3-(2-Bromophenyl)-5-phenyl-1,2,4-oxadiazole

Base Information

• Chemical Name: 3-(2-Bromophenyl)-5-phenyl-1,2,4-oxadiazole
• CAS No.: 827332-78-5
• Molecular Formula: C14H9BrN2O
• Molecular Weight: 301.142
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10397857
• Wikidata: Q82199482
• Mol file: 827332-78-5.mol

Synonyms:3-(2-bromophenyl)-5-phenyl-1,2,4-oxadiazole;827332-78-5;DTXSID10397857;CIB33278;MFCD08051773;STK066557;AKOS015835145;BS-25920;CS-0205196;A864355

Chemical Property of 3-(2-Bromophenyl)-5-phenyl-1,2,4-oxadiazole

Chemical Property:

• Boiling Point: 428.8 °C at 760 mmHg
• Flash Point: 213.1 °C
• PSA: 38.92000
• Density: 1.465 g/cm³
• LogP: 4.16610
• Storage Temp.: 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 299.98983
• Heavy Atom Count: 18
• Complexity: 271

Purity/Quality:

≥95% ^*data from raw suppliers

3-(2-Bromophenyl)-5-phenyl-1,2,4-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=NC(=NO2)C3=CC=CC=C3Br

Technology Process of 3-(2-Bromophenyl)-5-phenyl-1,2,4-oxadiazole

There total 5 articles about 3-(2-Bromophenyl)-5-phenyl-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: 60.0%

(Z)-N-benzyl-2-bromo-N'-hydroxybenzimidamide (1452311-06-6) → 3-(2-bromophenyl)-5-phenyl-1,2,4-oxadiazole (827332-78-5)

Guidance literature:

With potassium phosphate; tetrabutylammonium perchlorate; In methanol; at 30 ℃; for 2h; Electrochemical reaction; Green chemistry;

DOI:10.1039/d1ob02040d

Reference yield: 41.0%

o-cyanobromobenzene (2042-37-7) + benzamide (55-21-0,27208-38-4) → 3-(2-bromophenyl)-5-phenyl-1,2,4-oxadiazole (827332-78-5)

Guidance literature:

With copper(l) iodide; 2,9-diphenyl-1,10-phenanthroline; oxygen; potassium carbonate; zinc(II) iodide; In 1,2-dichloro-benzene; at 130 ℃; for 24h; under 760.051 Torr; Schlenk technique; Molecular sieve;

DOI:10.1002/ejoc.201501502

Reference yield:

2-bromobenzaldehyde oxime (34158-72-0,52707-51-4,52707-56-9) → 3-(2-bromophenyl)-5-phenyl-1,2,4-oxadiazole (827332-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1: N-chloro-succinimide / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

2: triethylamine / N,N-dimethyl-formamide / 6 h / 0 - 20 °C / Inert atmosphere

3: potassium phosphate; oxygen / N,N-dimethyl-formamide / 10 h / 60 °C / 760.05 Torr

With potassium phosphate; N-chloro-succinimide; oxygen; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1039/c3ob41393d

upstream raw materials:

2-bromobenzaldehyde oxime

(Z)-N-benzyl-2-bromo-N'-hydroxybenzimidamide

2-bromo N-hydroxybenzimidoyl chloride

ortho-bromobenzaldehyde

Refernces

• 1、 Kuram, Malleswara Rao,Kim, Woo Gyum,Myung, Kyungjae,Hong, Sung You. "Copper-catalyzed direct synthesis of 1,2,4-oxadiazoles from amides and organic nitriles by oxidative N-O bond formation". supporting information. p. 438 - 442. Retrieved 2016/02/19.