15500-74-0

Basic information

• Product Name: Benzonitrile,4-chloro-N-oxide
• Synonyms: Benzonitrile,4-chloro-N-oxide
• CAS NO: 15500-74-0
• Molecular Formula: C₇H₄ClNO
• Molecular Weight: 153.56576
• Mol File: 15500-74-0.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.2g/cm³
• Refractive Index: 1.55
• CAS DataBase Reference: Benzonitrile,4-chloro-N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile,4-chloro-N-oxide(15500-74-0)
• EPA Substance Registry System: Benzonitrile,4-chloro-N-oxide(15500-74-0)

Safety Data

• Hazardous Substances Data: 15500-74-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H4ClNO/c8-7-3-1-6(2-4-7)5-9-10/h1-4H

Upstream product

• 133362-01-3 4-chloro-α-nitro-benzaldehyde seqtrans-oxime 
• 3848-36-0 4-chlorobenzaldoxime 
• 74903-80-3 (Z)-N-hydroxy-4-chloro-benzenecarboximidoyl chloride 
• 104-88-1 4-chlorobenzaldehyde 
• 3717-24-6 4-chlorobenzaldehyde oxime 
• 29559-24-8 4-chlorophenylnitromethane 
• 33341-64-9 N-Chloro-4-chlorobenzamide 

Downstream Products

• 10284-99-8 1-[3-(4-chlorophenyl)-isoxazol-5-yl]piperidine 
• 5301-02-0 5-(chloromethyl)-3-(4-chlorophenyl)isoxazole 
• 10285-02-6 1-[3-(4-chlorophenyl)-isoxazol-5-yl]morpholine 
• 21614-47-1 3-(4-chlorophenyl)-5-methyl-1,2,4-oxadiazole 
• 21614-50-6 3-(4-chloro-phenyl)-5-phenethyl-[1,2,4]oxadiazole 
• 21614-48-2 3-(4-chloro-phenyl)-5-(2-ethoxy-ethyl)-[1,2,4]oxadiazole 
• 71637-71-3 3-(4-chloro-phenyl)-3a,5-diethyl-6,6a-diphenyl-(3ar,6ac)-3a,6a-dihydro-cyclopenta[d]isoxazol-4-one 
• 71637-79-1 3-(4-chloro-phenyl)-3a-ethyl-5,6,6a-triphenyl-(3ar,6ac)-3a,6a-dihydro-cyclopenta[d]isoxazol-4-one 
• 10284-98-7 1-[3-(4-chlorophenyl)-isoxazol-5-yl]-4-methylpiperazine 
• 29363-96-0 5-butyl-3-(4-chlorophenyl)isoxazole 
• 66168-72-7 3-(4-chloro-phenyl)-3a,5,6,6a-tetraphenyl-(3ar,6ac)-3a,6a-dihydro-cyclopenta[d]isoxazol-4-one 
• 13273-57-9 3-(4-chlorophenyl)-5-phenyl-1,2,4-oxadiazole 
• 21614-49-3 5-benzyl-3-(4-chloro-phenyl)-[1,2,4]oxadiazole 
• 29363-97-1 ethyl 3-(4′-chlorophenyl)isoxazole-5-carboxylate 

Relevant articles and documents

Regioselective Synthesis of Fluorosulfonyl 1,2,3-Triazoles from Bromovinylsulfonyl Fluoride

A regioselective metal-free preparation of 4-fluorosulfonyl 1,2,3-triazoles from organic azides and a hitherto underexplored bromovinylsulfonyl fluoride building block is described. This reaction is very general and was extended to the synthesis of variou

Control of regioselectivity in nitrile oxide cycloadditions to cinnamic acid derivatives

Tertiary cinnamides undergo cycloaddition with benzonitrile oxides producing the 5-phenyl and 4-phenyl regioisomers 2b and 3b in a 25-30:75-70 ratio. This result is opposite to that obtained utilizing methyl cinnamate 1a as the dipolarophile. A synthetically useful method for the preparation of the acid 3c, derived from what is usually the minor regioisomer, has been developed by taking advantage of this reversal of regiochemistry.

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 Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies

Abstract: Regioselective synthesis of some novel 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one linked isoxazole hybrids via copper(I) catalyzed one-pot reaction of various aromatic aldehydes with 7-bromo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one was developed. The structures of the compounds that are synthesized are confirmed by 1H NMR, 13C NMR, and mass spectra. All the hybrids have been tested for their in vitro anticancer activity against four human cancer cell lines, including HeLa, MCF-7, A549, and PC3. Three of the compounds exhibited remarkable anticancer activity compared to standard drug etoposide. Molecular docking studies with EGFR also strengthened the in vitro anticancer activity.

One-pot Synthesis of Some Novel Xanthine Derived Isoxazoles as Potent Antibacterial Agents

In search of better antibacterial agents, a series of novel xanthine derived 3,5-disubstituted isoxazole derivatives were synthesized (3a-3j) in one-pot using 8-chloro-1,3-dimethyl-7-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione and aromatic aldehydes and f

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

Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles

Reductive ring transformation of 3-substituted 5-(2-nitrophenyl)isoxazoles, readily accessible via 1,3-dipolar cycloaddition of 2-ethinylnitrobenzene with nitrile oxides, opens a novel access to 2-substituted quinolin-4-ones. Nickel boride, generated in situ from nickel chloride and sodium borohydride, allows, via simultaneous reduction of the nitro group and reductive cleavage of the isoxazole ring, the one-step conversion into the target quinolin-4-ones. This protocol tolerates various functional groups, except olefins, and thus is complementary to the reductive ring transformation with iron/acetic acid, which predominantly tolerates olefins.

Synthesis, antimalarial activity, and target binding of dibenzazepine-tethered isoxazolines

Malaria, a complex and deadly parasitic infectious disease, is a huge public health problem in many endemic countries around the globe. The prevailing extensive resistance of malaria parasites to traditional drugs and emergence of resistance to the currently used frontline artemisinin-based chemotherapy calls for the development of new drugs. Towards this objective and since compounds containing the dibenzazepine moiety are effective in treating both gametocyte and asexual stage malaria parasites, including multi drug resistant parasites, a library of dibenzazepine tethered 3,5-disubstituted isoxazolines was synthesised via 1,3-dipolar cycloaddition reaction. An additional diversified group of dibenzazepine derivatives were accessed by Suzuki coupling of one of the above dibenzazepine derivatives with various organoboronic acids. All compounds were structurally characterized and were evaluated for their antimalarial activity. They exhibited good to excellent inhibitory activity against the growth of drug-sensitive Plasmodium falciparum 3D7 strain with IC50 values ranging from 0.2 to 7.7 μM. About 50% of the compounds were either minimally or not toxic to human cell lines. Five of the compounds (6j, 6k, 8c, 8k and 8l) that highly inhibited the parasite growth were further assessed for antimalarial activity using an additional chloroquine-sensitive (D6) and two chloroquine-resistant (W2 and 7G8) P. falciparum strains. These compounds were effective against all four strains (3D7, D6, W2 and 7G8), exhibiting IC50 values of 0.1 to 1.75 μM. The dibenzazepines were identified to target the metalloamino-peptidase of parasites. Molecular docking and dynamics simulation studies were performed to understand the binding mode and binding strengths of the selected compounds with the enzyme. In agreement with their excellent antimalarial activity, the data suggested that the compounds can strongly bind to the active site of the enzyme.

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.