Diazaborine

Base Information

• Chemical Name: Diazaborine
• CAS No.: 22959-81-5
• Molecular Formula: C14H13BN2O3S
• Molecular Weight: 300.146
• UNII: YEB3W2L5P3
• DSSTox Substance ID: DTXSID201148398
• Nikkaji Number: J886.636H
• Wikipedia: Diazaborine_B
• Wikidata: Q5272194
• Metabolomics Workbench ID: 151409
• ChEMBL ID: CHEMBL168634
• Mol file: 22959-81-5.mol

Synonyms:diazaborine;Diazaborine B;YEB3W2L5P3;UNII-YEB3W2L5P3;CHEBI:83945;2-(TOLUENE-4-SULFONYL)-2H-BENZO[D][1,2,3]DIAZABORININ-1-OL;22959-81-5;1,2-Dihydro-1-hydroxy-2-(p-tosyl)-2,3,1-benzo(E)diazaborine;2,3,1-Benzodiazaborine, 1,2-dihydro-1-hydroxy-2-(p-tolylsulfonyl)-;1,2-Dihydro-1-hydroxy-2-((4-methylphenyl)sulfonyl)-2,3,1-benzodiazaborine;6-Methyl-2-(propylsulfonyl)thieno(3,2-d)(1,2,3)diazaborinin-1(2H)-ol;1,2-Dihydro-1-hydroxy-2-[(4-methylphenyl)sulfonyl]-2,3,1-benzodiazaborine;6-methyl-2-(propylsulfonyl)thieno[3,2-d][1,2,3]diazaborinin-1(2H)-ol;CHEMBL168634;SCHEMBL8063699;DTXSID201148398;1-hydroxy-2-(4-methylphenyl)sulfonyl-2,3,1-benzodiazaborinine;DB08265;Q5272194;1-hydroxy-2-(p-tolylsulfonyl)-2,3,1-benzodiazaborinine;2-[(4-methylphenyl)sulfonyl]-2,3,1-benzodiazaborinin-1(2H)-ol;1,2-Dihydro-1-hydroxy-3-(4-methylphenylsulfonyl)-2,4,1-benzo[e]diazaborine

Chemical Property of Diazaborine

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 300.0739936
• Heavy Atom Count: 21
• Complexity: 497

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(C2=CC=CC=C2C=NN1S(=O)(=O)C3=CC=C(C=C3)C)O

Technology Process of Diazaborine

There total 5 articles about Diazaborine 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: 93.0%

Trimethyl borate (121-43-7,63156-11-6) + p-toluenesulfonylhydrazone of 2-bromobenzaldehyde → 1,2-dihydro-1-hydroxy-2-(4-methylbenzenesulfonyl)-2,3,1,-benzodiazaborine (22959-81-5)

Guidance literature:

In not given; according to Sharp, J. T.; Skinner, C. E. D. Tetrahedron Lett. 1986, 27,869-872;

DOI:10.1021/ja963784i

Reference yield: 76.0%

2-formylbenzene boronic acid (40138-16-7) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 1,2-dihydro-1-hydroxy-2-(4-methylbenzenesulfonyl)-2,3,1,-benzodiazaborine (22959-81-5)

Guidance literature:

In ethanol; for 18h; Reflux;

DOI:10.1021/jacs.1c02462

Reference yield:

(5-fluoro-2-formylphenyl)boronic acid (1256355-30-2) → 1,2-dihydro-1-hydroxy-2-(4-methylbenzenesulfonyl)-2,3,1,-benzodiazaborine (22959-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / 24 h / 20 °C

2: ethanol / 18 h / Reflux

In methanol; ethanol;

DOI:10.1021/jacs.1c02462

upstream raw materials:

benzaldehyde p-toluenesulfonylhydrazone

Trimethyl borate

2-formylbenzene boronic acid

toluene-4-sulfonic acid hydrazide

Downstream raw materials:

N’-(2-hydroxybenzylidene)-4-methylbenzene-1-sulfonohydrazide

Refernces

• 1、 Aguiar, Sandra I.,André, Ana S.,António, Jo?o P. M.,Bernardes, Gon?alo J. L.,Carvalho, Joana Inês,Dias, Joana N. R.,Faustino, Hélio,Gois, Pedro M. P.,Lopes, Ricardo M. R. M.,Veiros, Luis F.,da Silva, Frederico A.. "Diazaborines Are a Versatile Platform to Develop ROS-Responsive Antibody Drug Conjugates**". supporting information. p. 25914 - 25921. Retrieved 2021/11/09.
• 2、 Kanichar, Divya,Roppiyakuda, Lance,Kosmowska, Ewa,Faust, Michelle A.,Tran, Kim P.,Chow, Felicia,Buglo, Elena,Groziak, Michael P.,Sarina, Evan A.,Olmstead, Marilyn M.,Silva, Isba,Xu, H. Howard. "Synthesis, characterization, and antibacterial activity of structurally complex 2-Acylated 2,3,1-benzodiazaborines and related compounds". . p. 1381 - 1397. Retrieved 2015/04/14.