568544-04-7

Basic information

• Product Name: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE
• Synonyms: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE
• CAS NO: 568544-04-7
• Molecular Formula: C₉H₆BrClN₂O
• Molecular Weight: 273.51
• Mol File: 568544-04-7.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE(568544-04-7)
• EPA Substance Registry System: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE(568544-04-7)

Safety Data

• Hazardous Substances Data: 568544-04-7(Hazardous Substances Data)

Usage

General Description

2-(4-Bromo-phenyl)-5-chloromethyl-[1,3,4]oxadiazole, also known as BPOX, is a chemical compound with a molecular formula C9H6BrClN2O. It is a heterocyclic compound containing an oxadiazole ring, as well as bromine and chlorine substituents. BPOX has shown potential as a building block in the synthesis of pharmaceutical compounds and agrochemicals, due to its diverse reactivity and ability to participate in various chemical reactions. It also exhibits interesting biological activities, including anti-inflammatory and antitumor properties, which make it a promising candidate for drug development. BPOX is mainly used in research and development in the pharmaceutical and agrochemical industries.

Upstream product

• 5798-75-4 Ethyl 4-bromobenzoate 
• 79-11-8 chloroacetic acid 
• 5933-32-4 4-bromobenzoic acid hydrazide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 199938-23-3 4-bromo-N’-(chloroacetyl)benzohydrazide 

Downstream Products

• 871583-95-8 2-benzylaminomethyl-5-(4-bromophenyl)-1,3,4-oxadiazole 
• 911061-99-9 2-(4-bromophenyl)-5-(1H-pyrazol-1-ylmethyl)-1,3,4-oxadiazole 
• 911061-96-6 2-(4-bromophenyl)-5-(methoxymethyl)-1,3,4-oxadiazole 
• 871583-96-9 benzyl{[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]methyl}[(6-methoxy-3-nitropyridin-2-yl)methyl]amine 
• 1250479-78-7 2-(azidomethyl)-5-(4-bromophenyl)-1,3,4-oxadiazole 
• 1279822-43-3 tert-butyl N-[[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]methyl]carbamate 
• 1453855-93-0 1-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]-N,N-dimethylmethanamine 
• 911062-10-7 3-(4-bromophenyl)-4-(4-methoxyphenyl)-5-(1H-pyrazol-1-ylmethyl)-4H-1,2,4-triazole 
• 911062-06-1 5-[3-(4-bromophenyl)-5-(methoxymethyl)-4H-1,2,4-triazol-4-yl]-2-methoxypyridine 
• 871583-86-7 1-(4-bromophenyl)-8-methoxy-4H,6H-[1,2,4]triazolo[4,3-a][4,1]benzoxazepine 

Relevant articles and documents

Synthesis and biological evaluation of honokiol derivatives bearing 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3h)-ones as potential viral entry inhibitors against sars-cov-2

The 2019 coronavirus disease (COVID-19) caused by SARS-CoV-2 virus infection has posed a serious danger to global health and the economy. However, SARS-CoV-2 medications that are specific and effective are still being developed. Honokiol is a bioactive component from Magnoliae officinalis Cortex with damp-drying effect. To develop new potent antiviral molecules, a series of novel honokiol analogues were synthesized by introducing various 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3H)-ones to its molecule. In a SARS-CoV-2 pseudovirus model, all honokiol derivatives were examined for their antiviral entry activities. As a result, 6a and 6p demonstrated antiviral entry effect with IC50 values of 29.23 and 9.82 μM, respectively. However, the parental honokiol had a very weak antiviral activity with an IC50 value more than 50 μM. A biolayer interfero-metry (BLI) binding assay and molecular docking study revealed that 6p binds to human ACE2 protein with higher binding affinity and lower binding energy than the parental honokiol. A competitive ELISA assay confirmed the inhibitory effect of 6p on SARS-CoV-2 spike RBD’s binding with ACE2. Importantly, 6a and 6p (TC50 > 100 μM) also had higher biological safety for host cells than honokiol (TC50 of 48.23 μM). This research may contribute to the discovery of potential viral entrance inhibitors for the SARS-CoV-2 virus, although 6p’s antiviral efficacy needs to be validated on SARS-CoV-2 viral strains in a biosafety level 3 facility.

One-potCuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4/1,2,4-oxadiazoles starting from available chloromethyl-1,3,4/1,2,4-oxadiazoles

The one-pot CuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4-oxadiazole and (1H-1,2,3-triazol-1-yl)methyl-1,2,4-oxadiazole derivatives via three-component reaction of consequent nucleophilic substitution of chlorine, with azide, and its further “cli

Design, synthesis, evaluation, and molecular docking of ursolic acid derivatives containing a nitrogen heterocycle as anti-inflammatory agents

Ursolic acid derivatives containing oxadiazole, triazolone, and piperazine moieties were synthesized in an attempt to develop potent anti-inflammatory agents. Structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, and HRMS. Most of the synthesized compounds showed pronounced anti-inflammatory effects at 100 mg/kg. In particular, compound 11b, which displayed the most potent anti-inflammatory activity of all of the compounds prepared, with 69.76% inhibition after intraperitoneal administration, was more potent than the reference drugs indomethacin and ibuprofen. The cytotoxicity of the compounds was also assessed by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay, and no compounds showed any appreciable cytotoxic activity (IC50 >100 μmol/L). Furthermore, molecular docking studies of the synthesized compounds were performed to rationalize the obtained biological results. Overall, the results indicate that compound 11b could be a therapeutic candidate for the treatment of inflammation.