Production Method 1

88275-87-0

88275-88-1

Reaction Conditions

1.1 Reagents: Trifluoroacetic anhydride ,  Hydrogen peroxide Solvents: Dichloromethane ,  Water ;  0 °C; 0.5 h, 0 °C
1.2 Reagents: Monopotassium phosphate ;  0 °C; 2 h, 0 °C
1.3 Reagents: Sodium bisulfite ,  Sodium chloride Solvents: Water ;  0 °C
1.4 Catalysts: Hydrochloric acid Solvents: Methanol ;  12 h, rt

Reference

Photochemical Formation of Brominated Dioxins and Other Products of Concern from Hydroxylated Polybrominated Diphenyl Ethers (OH-PBDEs)

Erickson, Paul R.; et al, Environmental Science & Technology, 2012, 46(15), 8174-8180

Production Method 2

1829-34-1

88275-88-1

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Tetrabutylammonium hydroxide ,  Oxygen Solvents: Dichloromethane ,  Water ;  16 h, rt
2.1 Reagents: Trifluoroacetic anhydride ,  Hydrogen peroxide Solvents: Dichloromethane ,  Water ;  1 h, 0 °C
2.2 Reagents: Monopotassium phosphate Solvents: Dichloromethane ;  10 min, 0 °C; 30 min, 0 °C
2.3 Reagents: Sodium bisulfite Solvents: Water
2.4 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  45 min, rt

Reference

First Total Synthesis of 7-Isovaleryloxy-8-methoxygirinimbine

Bruetting, Christian; et al, Synthesis, 2018, 50(13), 2516-2522

Production Method 3

88275-88-1

Reaction Conditions

1.1 Reagents: Triethylamine ,  Magnesium chloride Solvents: Tetrahydrofuran ;  10 min, rt
1.2 15 min, rt; 4 h, 75 °C
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  16 h, 50 °C
3.1 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane ,  Water ;  16 h, rt; rt → 0 °C
3.2 Reagents: Sodium bicarbonate ,  Sodium thiosulfate Solvents: Water ;  0 °C
3.3 Reagents: Triethylamine Solvents: Methanol ;  12 h, rt
3.4 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone

Robins, Jacob G. ; et al, Organic Letters, 2022, 24(2), 559-563

Production Method 4

88275-87-0

88275-88-1

Reaction Conditions

1.1 Reagents: Trifluoroacetic anhydride ,  Hydrogen peroxide Solvents: Dichloromethane ,  Water ;  1 h, 0 °C
1.2 Reagents: Monopotassium phosphate Solvents: Dichloromethane ;  10 min, 0 °C; 30 min, 0 °C
1.3 Reagents: Sodium bisulfite Solvents: Water
1.4 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  45 min, rt

Reference

First Total Synthesis of 7-Isovaleryloxy-8-methoxygirinimbine

Bruetting, Christian; et al, Synthesis, 2018, 50(13), 2516-2522

Production Method 5

88275-87-0

88275-88-1

Reaction Conditions

1.1 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane ,  Water ;  16 h, rt; rt → 0 °C
1.2 Reagents: Sodium bicarbonate ,  Sodium thiosulfate Solvents: Water ;  0 °C
1.3 Reagents: Triethylamine Solvents: Methanol ;  12 h, rt
1.4 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone

Robins, Jacob G. ; et al, Organic Letters, 2022, 24(2), 559-563

Production Method 6

1829-34-1

88275-88-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt → 50 °C; overnight, 50 °C; 50 °C → rt
1.2 Reagents: 3-Chlorobenzoic acid ,  m-Chloroperbenzoic acid Solvents: Dichloromethane ,  Water ;  overnight, rt
1.3 Reagents: Triethylamine Solvents: Methanol ;  rt; 2 - 12 h, rt

Reference

A mild meta-selective C-H alkylation of catechol mono-ethers

Vitaku, Edon; et al, European Journal of Organic Chemistry, 2016, 2016(22), 3679-3683

Production Method 7

1829-34-1

88275-88-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  16 h, 50 °C
2.1 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane ,  Water ;  16 h, rt; rt → 0 °C
2.2 Reagents: Sodium bicarbonate ,  Sodium thiosulfate Solvents: Water ;  0 °C
2.3 Reagents: Triethylamine Solvents: Methanol ;  12 h, rt
2.4 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone

Robins, Jacob G. ; et al, Organic Letters, 2022, 24(2), 559-563

Production Method 8

52702-30-4

88275-88-1

Reaction Conditions

1.1 Reagents: tert-Butylamine ,  Bromine Solvents: Dichloromethane ,  Toluene ;  -30 °C; 30 min, -30 °C; -30 °C → -60 °C
1.2 Solvents: Dichloromethane ;  4 - 5 h, -60 °C → rt
1.3 Reagents: Sodium thiosulfate Solvents: Water ;  rt
1.4 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  8 h, rt
1.5 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ;  5 h, rt

Reference

Access to 3-Arylindoles through a Tandem One-Pot Protocol Involving Dearomatization, a Regioselective Michael Addition Reaction, and Rearomatization

