1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl N-phenylcarbamate

Base Information

• Chemical Name: 1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl N-phenylcarbamate
• CAS No.: 1222010-52-7
• Molecular Formula: C₁₄H₁₂BNO₄
• Molecular Weight: 269.065
• DSSTox Substance ID: DTXSID601160724
• ChEMBL ID: CHEMBL1688742
• Mol file: 1222010-52-7.mol

Synonyms:SCHEMBL2280834;CHEMBL1688742;HNPFYPHRCXNEGX-UHFFFAOYSA-N;DTXSID601160724;1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl N-phenylcarbamate;2,1-Benzoxaborol-6-ol, 1,3-dihydro-1-hydroxy-, 6-(N-phenylcarbamate);1222010-52-7

Chemical Property of 1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl N-phenylcarbamate

Chemical Property:

• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 269.0859380
• Heavy Atom Count: 20
• Complexity: 348

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(C2=C(CO1)C=CC(=C2)OC(=O)NC3=CC=CC=C3)O

Technology Process of 1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl N-phenylcarbamate

There total 9 articles about 1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl N-phenylcarbamate 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: 18.0%

6-hydroxyl-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1196473-37-6) + phenyl isocyanate (103-71-9) → 1,3-dihydro-1-hydroxy-2,2-benzoxaborol-6-yl N-phenylcarbamate (1222010-52-7)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Inert atmosphere; Cooling;

DOI:10.1021/jm101225g

Reference yield:

2-bromo-4-fluorobenzaldehyde (59142-68-6) → 1,3-dihydro-1-hydroxy-2,2-benzoxaborol-6-yl N-phenylcarbamate (1222010-52-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 65 °C / Cooling; Inert atmosphere

3.1: n-butyllithium; Triisopropyl borate / tetrahydrofuran / -80 - 20 °C / Inert atmosphere

3.2: 2 h

4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C

5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

6.1: triethylamine / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere; Cooling

With sodium tetrahydroborate; n-butyllithium; Triisopropyl borate; palladium 10% on activated carbon; hydrogen; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/jm101225g

Reference yield:

6-benzyloxy-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1222010-47-0) → 1,3-dihydro-1-hydroxy-2,2-benzoxaborol-6-yl N-phenylcarbamate (1222010-52-7)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

2: triethylamine / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere; Cooling

With palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm101225g

upstream raw materials:

6-hydroxyl-1,3-dihydro-1-hydroxy-2,1-benzoxaborole

phenyl isocyanate

2-(2-bromo-4-fluorophenyl)-1,3-dioxolane

C₁₆H₁₅BrO₃

Refernces

• 1、 -. "BORON-CONTAINING SMALL MOLECULES AS ANTI-PROTOZOAL AGENTS". Page/Page column 154. . Retrieved 2010/04/30.