16588-17-3

Basic information

• Product Name: Ethyl 2-chloro-5-nitrobenzoate
• Synonyms: RARECHEM AL BI 0191;ETHYL 2-CHLORO-5-NITROBENZOATE;BENZOIC ACID, 2-CHLORO-5-NITRO-, ETHYL ESTER;2-Chloro-5-nitrobenzoicacidethylester
• CAS NO: 16588-17-3
• Molecular Formula: C₉H₈ClNO₄
• Molecular Weight: 229.62
• Product Categories: Esters;Phenyls & Phenyl-Het
• Mol File: 16588-17-3.mol

Chemical Properties

• Boiling Point: 329.5 °C at 760 mmHg
• Flash Point: 153.1 °C
• Appearance: /
• Density: 1.369 g/cm³
• Vapor Pressure: 0.000177mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: Ethyl 2-chloro-5-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-chloro-5-nitrobenzoate(16588-17-3)
• EPA Substance Registry System: Ethyl 2-chloro-5-nitrobenzoate(16588-17-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 16588-17-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Ethyl 2-chloro-5-nitrobenzoate is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical structure allows it to be a valuable component in the development of new drugs and agricultural products, enhancing their efficacy and performance.
Used in Dye and Pigment Production:
Leveraging its nitroaromatic properties, Ethyl 2-chloro-5-nitrobenzoate is utilized in the production of dyes and pigments. Its ability to impart color and stability makes it a preferred choice in the formulation of various colorants used across different industries.
Used in Organic Synthesis:
Ethyl 2-chloro-5-nitrobenzoate serves as an intermediate in a variety of organic synthesis processes. Its versatility in chemical reactions enables the creation of a wide range of organic compounds, contributing to the advancement of chemical research and development.
Safety Precautions:
Given its classification as a hazardous substance, Ethyl 2-chloro-5-nitrobenzoate requires careful handling and use. Proper safety measures should be implemented to minimize risks associated with its use, ensuring the well-being of individuals and the environment.

InChI:InChI=1/C9H8ClNO4/c1-2-15-9(12)7-5-6(11(13)14)3-4-8(7)10/h3-5H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 
• 96-97-9 5-nitrosalicylic acid 

Downstream Products

• 80568-07-6 ethyl 2-<(5-chloro-2-methylphenyl)thio>-5-nitrobenzoate 
• 61346-19-8 5-nitroindazolin-3-one 
• 861782-39-0 2-hydrazino-5-nitro-benzoic acid ethyl ester 
• 861360-67-0 5-nitro-2-phenyl-1,2-dihydro-3H-indazol-3-one 
• 861782-16-3 ethyl 5-nitro-2-(2-phenylhydrazino)benzoate 
• 119342-74-4 (amino-2 ethylthio)-2 nitro-5 benzoate d'ethyle 
• 64401-55-4 5-amino-2-chloro-benzoic acid ethyl ester 
• 83909-57-3 2-Cyclohexylamino-5-nitro-benzoic acid ethyl ester 
• 119342-77-7 (orthoaminophenylthio)-2 nitro-5 benzoate d'ethyle 
• 65192-78-1 nitro-2 dibenzothiazepin-1,4 one-11 
• 83909-37-9 5-Amino-2-cyclohexylamino-benzoic acid ethyl ester; hydrochloride 
• 80568-10-1 2-(5-chloro-2-methyl-phenylsulfanyl)-5-nitro-benzoic acid 
• 80568-08-7 7-amino-1-<<2-(diethylamino)ethyl>amino>-4-methylthioxanthenone 
• 794523-83-4 5-amino-2-sulfanilyl-benzoic acid ethyl ester 

Relevant articles and documents

Design, synthesis, and anti-proliferative evaluation of new quinazolin-4(3H)-ones as potential VEGFR-2 inhibitors

Inhibiting VEGFR-2 has been set up as a therapeutic strategy for treatment of cancer. Thus, nineteen new quinazoline-4(3H)-one derivatives were designed and synthesized. Preliminary cytotoxicity studies of the synthesized compounds were evaluated against three human cancer cell lines (HepG-2, MCF-7 and HCT-116) using MTT assay method. Doxorubicin and sorafenib were used as positive controls. Five compounds were found to have promising cytotoxic activities against all cell lines. Compound 16f, containing a 2-chloro-5-nitrophenyl group, has emerged as the most active member. It was approximately 4.39-, 5.73- and 1.96-fold more active than doxorubicin and 3.88-, 5.59- and 1.84-fold more active than sorafenib against HepG2, HCT-116 and MCF-7 cells, respectively. The most active cytotoxic agents were further evaluated in vitro for their VEGFR-2 inhibitory activities. The results of in vitro VEGFR-2 inhibition were consistent with that of the cytotoxicity data. Molecular docking of these compounds into the kinase domain, moreover, supported the results.

