• 1023279-06-2 5-(2-benzyloxy-4-chlorophenyl)-3-(2,4-dichlorophenyl)-1-decyl-1H-pyrazole 
• 1023279-08-4 5-(2-benzyloxy-4-chlorophenyl)-3-(2,4-dichlorophenyl)-1-dodecyl-1H-pyrazole 
• 1023279-07-3 3-(2-benzyloxy-4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-dodecyl-1H-pyrazole 
• 23288-92-8 2-mercapto-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole 
• 222056-36-2 5-(2,4-dichloro-phenyl)-2-(2,2-diethoxy-ethyl)-2H-pyrazol-3-ylamine 
• 26036-09-9 1-(2,4-dichlorobenzoyl)-3-thiosemicarbazide 

Relevant articles and documents

Synthesis, spectral analysis, antibacterial, antifungal, antioxidant and hemolytic activity studies of some new 2,5-disubstituted-1,3,4-oxadiazoles

Series of 1,3,4-oxadiazole derivatives (5a–5g and 5h, 5i) were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and HR-MS spectral analysis. All the target compounds were screened for their in vitro antibacterial activity against two Gram-negative bacterial strains namely Escherichia coli (MTCC 405) and Salmonella typhi (MTCC 3224) and two Gram-positive bacterial strains namely Bacillus subtilis (MTCC 1790) and Bacillus megaterium (MTCC 1684) and antifungal activity against Aspergillus niger (MTCC 282), Rhizopus oryzae (MTCC 262), Penicillium chrysogenum (MTCC 974), and Candida albicans (MTCC 183) fungal strains. The synthesized compounds exhibited significant antibacterial and antifungal potential. Three compounds (5e, 5f and 5g) have shown higher antibacterial activity with very low MIC values comparable to streptomycin. According to the SAR study, the antibacterial efficacy can be intensified by substituting fluoro and methyl substituents at the para position in acid hydrazide. The synthesized compounds were also screened for % radical scavenging activity by OH and DPPH assay and found to be good antioxidant agents. Besides, the hemolytic study revealed that the synthesized 1,3,4-oxadiazoles possessed negligible cytotoxicity compared with the standard.

Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests

To improve the insecticidal activity of (+)-nootkatone, a series of 42 (+)-nootkatone thioethers containing 1,3,4-oxadiazole/thiadiazole moieties were prepared to evaluate their insecticidal activities against Mythimna separata Walker, Myzus persicae Sulzer, and Plutella xylostella Linnaeus. Insecticidal evaluation revealed that most of the title derivatives exhibited more potent insecticidal activities than the precursor (+)-nootkatone after the introduction of 1,3,4-oxadiazole/thiadiazole on (+)-nootkatone. Among all of the (+)-nootkatone derivatives, compound 8c (1 mg/mL) exhibited the best growth inhibitory (GI) activity against M. separata with a final corrected mortality rate (CMR) of 71.4%, which was 1.54- and 1.43-fold that of (+)-nootkatone and toosendanin, respectively; 8c also displayed the most potent aphicidal activity against M. persicae with an LD50 value of 0.030 μg/larvae, which was closer to that of the commercial insecticidal etoxazole (0.026 μg/larvae); and 8s showed the best larvicidal activity against P. xylostella with an LC50 value of 0.27 mg/mL, which was 3.37-fold that of toosendanin and slightly higher than that of etoxazole (0.28 mg/mL). Furthermore, the control efficacy of 8s against P. xylostella in the pot experiments under greenhouse conditions was better than that of etoxazole. Structure-activity relationships (SARs) revealed that in most cases, the introduction of 1,3,4-oxadiazole/thiadiazole containing halophenyl groups at the C-13 position of (+)-nootkatone could obtain more active derivatives against M. separata, M. persicae, and P. xylostella than those containing other groups. In addition, toxicity assays indicated that these (+)-nootkatone derivatives had good selectivity to insects over nontarget organisms (normal mammalian NRK-52E cells and C. idella and N. denticulata fries) with relatively low toxicity. Therefore, the above results indicate that these (+)-nootkatone derivatives could be further explored as new lead compounds for the development of potential eco-friendly pesticides.

