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
• Article Data: 7

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

General Description

Ethyl 2-chloro-5-nitrobenzoate is a chemical compound with the molecular formula C9H8ClNO4. It is a yellow crystalline solid that is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Ethyl 2-chloro-5-nitrobenzoate is known for its nitroaromatic properties, which make it useful in the production of dyes and pigments. It is also used in the manufacture of other organic compounds, including intermediates for a variety of organic synthesis processes. Ethyl 2-chloro-5-nitrobenzoate is considered to be a hazardous substance and should be handled and used with proper safety precautions.

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.

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.

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

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