2-Bromo-6-methoxybenzene-1,4-diol

Base Information

• Chemical Name: 2-Bromo-6-methoxybenzene-1,4-diol
• CAS No.: 61654-67-9
• Molecular Formula: C7H7BrO3
• Molecular Weight: 219.035
• ChEMBL ID: CHEMBL4742702
• DSSTox Substance ID: DTXSID80404042
• Wikidata: Q82208004
• Mol file: 61654-67-9.mol

Synonyms:2-bromo-6-methoxybenzene-1,4-diol;61654-67-9;1,4-Benzenediol, 2-bromo-6-methoxy-;CHEMBL4742702;ghl.PD_Mitscher_leg0.1017;SCHEMBL18585967;DTXSID80404042;BDBM50555915;AKOS024342150;CS-0226966;2-BROMO-6-METHOXY-BENZENE-1,4-DIOL

Chemical Property of 2-Bromo-6-methoxybenzene-1,4-diol

Chemical Property:

• PSA: 49.69000
• LogP: 1.86890
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 217.95786
• Heavy Atom Count: 11
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

2-BROMO-6-METHOXY-BENZENE-1,4-DIOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=CC(=C1)O)Br)O
• Uses: 2-Bromo-6-methoxybenzene-1,4-diol is an intermediate in the synthesis of Endophenazine B (E555485), a new phenazine antibiotic isolated from the arthropod associated endosymbiont Streptomyces anulatus and shows antimicrobial activities against Gram-positive bacteria and some filamentous fungi, and herbicidal activity against Lemna minor (duckweed).

Technology Process of 2-Bromo-6-methoxybenzene-1,4-diol

There total 4 articles about 2-Bromo-6-methoxybenzene-1,4-diol 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: 92.0%

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → 2,5-dihydroxy-3-methoxy-1-bromobenzene (61654-67-9)

Guidance literature:

With potassium hydroxide; dihydrogen peroxide;

DOI:10.1016/S0040-4039(00)60137-5

Reference yield:

vanillin (121-33-5,8014-42-4) → 2,5-dihydroxy-3-methoxy-1-bromobenzene (61654-67-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Br₂ / methanol / 20 °C

2: H₂O₂; KOH / H₂O / 5.3 h / 90 °C

With potassium hydroxide; dihydrogen peroxide; bromine; In methanol; water; 2: Baeyer-Villiger oxidation;

DOI:10.1021/np060481l

Reference yield:

→ 2,5-dihydroxy-3-methoxy-1-bromobenzene (61654-67-9)

Guidance literature:

With dihydrogen peroxide;

upstream raw materials:

5-bromo-4-hydroxy-3-methoxybenzaldehyde

vanillin

Downstream raw materials:

4,8-dimethylphenanthro[3,2-b]furan-7,11-dione

Tanshinone I

11-benzyl-2-methoxy-1H-benzo[a]carbazole-1,4(11H)-dione

3-bromo-5-methoxy-2-((4-trifluoromethylphenyl)ethyl)cyclohexa-2,5-diene-1,4-dione

Refernces

• 1、 Sisa, Miroslav,Dvorakova, Marcela,Temml, Veronika,Jarosova, Veronika,Vanek, Tomas,Landa, Premysl. "Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core". . . Retrieved 2020/07/31.
• 2、 Tamura, Masafumi,Koshibe, Yuhei,Kaji, Kiho,Ueda, Jun-Ya,Shirataki, Yoshiaki. "Attempt to synthesize 2,3,5,4′-tetrahydroxystilbene derived from 2,3,5,4′-tetrahydroxystilbene-2-O-β-glucoside (THSG)". . p. 122 - 125. Retrieved 2015/02/19.