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.

Synthesis of novel indole derivatives containing double 1,3,4-oxadiazole moiety as efficient bactericides against phytopathogenic bacterium Xanthomonas oryzae

Abstract: A series of novel indole derivatives containing double 1,3,4-oxadiazole moiety was designed, synthesized and evaluated for their antibacterial activities in vitro. These compounds were fully characterized by 1H NMR, 13C NMR, and HRMS. Bioassay results indicated that most of title compounds exhibited excellent antibacterial activities against rice bacterial pathogen Xanthomonas oryzae (Xoo). For example, compounds 7d, 7h, 7i, 7j, 7k, 7l and 7m had the half-maximal effective concentration (EC50) values of 52.31, 54.12, 40.65, 38.80, 51.13, 52.75 and 50.66?μg/mL, respectively, which was better than that of commercial product bismerthiazol (BMT) (85.18?μg/mL). The experimental results proved that indole derivatives bearing double 1,3,4-oxadiazole unit are promising candidates for the development of new agricultural bactericides against pathogenic bacterium Xoo. Graphical abstract: [Figure not available: see fulltext.].

Design and synthesis of new norfloxacin-1,3,4-oxadiazole hybrids as antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA)

Toward the search of new antibacterial agents to control methicillin-resistant Staphylococcus aureus (MRSA), a class of new norfloxacin-1,3,4-oxadiazole hybrids were designed and synthesized. Antibacterial activities against drug-sensitive bacteria S. aureus and clinical drug resistant isolates of MRSA were evaluated. Compound 5k exhibited excellent antibacterial activities against S. aureus (MIC: 2 μg/mL) and MRSA1–3 (MIC: 0.25–1 μg/mL). The time-kill kinetics demonstrated that compound 5k had an advantage over commonly used antibiotics vancomycin in killing S. aureus and MRSA. Moreover, compound 5k could inhibit the bacteria and destroy their membranes in a short time, and showed very low cytotoxicity to NRK-52E cells. Some interesting structure-activity relationships (SARs) were also discussed. These results indicated that these norfloxacin-1,3,4-oxadiazole hybrids could be further developed into new antibacterial agents against MRSA.

Design, synthesis, insecticidal activity and 3D-QSR study for novel trifluoromethyl pyridine derivatives containing an 1,3,4-oxadiazole moiety

A series of trifluoromethyl pyridine derivatives containing 1,3,4-oxadiazole moiety was designed, synthesized and bio-assayed for their insecticidal activity. The result of bio-assays indicated the synthesized compounds exhibited good insecticidal activity against Mythimna separata and Plutella xylostella, most of the title compounds show 100% insecticidal activity at 500 mg L-1 and >80% activity at 250 mg L-1 against the two pests. Compounds E18 and E27 showed LC50 values of 38.5 and 30.8 mg L-1 against Mythimna separata, respectively, which were close to that of avermectin (29.6 mg L-1); compounds E5, E6, E9, E10, E15, E25, E26, and E27 showed 100% activity at 250 mg L-1, which were better than chlorpyrifos (87%). CoMFA and CoMSIA models with good predictability were proposed, which revealed the electron-withdrawing groups with an appropriate bulk at 2- and 4-positions of benzene ring could enhance insecticidal activity.

