1,2,4-Oxadiazole

Base Information

• Chemical Name: 1,2,4-Oxadiazole
• CAS No.: 288-90-4
• Molecular Formula: C2H2 N2 O
• Molecular Weight: 70.05
• DSSTox Substance ID: DTXSID90182985
• Nikkaji Number: J5.456I
• Wikidata: Q56054487
• Mol file: 288-90-4.mol

Synonyms:1,2,4-Oxadiazole;Azoxime;2,4-Diazafuran;288-90-4;DTXSID90182985;BBVIDBNAYOIXOE-UHFFFAOYSA-N

Chemical Property of 1,2,4-Oxadiazole

Chemical Property:

• Vapor Pressure: 86.5mmHg at 25°C
• Melting Point: 69-70 °C(Solv: ethanol (64-17-5))
• Boiling Point: 82.7°C at 760 mmHg
• PKA: -0.28±0.20(Predicted)
• Flash Point: 12.9°C
• PSA: 38.92000
• Density: 1.193g/cm³
• LogP: 0.06960
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 70.016712692
• Heavy Atom Count: 5
• Complexity: 30.8

Purity/Quality:

99% ^*data from raw suppliers

1,2,4-Oxadiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NOC=N1
• Description: 1,2,4-Oxadiazole is a five-membered, planar, conjugated, nonbenzonoid, aromatic heterocyclic system comprised of one oxygen atom and two nitrogen atoms at positions 2 and 4 of the oxadiazole ring. The oxadiazole ring has two pyridine-like nitrogen atoms. Positions 3 and 5 are vulnerable for nucleophilic substitution to form 3,5-disubstituted 1,2,4-oxadiazoles. The topography of the 1,2,4-oxadiazole ring reveals that it has a more heterodiene character compared to its aromatic nature. The substituted 1,2,4-oxadiazole ring system was first reported in 1880 but the parent 1,2,4-oxadiazole was not reported until 1962 because of instability of the molecule.
• Physical properties: The parent 1H-1,2,4-oxadiazole is highly unstable and its synthesis has not been reported so far. The 3,5-disubstituted 1,2,4-oxadiazoles are stable, while monosubstituted oxadiazoles are less stable and prone to acid- and base-induced hydrolysis. The 13C NMR spectra of 3,5-diaryl-1,2,4-oxadiazoles in CDCl3 showed chemical shift for C3 at 168.8–169.0 ppm and C5 at 174.7–175.8 ppm.
• Uses: 1,2,4-Oxadiazole can be used in biological study of antitubercular activity of butyrate-specific oxadiazoles against Mycobacterium tuberculosis and their cytotoxicity on monkey kidney cells.

Technology Process of 1,2,4-Oxadiazole

There total 8 articles about 1,2,4-Oxadiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

→ 1,3,5-oxdiazole (288-90-4) + (S)-{{5-[1-(2-Benzoylphenyl)amino]-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}ethyl}}-3-propyl-1,2,4-oxadiazole (329981-60-4)

Guidance literature:

Reference yield: 50.0%

Monomethyl terephthalate (1679-64-7) → 1,3,5-oxdiazole (288-90-4)

Guidance literature:

With benzotriazol-1-ol; triethylamine; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

Reference yield: 45.0%

→ 1,3,5-oxdiazole (288-90-4) + (S)-{{5-[1-(2-Benzoylphenyl)amino]-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}ethyl}}-3-ethyl-1,2,4-oxadiazole (329981-62-6)

Guidance literature:

upstream raw materials:

Monomethyl terephthalate

Refernces

Reaction of oximes of-diketones with diphosphorous tetraiodide for preparation of oxadiazoles and nitriles

10.1080/00397911.2011.595035

The study primarily investigates the use of diphosphorus tetraiodide (P2I4) as a novel and mild condensing agent for the synthesis of oxadiazoles and nitriles from the oximes of α-diketones. The research explores the dehydration of oximes to form 1,2,5-oxadiazoles and the rearrangement of oximes to produce the normal Beckmann product, 1,2,4-oxadiazole. Key chemicals used in the study include dioximes derived from α-diketones, such as benzildioxime, and various substituted 1,2-dioximes, which serve as substrates for the synthesis of oxadiazoles. The study also examines the effects of different solvents on the reaction, with chlorinated solvents, particularly dichloromethane, proving to be the most effective. The purpose of these chemicals is to facilitate the synthesis of oxadiazoles, which are an important class of heterocycles used in a variety of bioactive molecules, and nitriles, through a simple and efficient method.

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