[4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid

Base Information

• Chemical Name: [4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid
• CAS No.: 276694-22-5
• Molecular Formula: C8H7BN2O3
• Molecular Weight: 189.966
• DSSTox Substance ID: DTXSID30436878
• Wikidata: Q82252222
• Mol file: 276694-22-5.mol

Synonyms:276694-22-5;[4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid;(4-(1,3,4-Oxadiazol-2-yl)phenyl)boronic acid;4-(1,3,4-Oxadiazol-2-ylphenyl)boronic acid;Boronic acid, [4-(1,3,4-oxadiazol-2-yl)phenyl]-;SCHEMBL1727566;DTXSID30436878;WXOMKINBRCKWNI-UHFFFAOYSA-N;ODZ101336;AT32988;SB17876;CS-0188866;4-(1,3,4-oxadiazol-2-yl)phenylboronic acid;(4-(1,3,4-Oxadiazol-2-yl)phenyl)boronicacid

Chemical Property of [4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid

Chemical Property:

• PSA: 79.38000
• LogP: -0.58360
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 190.0549723
• Heavy Atom Count: 14
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

[4-(1,3,4-Oxadiazol-2-yl)phenyl]boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of [4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid

There total 4 articles about [4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid 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: 88.0%

2-(4-bromophenyl)-1,3,4-oxadiazole (41420-90-0) → [4-(1,3,4-oxadiazol-2-yl) phenyl]boronic acid (276694-22-5)

Guidance literature:

2-(4-bromophenyl)-1,3,4-oxadiazole; With p-tolyllithium; In tetrahydrofuran; at -65 ℃; for 0.5h;

With n-hexyllithium; In tetrahydrofuran; hexanes; at -65 ℃; for 0.5h;

With Triisopropyl borate; water; acetic acid; more than 3 stages; Product distribution / selectivity;

Reference yield: 82.0%

2-(4-bromophenyl)-1,3,4-oxadiazole (41420-90-0) + Triisopropyl borate (5419-55-6) → [4-(1,3,4-oxadiazol-2-yl) phenyl]boronic acid (276694-22-5)

Guidance literature:

2-(4-bromophenyl)-1,3,4-oxadiazole; With methyllithium; In tetrahydrofuran; formaldehyde diethyl acetal; at -65 ℃; for 1h;

With n-butyllithium; In tetrahydrofuran; hexanes; formaldehyde diethyl acetal; at -65 ℃; for 1h;

Triisopropyl borate; With acetic acid; more than 3 stages;

Reference yield: 81.0%

2-(4-bromophenyl)-1,3,4-oxadiazole (41420-90-0) + Trimethyl borate (121-43-7,63156-11-6) + water (7732-18-5) → [4-(1,3,4-oxadiazol-2-yl) phenyl]boronic acid (276694-22-5)

Guidance literature:

2-(4-bromophenyl)-1,3,4-oxadiazole; With n-butyllithium; In tetrahydrofuran; hexane; at -40 - 0 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 5h; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; hexane; for 1h; Inert atmosphere;

upstream raw materials:

2-(4-bromophenyl)-1,3,4-oxadiazole

Triisopropyl borate

Trimethyl borate

water

Downstream raw materials:

potassium 4-(1,3,4-oxadiazol-2-yl)phenyltrifluoroborate

Refernces

• 1、 Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.,Dreher, Spencer D.,Tudge, Matthew T.. "Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid". supporting information; experimental part. p. 11667 - 11673. Retrieved 2012/09/05.
• 2、 -. "CHEMICAL PROCESS". Page/Page column 11-12. . Retrieved 2008/06/13.