1822-94-2

Basic information

• Product Name: 5-(CHLOROMETHYL)-3-PHENYL-1,2,4-OXADIAZOLE
• Synonyms: AKOS BB-7023;5-(CHLOROMETHYL)-3-PHENYL-1,2,4-OXADIAZOLE;CHEMBRDG-BB 4017587;5-Chloromethyl-3-(4-fluoro-phenyl)-;5-(chloromethyl)-3-phenyl-1,2,4-oxadiazole(SALTDATA: FREE);1,2,4-Oxadiazole, 5-(chloromethyl)-3-phenyl-;3-Phenyl-5-chloromethyl-1,2,4-oxadiazole
• CAS NO: 1822-94-2
• Molecular Formula: C₉H₇ClN₂O
• Molecular Weight: 194.62
• Mol File: 1822-94-2.mol

Chemical Properties

• Melting Point: 42 °C
• Boiling Point: 142 °C
• Flash Point: 145.5°C
• Appearance: /
• Density: 1.283
• Vapor Pressure: 0.00103mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: 2-8°C
• PKA: -2?+-.0.32(Predicted)
• CAS DataBase Reference: 5-(CHLOROMETHYL)-3-PHENYL-1,2,4-OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(CHLOROMETHYL)-3-PHENYL-1,2,4-OXADIAZOLE(1822-94-2)
• EPA Substance Registry System: 5-(CHLOROMETHYL)-3-PHENYL-1,2,4-OXADIAZOLE(1822-94-2)

Safety Data

• Hazard Codes: C,Xn
• Statements: 22
• Hazardous Substances Data: 1822-94-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(Chloromethyl)-3-phenyl-1,2,4-oxadiazole is used as a building block for the synthesis of pharmaceutical compounds due to its unique chemical structure and potential biological activities, such as antibacterial and antifungal properties. Its versatility allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical industry, 5-(Chloromethyl)-3-phenyl-1,2,4-oxadiazole is utilized as a key intermediate in the synthesis of agrochemicals with pesticidal properties. Its incorporation into these compounds can enhance their effectiveness in controlling pests and diseases in agriculture, thereby improving crop yields and food security.
Used in Material Science:
5-(Chloromethyl)-3-phenyl-1,2,4-oxadiazole also finds applications in material science, where it can be used to develop new materials with specific properties. Its unique structure allows for the creation of materials with improved thermal stability, chemical resistance, and other desirable characteristics for various industrial applications.
Overall, 5-(Chloromethyl)-3-phenyl-1,2,4-oxadiazole is a versatile chemical compound with a wide range of potential applications in the pharmaceutical, agrochemical, and material science industries. Its unique structure and properties make it a valuable building block for the development of innovative products and solutions.

InChI:InChI=1/C9H6ClFN2O/c10-5-8-12-9(13-14-8)6-1-3-7(11)4-2-6/h1-4H,5H2

Upstream product

• 873-67-6 benzonitrile oxide 
• 107-14-2 chloroacetonitrile 
• 21251-95-6 N-chloroacetoxy-benzamidine 
• 79-04-9 chloroacetyl chloride 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 2549-51-1 vinyl chloroacetate 
• 21251-95-6 (Z)-N'-(2-chloroacetoxy)benzimidamide 
• 613-92-3 N-hydroxyl-benzamidine 
• 22118-09-8 2-bromoacetyl chloride 
• 613-92-3 N-hydroxybenzamidine 
• 100-47-0 benzonitrile 
• 613-92-3 (E)-N'-hydroxybenzimidamide 
• 1401223-69-5 C₉H₉ClN₂O₂ 

Downstream Products

• 91959-17-0 3-phenyl-5-pyrrolidin-1-ylmethyl-[1,2,4]oxadiazole 
• 73217-38-6 1-(3-phenyl-[1,2,4]oxadiazol-5-ylmethyl)-pyridinium; chloride 
• 93475-45-7 isobutyl-(3-phenyl-[1,2,4]oxadiazol-5-ylmethyl)-amine 
• 4915-88-2 3-phenyl-5-((phenylthio)methyl)-1,2,4-oxadiazole 
• 125983-58-6 Morpholin-4-yl-(3-phenyl-[1,2,4]oxadiazol-5-yl)-methanethione 
• 1195982-96-7 (R)-3-(1-phenylcycloheptanecarbonyloxy)-1-(3-phenyl[1,2,4]oxadiazol-5-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 90886-85-4 C-[3-(3-nitro-phenyl)-[1,2,4]oxadiazol-5-yl]-methylamine 
• 110722-43-5 [4-Oxo-3-(3-phenyl-[1,2,4]oxadiazol-5-ylmethyl)-3,4-dihydro-phthalazin-1-yl]-acetic acid 

Relevant articles and documents

In vitro anti-TB properties, in silico target validation, molecular docking and dynamics studies of substituted 1,2,4-oxadiazole analogues against Mycobacterium tuberculosis

