Benzo[C][1,2,5]Oxadiazole-5-Boronic Acid

Base Information

• Chemical Name: Benzo[C][1,2,5]Oxadiazole-5-Boronic Acid
• CAS No.: 426268-09-9
• Molecular Formula: C6H5BN2O3
• Molecular Weight: 163.928
• ChEMBL ID: CHEMBL4082284
• DSSTox Substance ID: DTXSID30405428
• Nikkaji Number: J1.676.689E
• Wikidata: Q82209975
• Mol file: 426268-09-9.mol

Synonyms:426268-09-9;Benzo[c][1,2,5]oxadiazol-5-ylboronic acid;Benzo[C][1,2,5]Oxadiazole-5-Boronic Acid;2,1,3-benzoxadiazol-5-ylboronic acid;CHEMBL4082284;(2,1,3-BENZOXADIAZOL-5-YL)BORONIC ACID;MFCD07186239;SCHEMBL439914;DTXSID30405428;CHYMBQMSEFLESI-UHFFFAOYSA-N;BDBM50266946;AKOS004116042;5-benzo[1,2,5]oxadiazoleboronic acid;AB30565;CS-W005986;DS-2004;benzo[1,2,5]oxadiazole-5-boronic acid;SY104192;5-Benzo[c][1,2,5]oxadiazoleboronic Acid;B-2,1,3-benzoxadiazol-5-yl-boronic acid;benzo[1,2,5]oxadiazol-5-yl-boronic acid;FT-0751571;EN300-151216;A825968;Benzo[c][1 pound not2 pound not5]oxadiazol-5-ylboronic acid

Chemical Property of Benzo[C][1,2,5]Oxadiazole-5-Boronic Acid

Chemical Property:

• Boiling Point: 374.7 °C at 760 mmHg
• PKA: 6.36±0.30(Predicted)
• Flash Point: 180.4 °C
• PSA: 79.38000
• Density: 1.49 g/cm³
• LogP: -1.09740
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 164.0393222
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzo[c][1,2,5]oxadiazol-5-ylboronic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B(C1=CC2=NON=C2C=C1)(O)O

Technology Process of Benzo[C][1,2,5]Oxadiazole-5-Boronic Acid

There total 5 articles about Benzo[C][1,2,5]Oxadiazole-5-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: 45.0%

5-bromo-benzo[1,2,5]oxadiazole (51376-06-8) → benzo[c][1,2,5]oxadiazole-5-boronic acid (426268-09-9)

Guidance literature:

With n-butyllithium; triethyl borate; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; pentane; at -100 ℃; for 0.0833333h;

DOI:10.1016/S0960-894X(01)00720-X

Reference yield: 34.0%

5-bromo-benzo[1,2,5]oxadiazole (51376-06-8) + triethyl borate (150-46-9) → benzo[c][1,2,5]oxadiazole-5-boronic acid (426268-09-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -90 - -80 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/op025615q

Reference yield:

4-Bromo-2-nitroaniline (875-51-4) → benzo[c][1,2,5]oxadiazole-5-boronic acid (426268-09-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: KOH / ethanol / 1 h / 60 °C

1.2: aq. NaOCl / 1 h / 0 °C

2.1: PPh₃ / xylene / 3 h / 140 °C

3.1: 45 percent / n-BuLi; TMEDA; B(OEt)3 / tetrahydrofuran; pentane / 0.08 h / -100 °C

With potassium hydroxide; n-butyllithium; triethyl borate; N,N,N,N,-tetramethylethylenediamine; triphenylphosphine; In tetrahydrofuran; ethanol; xylene; pentane;

DOI:10.1016/S0960-894X(01)00720-X

upstream raw materials:

5-bromo-benzo[1,2,5]oxadiazole

4-Bromo-2-nitroaniline

2-nitro-aniline

6-bromobenzo[c][1,2,5]oxadiazole 1-oxide

Downstream raw materials:

5-(5-(p-tolyl)thiophene-2-yl)benzo[c][1,2,5]oxadiazole

3-benzo[1,2,5]oxadiazol-5-yl-1-benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

ethyl 2-(3-benzo[c][1,2,5]oxadiazol-5-yl)-5-(4-(trifluoromethyl)benzyloxy)phenyl-4-methylpentanoate

methyl 2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-5-(2,2,2-trifluoroethoxy)phenyl)-3-cyclopropylpropanoate

Refernces

• 1、 Hersperger, Rene,Dawson, Janet,Mueller, Thomas. "Synthesis of 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridine-6-yl)-benzoic acid: A potent and selective phosphodiesterase type 4D inhibitor". . p. 233 - 235. Retrieved 2007/10/03.