13820-15-0

Basic information

• Product Name: Benzonitrile, 3-chloro-, N-oxide
• CAS NO: 13820-15-0
• Molecular Formula: C7H4ClNO
• Molecular Weight: 153.568
• Mol File: 13820-15-0.mol

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 3-chloro-, N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 3-chloro-, N-oxide(13820-15-0)
• EPA Substance Registry System: Benzonitrile, 3-chloro-, N-oxide(13820-15-0)

Safety Data

• Hazardous Substances Data: 13820-15-0(Hazardous Substances Data)

Upstream product

• 29203-59-6 3-chloro-N-hydroxybenzimidoyl chloride 
• 34158-71-9 3-chlorobenzaldehyde oxime 
• 587-04-2 m-Chlorobenzaldehyde 
• 33341-68-3 N-Chloro-m-chlor-benzamid 

Downstream Products

• 103566-02-5 5-ethynyl-3-(3-chloro-phenyl)-isoxazole 
• 107524-50-5 3,3'-bis-(3-chloro-phenyl)-[5,5']biisoxazolyl 
• 107523-14-8 3-(3-chloro-phenyl)-3'-phenyl-[5,5']biisoxazolyl 
• 105947-13-5 1-[3-(3-chloro-phenyl)-isoxazol-5-yl]-butan-1-one 
• 89047-03-0 3-(3-Chloro-phenyl)-5-nitro-4,5-dihydro-isoxazole 
• 26218-71-3 3,4-Bis(3-chlorophenyl)furoxan 
• 89047-06-3 3-(3-chlorophenyl)isoxazole 
• 1424394-75-1 C₁₂H₁₂ClNO₃ 
• 1171190-67-2 3-(3-chlorophenyl)-5-methyl-4-phenylisoxazole 
• 107519-50-6 3-(3-chloro-phenyl)-isoxazole-5-carboxylic acid anilide 
• 100517-43-9 3-(3-chlorophenyl)-1,2-oxazole-5-carboxylic acid 

Relevant articles and documents

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

One Pot Synthesis and Antitumor Activity of Isoxazole-Pyrimido[4,5-c]isoquinolines

Abstract: A number of new isoxazole coupled pyrimido[4,5-c]isoquinolines has been synthesized in good to excellent yields by the one pot method. The Cu(I)-catalyzed cycloaddition reaction between the terminal alkyne 4 and various aldehydes has led to nitr

Cu(I)-Catalysis of One-Pot Synthesis of Some Novel Regioselective Isoxazole-Benzimidazole Hybrids and Their In Vitro Anti-Cancer Evaluation

Regioselective synthesis of some novel isoxazole-benzimidazole hybrids in high yields via Cu(I)-catalyzed tandem one-pot reaction of aromatic aldehydes with 1-prop-2-ynylbenzimidazole is developed. Structures of the synthesized compounds are confirmed by

Design, synthesis, and evaluation of hydroxamic acid derivatives as promising agents for the management of Chagas disease

Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5-dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g) was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to 1 μM). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.

Synthesis, pharmacological characterization, and docking analysis of a novel family of diarylisoxazoles as highly selective cyclooxygenase-1 (COX-1) inhibitors

3-(5-Chlorofuran-2-yl)-5-methyl-4-phenylisoxazole (P6), a known selective cyclooxygenase-1 (COX-1) inhibitor, was used to design a new series of 3,4-diarylisoxazoles in order to improve its biochemical COX-1 selectivity and antiplatelet efficacy. Structure-activity relationships were studied using human whole blood assays for COX-1 and COX-2 inhibition in vitro, and results showed that the simultaneous presence of 5-methyl (or -CF3), 4-phenyl, and 5-chloro(-bromo or -methyl)furan-2-yl groups on the isoxazole core was essential for their selectivity toward COX-1. 3g, 3s, 3d were potent and selective COX-1 inhibitors that affected platelet aggregation in vitro through the inhibition of COX-1-dependent thromboxane (TX) A2. Moreover, we characterized their kinetics of COX-1 inhibition. 3g, 3s, and 3d were more potent inhibitors of platelet COX-1 and aggregation than P6 (named 6) for their tighter binding to the enzyme. The pharmacological results were supported by docking simulations. The oral administration of 3d to mice translated into preferential inhibition of platelet-derived TXA2 over protective vascular-derived prostacyclin (PGI2).

One-Pot Synthesis of 3-Substituted Isoxazoles from Phenyl Vinylic Selenide

Phenyl vinylic selenide was adopted for 1,3-dipolar cycloaddition to nitrile oxides and subsequent oxidation-elimination furnished 3-substituted isoxazoles with good yields in a one-pot, two-step transformation.

The 1,3-dipolar cycloadditions of nitrile oxides and nitrile imines to alkyl dicyanoacetates

The readily available alkyl dicyanoacetates 1 reacted with the 1,3-dipolar reagents arenecarbonitrile oxides 2′ and arenecarbonitrile imines 5′ to afford 1,2,4-oxadiazol and 1,2,4-triazol derivatives. The arenecarbonitrile oxides 2′ with electron-donating

SYNTHESIS OF 3-ARYL-4,5-DIHYDRO-5-HYDROXY-1,2-OXAZOLES BY REACTION OF SUBSTITUTED BENZONITRILE OXIDES WITH THE ENOLATE ION OF ACETALDEHYDE.

By reaction of substituted benzonitrile oxides with the enolate ion of acetaldehyde (quantitatively generated by the known cycloreversion of THF in the presence of n-butyllithium) a number of 3-aryl-4,5-dihydro-5-hydroxy-1,2-oxazoles (previously unknown or, in two cases, only synthesized by different procedures) have been isolated in high yields.Treatment of such hydroxy-isoxalines with some common bases allows their conversion in high yields into the corresponding isoxazoles.

SYNTHESIS AND PROPERTIES OF AZOLS AND THEIR DERIVATIVES. PART VI. CYCLOADDITION REACTIONS OF NITROETHYLENE WITH AROMATIC NITRILE N-OXIDES AND SOME CONVERSIONS OF 3-ARYL-5-NITRO-4,5-DIHYDRO-1,2-OXAZOLES

Reactions of aromatic nitrile N-oxides with nitroethylene lead to formation of 3-aryl-5-nitro-4,5-dihydro-1,2-oxazoles.During heating the above compounds decompose with elimination of nitrous acid, thus affording 3-aryl-1,2-oxazoles.Under nucleophilic reagents a ring opening was observed.