Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether

Base Information

• Chemical Name: Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether
• CAS No.: 74849-07-3
• Molecular Formula: C14H10Br4O5
• Molecular Weight: 577.846
• DSSTox Substance ID: DTXSID10434771
• Nikkaji Number: J1.089.245G
• Wikidata: Q82249273
• Metabolomics Workbench ID: 138888
• ChEMBL ID: CHEMBL491516
• Mol file: 74849-07-3.mol

Synonyms:bis(2,3-dibromo-4,5-dihydroxybenzyl) ether

Chemical Property of Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 577.72207
• Heavy Atom Count: 23
• Complexity: 356

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=C(C(=C1O)O)Br)Br)COCC2=CC(=C(C(=C2Br)Br)O)O

Technology Process of Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether

There total 7 articles about Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether 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%

bis(3,4-dihydroxybenzyl) ether → (2-bromo-4,5-dihydroxybenzyl)(2,3-dibromo-4,5-dihydroxybenzyl) ether (1257414-30-4) + 5-((2,3-dibromo-4,5-dihydroxybenzyloxy)methyl)-3,4-dibromobenzene-1,2-diol (74849-07-3)

Guidance literature:

With bromine; acetic acid; at 20 ℃;

DOI:10.1016/j.bmcl.2010.09.015

Reference yield: 21.8%

5,5'-oxybis(methylene)bis(3,4-dibromo-1,2-dimethoxybenzene) (1260106-17-9) → 5-((2,3-dibromo-4,5-dihydroxybenzyloxy)methyl)-3,4-dibromobenzene-1,2-diol (74849-07-3)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃;

DOI:10.3390/md9091554

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → 5-((2,3-dibromo-4,5-dihydroxybenzyloxy)methyl)-3,4-dibromobenzene-1,2-diol (74849-07-3)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / acetonitrile / 4 h / 20 °C

2: bromine / acetic acid / 60 °C

3: sodium tetrahydroborate / methanol / -20 - 20 °C

4: triethylamine; p-toluenesulfonyl chloride / acetonitrile / Reflux

5: boron tribromide / dichloromethane / 0 - 20 °C

With sodium tetrahydroborate; bromine; boron tribromide; potassium carbonate; triethylamine; p-toluenesulfonyl chloride; In methanol; dichloromethane; acetic acid; acetonitrile;

DOI:10.3390/md9091554

upstream raw materials:

5,5'-oxybis(methylene)bis(3,4-dibromo-1,2-dimethoxybenzene)

5-bromo-4-hydroxy-3-methoxybenzaldehyde

(2,3-dibromo-4,5-dimethoxyphenyl)methanol

2,3-dibromo-4,5-dimethoxybenzaldehyde