The alarming increase in multi- and extensively drug-resistant (MDR and XDR) strains of Mycobacterium tuberculosis (MTB) has triggered the scientific community to search for novel, effective, and safer therapeutics. To this end, a series of 3,5-disubstitu

2,3-diketone indole compound, preparation method and applications thereof

The invention discloses a 2,3-diketone indole compound, a preparation method and applications thereof, wherein the compound has a structure represented by the following general formula (I) or (II). The invention further relates to a pharmaceutical composi

Synthesis of Some Azamacrocycles Bearing 1,2,4-Oxadiazole and 1,2,3-Triazole Moieties

Abstract: A tetraazacrown ether,4,9-di(prop-2-yn-1-yl)-1,4,9,12-tetraazacyclohexadecane-2,11-dione, bearingpropargyl groups on two nitrogens was synthesized starting from1,4,9,12-tetraazacyclohexadecane-2,11-dione and subjected to 1,3-cycloadditionreactio

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

Isothiazolinone compound and corresponding application

The invention provides an isothiazolinone compound with an IDO inhibitory activity, and a preparing method and pharmaceutical application thereof. The invention particularly relates to a compound shown in a formula I, pharmaceutically acceptable salts thereof, isomers and prodrugs, wherein definitions of all groups are shown in the description. The invention further relates to compound drug preparations, drug compositions and the application of the compound drug preparations and the drug compositions in treating, relieving and/or preventing various relevant diseases caused by immunosuppressionsuch as tumors, virus infection or autoimmune diseases. The isothiazolinone compound has the excellent IDO inhibitory activity.

Design, synthesis and biological evaluation of novel 2,3-indolinedione derivatives against mantle cell lymphoma

2,3-Indolinedione derivatives have been identified as a novel class of promising agents for cancer treatment. In this study, eighteen 2,3-indolinedione derivatives were designed and synthesized, and their anticancer activities against mantle cell lymphoma (MCL) cells were evaluated. Most of them exhibited significant antiproliferative activity against the tested cell lines, and compound K5 was the most potent (MCL cellular IC50 = 0.4–0.7 μM). Further, compound K5 could induce cell apoptosis and cell cycle arrest in G2/M phase. Additionally, the results of drug-likeness analysis demonstrated that these novel 2,3-indolinedione derivatives could have potential as novel treatment strategies for MCL.

Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpro

Synthesis and electrochemical and antioxidant properties of chalcogenocyanate oxadiazole and 5-heteroarylchalcogenomethyl-1: H -tetrazole derivatives

This article presents the chalcogenocyanate oxadiazoles 7 and 8 and their derivatives 5-heteroarylchalcogenomethyl-1H-tetrazoles 9 and 10, which were synthesized in high yields. The 5-substituted-1H-tetrazoles were obtained via [3+2] cycloaddition reactions of chalcogenocyanates 7 and 8 with sodium azide (NaN3) using a simple methodology. All the obtained compounds were characterized by NMR and high resolution mass spectrometry analysis. Their in vitro antioxidant activity was evaluated by measuring their ability to eliminate free radicals in the form of 2,2-diphenyl-2-picrylhydrazyl (DPPH) and through the reduction of molybdenum(vi) to molybdenum(v). The results for the phosphomolybdenum method indicated that some compounds have antioxidant properties, as evidenced by electrochemical oxidation tests to which they were subjected, which correlate their oxidation potentials (Epa) with their activity values (EC50).

Design, microwave assisted synthesis and characterization of substituted 1,2,4-oxadiazole analogues as promising pharmacological agents

Microwave assisted synthesis of a series of 3,5-disubstituted-1,2,4-oxadiazole analogues (3a-j) has been achieved between 5-(chloromethyl)-3-substituted phenyl-1,2,4-oxadiazoles (2a-j) and substituted benzophenone in presence of potassium carbonate in ace

Discovery and preliminary evaluation of 2-aminobenzamide and hydroxamate derivatives containing 1,2,4-oxadiazole moiety as potent histone deacetylase inhibitors

Using Entinostat as a lead compound, 2-aminobenzamide and hydroxamate derivatives have been designed and synthesized. The entire target compounds were investigated for their in vitro antiproliferative activities using the MTT-based assay against five human cancer cell lines including U937, A549, NCI-H661, MDA-MB-231 and HCT116. 2-Aminobenzamide series of compounds (10a-10j) demonstrated the most significant inhibition against human acute monocytic myeloid leukemia cell line U937, but no or poor activities against two human lung cancer cell lines. Furthermore, the target compounds were screened for their inhibitory activities against HDAC 1, 2, and 8. 2-Aminobenzamide derivatives (10) manifested a higher selectivity for HDAC 1 over HDAC 2, but were not active against HDAC 8. In contrast, most hydroxamate derivatives (11) inhibit HDAC 8 with lower IC50 values than SAHA and Entinostat. Docking study with selected compounds 10f and 11a revealed that the compounds might bind tightly to the binding pockets in HDAC 2 and HDAC 8, respectively. The results suggest that they may be promising lead compounds for the development of novel anti-tumor drug potentially via inhibiting HDACs.