2-Phenyl-1,3,4-oxadiazole

Base Information

• Chemical Name: 2-Phenyl-1,3,4-oxadiazole
• CAS No.: 825-56-9
• Molecular Formula: C8H6N2O
• Molecular Weight: 146.148
• Hs Code.: 2934999090
• European Community (EC) Number: 879-121-3
• NSC Number: 94884
• DSSTox Substance ID: DTXSID80231799
• Nikkaji Number: J65.681J
• Wikidata: Q72498001
• ChEMBL ID: CHEMBL2269004
• Mol file: 825-56-9.mol

Synonyms:2-Phenyl-1,3,4-oxadiazole;825-56-9;1,3,4-OXADIAZOLE, 2-PHENYL-;2-Phenyl-[1,3,4]oxadiazole;NSC 94884;2-Fenil-1,3,4-ossadiazolo [Italian];BRN 0118804;2-Fenil-1,3,4-ossadiazolo;4-27-00-07140 (Beilstein Handbook Reference);NSC94884;EC-000.1752;SCHEMBL9555;2-Phenyl-1,3,4-oxadiazol;1,4-Oxadiazole, 2-phenyl-;5-phenyl-1,3,4-oxadiazole;2-phenyl-[1.3.4]oxadiazole;CHEMBL2269004;2-phenyl-[1,3,4]-oxadiazole;2-phenyl-[1.3.4]-oxadiazole;DTXSID80231799;CEVIMELINE,HYDROCHLORIDESALT;BCP27494;MFCD00491613;NSC-94884;ODZ101337;STK408136;AKOS002300438;AS-58422;LS-99168;AM20041210;BB 0238235;CS-0119950;FT-0691831;EN300-44953;2-Phenyloxadiazole;5-Phenyl-1,3,4-Oxadiazole;D71189;Z55670800

Chemical Property of 2-Phenyl-1,3,4-oxadiazole

Chemical Property:

• Vapor Pressure: 0.0286mmHg at 25°C
• Melting Point: 34 °C
• Boiling Point: 253.8°Cat760mmHg
• PKA: -4.52±0.32(Predicted)
• Flash Point: 111°C
• PSA: 38.92000
• Density: 1.179g/cm³
• LogP: 1.73660
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 146.048012819
• Heavy Atom Count: 11
• Complexity: 123

Purity/Quality:

97% ^*data from raw suppliers

2-phenyl-1,3,4-oxadiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NN=CO2

Technology Process of 2-Phenyl-1,3,4-oxadiazole

There total 79 articles about 2-Phenyl-1,3,4-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: 97.0%

N-isocyaniminotriphenylphosphorane (73789-56-7) + benzoic acid (65-85-0,8013-63-6) → 2-phenyl-1,3,4-oxadiazole (825-56-9)

Guidance literature:

In dichloromethane; at 20 ℃; for 0.166667h; Time; Solvent; Sonication;

DOI:10.1016/j.ultsonch.2013.06.009

Reference yield: 97.0%

benzoic acid hydrazide (613-94-5) + orthoformic acid triethyl ester (122-51-0) → 2-phenyl-1,3,4-oxadiazole (825-56-9)

Guidance literature:

for 12h; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02365

Reference yield: 93.0%

sodium chlorodifluoroacetate (1895-39-2) + benzoic acid hydrazide (613-94-5) → 2-phenyl-1,3,4-oxadiazole (825-56-9)

Guidance literature:

With potassium phosphate; In acetonitrile; at 100 ℃; for 1h; Reagent/catalyst; Solvent; Mechanism; Sealed tube; Inert atmosphere;

DOI:10.1016/j.cclet.2021.08.089

upstream raw materials:

diethyl ether

Benzoyl bromide

diazo-methane; diazomethyl lithium

benzoic acid ethyl ester

Downstream raw materials:

phenyl-1,3,4-thiadiazole

2-phenyl-1,3,4-thiadiazole-5(4H)-thione

{1-[(R/S)-hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-methylbutyl}carbamic acid tert-butyl ester

5-iodo-2-phenyl-[1,3,4]oxadiazole

Refernces

Direct heteroarylation of tautomerizable heterocycles into unsymmetrical and symmetrical biheterocycles via Pd/Cu-catalyzed phosphonium coupling

10.1021/ol300455e

The research explores a novel method for synthesizing biheterocyclic compounds. The purpose of this study is to develop a direct and efficient route for the cross-coupling of tautomerizable heterocycles with unfunctionalized heteroarenes, aiming to create a variety of biologically active and functionally important biheterocyclic frameworks. The key chemicals used in this research include tautomerizable heterocycles such as 2-methyl-1H-pyridazine-3,6-dione, heteroarenes like 2-phenyl-1,3,4-oxadiazole, and catalysts such as Pd(OAc)2 and CuI. The methodology involves PyBroP-mediated activation of the heterocycles to form phosphonium salts, followed by Pd/Cu-catalyzed coupling reactions. The study concludes that this approach allows for the facile synthesis of both unsymmetrical and symmetrical biheterocyclic compounds, including diazine-azole and bidiazine units, using readily available substrates. This method provides a significant advancement in the synthesis of biheterocyclic compounds, offering a more direct and efficient route compared to traditional multi-step processes.