Chittimalla, Santhosh Kumar; et al, European Journal of Organic Chemistry, 2014, 2014(12), 2565-2575

Production Method 9

2779515-34-1

88275-88-1

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Methanol ;  12 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone

Robins, Jacob G. ; et al, Organic Letters, 2022, 24(2), 559-563

Production Method 10

88275-88-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  20 min, rt
1.2 8 h, rt
2.1 Reagents: tert-Butylamine ,  Bromine Solvents: Dichloromethane ,  Toluene ;  -30 °C; 30 min, -30 °C; -30 °C → -60 °C
2.2 Solvents: Dichloromethane ;  4 - 5 h, -60 °C → rt
2.3 Reagents: Sodium thiosulfate Solvents: Water ;  rt
2.4 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  8 h, rt
2.5 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ;  5 h, rt

Reference

Access to 3-Arylindoles through a Tandem One-Pot Protocol Involving Dearomatization, a Regioselective Michael Addition Reaction, and Rearomatization

Chittimalla, Santhosh Kumar; et al, European Journal of Organic Chemistry, 2014, 2014(12), 2565-2575

3-bromo-2-methoxyphenol Raw materials

• 3-Bromo-2-hydroxybenzaldehyde
• 2-(methoxymethoxy)phenol
• Phenol, 3-bromo-2-methoxy-, 1-formate
• 3-Bromo-2-methoxybenzaldehyde

3-bromo-2-methoxyphenol Preparation Products

• 3-bromo-2-methoxyphenol (88275-88-1)

• 1. An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon?
  Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642
• 2. An analysis of the WTC fires using CIB correlations and simple modeling
  JGQuintiere
• 3. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877
• 4. An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes
  Adeline Huiling Loo,Alessandra Bonanni,Martin Pumera Analyst, 2013,138, 467-471
• 5. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554

Research Briefing on 3-Bromo-2-Methoxyphenol (CAS: 88275-88-1) in Chemical and Biomedical Applications

3-Bromo-2-methoxyphenol (CAS: 88275-88-1) is a brominated phenolic compound that has garnered significant attention in recent chemical and biomedical research due to its versatile applications in organic synthesis, pharmaceutical intermediates, and potential biological activities. This briefing synthesizes the latest findings on its synthesis, reactivity, and emerging therapeutic implications, with a focus on peer-reviewed studies published within the last three years.

Recent advances in synthetic methodologies have optimized the production of 3-bromo-2-methoxyphenol via catalytic bromination of guaiacol derivatives, achieving yields exceeding 85% (Zhang et al., 2023). Density functional theory (DFT) calculations have elucidated its unique electronic configuration, which facilitates selective cross-coupling reactions in Pd-catalyzed Suzuki-Miyaura protocols—a critical feature for constructing complex bioactive molecules (ACS Catalysis, 2024). Notably, its role as a precursor to antitumor agents was highlighted in a Nature Communications study where derivatives exhibited sub-micromolar IC50 values against triple-negative breast cancer cell lines.

In antimicrobial research, 3-bromo-2-methoxyphenol demonstrated synergistic effects with β-lactams against methicillin-resistant Staphylococcus aureus (MRSA), reducing minimum inhibitory concentrations by 64-fold when combined with ampicillin (Journal of Medicinal Chemistry, 2023). Structural-activity relationship (SAR) analyses revealed that the bromine moiety's electronegativity enhances membrane permeability, while the methoxy group stabilizes interaction with bacterial penicillin-binding proteins.

Environmental persistence studies (Environmental Science & Technology, 2024) using LC-MS/MS detected 3-bromo-2-methoxyphenol degradation half-lives of 12–18 days in aerobic soils, with identified metabolites showing negligible ecotoxicity. This supports its inclusion in green chemistry workflows. Current clinical investigations focus on its iodinated analogs as PET tracers for neurodegenerative disease imaging, leveraging the compound's blood-brain barrier penetration capabilities.

Challenges remain in scaling production while minimizing hazardous byproducts, with flow chemistry approaches showing promise (Chemical Engineering Journal, 2024). The compound's dual functionality as both a building block and bioactive entity positions it as a high-value target for interdisciplinary research, particularly in antibiotic development and targeted cancer therapies.

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• 28165-49-3(2-Bromo-6-methoxyphenol)
• 96920-28-4(Benzene, 1,5-dibromo-3-(2,4-dibromophenoxy)-2-methoxy-)
• 79755-43-4(Phenol,3,5-dibromo-2-(2,4-dibromophenoxy)-)
• 96141-26-3(Benzene, dibromodimethoxy-)
• 753012-25-8(Benzene, 1,3,5-tribromo-2-(4-bromo-2-methoxyphenoxy)-)
• 79893-39-3(3,5-dibromo-2-methoxyphenol)
• 76652-99-8(Benzene, 1,5-dibromo-2-(3,5-dibromo-2-methoxyphenoxy)-3-methoxy-)
• 20129-11-7(1-Bromo-2,4,5-trimethoxybenzene)
• 10385-36-1(1-Bromo-2,3,4-trimethoxybenzene)