New quinoxaline-2(1H)-ones as potential VEGFR-2 inhibitors: design, synthesis, molecular docking, ADMET profile and anti-proliferative evaluations

Eleven new quinoxaline derivatives were designed and synthesized as modified VEGFR-2 inhibitors of our previous work. The synthesized compounds were tested against three human cancer cell lines (HepG-2, MCF-7 and HCT-116). Compounds11g,11eand11cwere the most potent members against the tested cells. Compound11g(IC50= 4.50, 2.40, and 5.90 μM) was the most potent member compared to doxorubicin (IC50= 8.29, 9.65, and 7.68 μM) and sorafenib (IC50= 7.33, 9.41, and 7.23 μM) against HepG-2 and HCT-116, and MCF-7 cell lines, respectively. Compound11eshowed better anti-proliferative activities than doxorubicin and sorafenib with IC50values of 5.34, 4.19, and 6.06 μM, against HepG-2 and HCT-116 and MCF-7 cell lines, respectively. In addition, the most active anti-proliferative derivatives11c,11e,11f, and11gwere selected to evaluate their inhibitory activities against VEGFR-2. The tested compounds displayed good inhibitory activity with IC50values ranging from 0.75 to 1.36 μM. Among them, compound11gwas the most active member with an IC50value of 0.75 μM, compared to the reference drug; sorafenib (IC50= 1.29 μM). Moreover, docking studies revealed that the synthesized compounds have good binding patterns against the prospective molecular target; VEGFR-2. In addition,in silico, ADMET and toxicity studies showed a high level of drug likeness for the synthesized compounds.

Discovery of new quinazolin-4(3H)-ones as VEGFR-2 inhibitors: Design, synthesis, and anti-proliferative evaluation

Sixteen novel quinazoline-based derivatives were designed and synthesized via modification of the VEGFR-2 reported inhibitor 7 in order to increase the binding affinity of the designed compounds to the receptor active site. The designed compounds were evaluated for their VEGFR-2 inhibitory effects. Inhibiting VEGFR-2 has been set up as a therapeutic strategy for treatment of cancer. The bioactivity of the new compounds was performed against HepG-2, MCF-7 and HCT-116 cell lines. Doxorubicin and sorafenib were used as positive controls. Compound 18d was observed to have promising cytotoxic activity (IC50 = 3.74 ± 0.14, 5.00 ± 0.20 and 6.77 ± 0.27 μM) in comparison to the reference drug doxorubicin (IC50 = 8.28, 9.63 and 7.67 μM) and sorafenib (IC50 = 7.31, 9.40 and 7.21 μM). The most active compounds were tested for their in vitro VEGFR-2 inhibitory activities. Results of VEGFR-2 inhibition were consistent with that of the cytotoxicity data. Thus, compound 18d showed VEGFR-2 inhibitory activity (IC50 = 0.340 ± 0.04 μM) superior to that of the reference drug, sorafenib (IC50 = 0.588 ± 0.06 μM). Furthermore, docking study was performed in order to understand the binding pattern of the new compounds into VEGFR-2 active site. Docking results attributed the potent VEGFR-2 inhibitory effect of the new compounds as they bound to the key amino acids in the active site, Glu883 and Asp1044, as well as their hydrophobic interaction with the receptor hydrophobic pocket. Results of cytotoxic activities, in vitro VEGFR-2 inhibition together with docking study argument the advantages of the synthesized analogues as promising anti-angiogenic agents.

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.

NOVEL 4,6-DISUBSTITUTED AMINOPYRIMIDINE DERIVATIVES HAVING BOTH AROMATIC AND HALOGENIC SUBSTITUENTS

Certain 4,6-disubstituted aminopyrimidine derivatives having both aromatic and halogenic substituents.

Synthesis and antitubercular activities of substituted benzoic acid N′-(substituted benzylidene/furan-2-ylmethylene)-N-(pyridine-3-carbonyl)- hydrazides

A series of benzoic acid hydrazones and its nicotinyl derivatives (1-10) were prepared and evaluated for their antitubercular activity towards a strain of Mycobacterium tuberculosis (MTB). The structures of newly synthesized compounds were confirmed by infrared (IR) and 1H-nuclear magnetic resonance (NMR) spectral data and elemental analysis. The in vitro antitubercular activity of synthesized compounds against MTB was carried out in Middlebrook 7H11agar medium supplemented with OADC by agar dilution method. The antitubercular activity results indicated that nicotinic acid N-(3,5-dinitro-benzoyl)-N′-(4-methoxy-benzylidene)-hydrazide (1) is the most potent among the synthesized compounds with MIC of 3.5 × 10 -3 μM.

PPAR-γ modulators

Modulators of PPARγ activity are provided which are useful in pharmaceutical compositions and methods for the treatment of conditions such as type II diabetes and obesity.