N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents

An electrophile, 2-bromo-N-(5-methyl-1,3-thiazol-2-yl)acetamide, was synthesized by the reaction of 5-methyl-1,3-thiazol-2-amine and bromoacetyl bromide in an aqueous medium. In a parallel scheme, a series of (un)substituted benzoic acids was converted sequentially into respective esters, acid hydrazides, and then into 1,3,4-oxadiazole heterocyclic cores. The electrophile was coupled with the aforementioned 1,3,4-oxadiazoles to obtain the targeted bi-heterocyles. Structural analysis of the synthesized compounds was performed by IR, EI-MS, 1H NMR, and 13C NMR. The enzyme inhibition study of these molecules was carried out against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, α-glucosidase, and urease. The interactions of these compounds with respective enzymes were recognized by their in silico study. Moreover, their cytotoxicity was also determined to find out their utility as possible therapeutic agents.

Solvent- and Metal-free Oxidative Esterification of Aromatic Aldehydes Using Urea-2,2-dihydroperoxypropane as a New Solid Oxidant

Urea-2,2-dihydroperoxypropane as a noble and solid gem-dihydroperoxide derivative was used to transform various aromatic aldehydes to their corresponding benzoate derivatives in the presence of HBr under mild conditions at room temperature in high yields and short reaction times.

Inhibitory growth evaluation and apoptosis induction in MCF-7 cancer cells by new 5-aryl-2-butylthio-1,3,4-oxadiazole derivatives

Background: Cancer has become one of the global health issues and it is the life-threatening disease characterized by unrestrained growth of cells. Despite various advances being adopted by chemotherapeutic management, the use of the current anticancer drugs such as Doxorubicin, Asparginase, Methotrexate, Vincristine remains limited due to high toxicity, side effects and developing drug resistance. Apoptosis is a crucial cellular process and improper regulation of apoptotic signaling pathways may lead to cancer formation. Subsequently, the synthesis of effective chemotherapeutic agents that can induce apoptosis in tumor cell has emerged as a significant approach in cancer drug discovery. Methods: The goal of this work is to develop a potential antitumor agent exerting significant inhibitory effects on cancer cell and low cytotoxicity, for which we focused on the structural features of 1,3,4-oxadiazoles as it a privileged scaffold in modern medicinal chemistry and have the ability to inhibit growth factors, enzymes and kinases potentially involved in the attainment of cellular immortality and carcinogenesis. Result: In vitro MTT screening assay showed the compound 5-aminophenyl-2-butylthio-1,3,4-oxadiazole (5e) showing the highest inhibitory effect against MCF-7 cancer cell with IC50 value 10.05?±?1.08?μM while it is much safer and less toxic on normal cell line (HEK-293). The dose-dependent treatment of MCF-7 cells with 5e resulted in inhibition of cell migration in the wound healing assay. The flow-cytometry analysis showed the cells arrested in G0/G1 phase of the cell cycle. Compound 5e induced apoptosis of MCF-7 cells was characterized using DAPI staining and Annexin V-PE/7-AAD dual binding assay. Reduction of NBT by compound 5e showed a reduced generation of ROS. Western blotting studies showed high activation of apoptotic protein Caspase3 and decrease in expression of anti-apoptotic protein BCL-2. Conclusion: Based on the results of in vitro studies, it could be concluded that compound 5e showed a significant inhibitory growth effect on MCF-7 cells and have the potential to be developed as lead molecule and further structural modifications may result in promising new anticancer agents.

Synthesis and Biological Activity of Anthranilic Diamide Derivatives Incorporating 1,3,4-oxadiazole or Nitrogen-containing Saturated Heterocyclic Moieties

A series of novel anthranilic diamide derivatives incorporating 1,3,4-oxadiazole or nitrogen-containing saturated heterocyclic moieties were synthesized, characterized, and evaluated for bacteriostatic activity against three phytopathogenic bacteria Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (R. solanacearum). The preliminary biological results indicated that most compounds exhibit bacteriostatic activity against three phytopathogenic bacteria. Among these compounds, compounds 6g, 6f, and 6i displayed better antibacterial activity. In the test with concentration of 200 μg/mL, antibacterial activity of compound 6i and 6j was 96%. In particular, the bacteriostatic activity displayed by compound 6h against Xoo is similar to the one displayed by commercial drug bismerthiazol.