61654-67-9

Basic information

• Product Name: 1,4-Benzenediol, 2-bromo-6-methoxy-
• Synonyms: 1,4-Benzenediol,2-bromo-6-methoxy;ghl.PD_Mitscher_leg0.1017
• CAS NO: 61654-67-9
• Molecular Formula: C7H7BrO3
• Molecular Weight: 219.035
• Mol File: 61654-67-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 1,4-Benzenediol, 2-bromo-6-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Benzenediol, 2-bromo-6-methoxy-(61654-67-9)
• EPA Substance Registry System: 1,4-Benzenediol, 2-bromo-6-methoxy-(61654-67-9)

Safety Data

• Hazardous Substances Data: 61654-67-9(Hazardous Substances Data)

Usage

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).

Upstream product

• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 121-33-5 vanillin 

Downstream Products

• 23030-47-9 2-bromo-6-methoxycyclohexa-2,5-diene-1,4-dione 
• 133099-84-0 5-bromo-3-methoxy-1,4-bis(methoxymethoxy)benzene 
• 938175-96-3 C₂₃H₂₃BrO₅ 
• 1032336-00-7 1-bromo-2,3,5-tris(methoxymethoxy)benzene 
• 1601369-91-8 3-bromo-5-methoxy-2-((2-methylphenyl)ethyl)cyclohexa-2,5-diene-1,4-dione 
• 1601369-93-0 3-bromo-5-methoxy-2-phenethylcyclohexa-2,5-diene-1,4-dione 
• 1601369-98-5 3-bromo-2-((4-fluorophenyl)ethyl)-5-methoxycyclohexa-2,5-diene-1,4-dione 
• 1601370-01-7 3-bromo-5-methoxy-2-((4-trifluoromethylphenyl)ethyl)cyclohexa-2,5-diene-1,4-dione 
• 1601370-20-0 11-benzyl-2-methoxy-1H-benzo[a]carbazole-1,4(11H)-dione 
• 568-73-0 Tanshinone I 
• 20958-17-2 4,8-dimethylphenanthro[3,2-b]furan-7,11-dione 
• 1352196-07-6 C₁₉H₃₅BrO₃Si₂ 
• 1352196-35-0 C₂₄H₄₂O₅Si₂ 
• 1321913-84-1 7-benzyl-4-methyl-5-[2-(2,3,5-trimethoxyphenyl)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-2-amine 

Relevant articles and documents

Evaluation of the anti-inflammatory effects of synthesised tanshinone I and isotanshinone I analogues in zebrafish

During inflammation, dysregulated neutrophil behaviour can play a major role in a range of chronic inflammatory diseases, for many of which current treatments are generally ineffective. Recently, specific naturally occurring tanshinones have shown promising anti-inflammatory effects by targeting neutrophils in vivo, yet such tanshinones, and moreover, their isomeric isotanshinone counterparts, are still a largely underexplored class of compounds, both in terms of synthesis and biological effects. To explore the anti-inflammatory effects of isotanshinones, and the tanshinones more generally, a series of substituted tanshinone and isotanshinone analogues was synthesised, alongside other structurally similar molecules. Evaluation of these using a transgenic zebrafish model of neutrophilic inflammation revealed differential anti-inflammatory profiles in vivo, with a number of compounds exhibiting promising effects. Several compounds reduce initial neutrophil recruitment and/or promote resolution of neutrophilic inflammation, of which two also result in increased apoptosis of human neutrophils. In particular, the methoxy-substituted tanshinone 39 specifically accelerates resolution of inflammation without affecting the recruitment of neutrophils to inflammatory sites, making this a particularly attractive candidate for potential pro-resolution therapeutics, as well as a possible lead for future development of functionalised tanshinones as molecular tools and/or chemical probes. The structurally related β-lapachones promote neutrophil recruitment but do not affect resolution. We also observed notable differences in toxicity profiles between compound classes. Overall, we provide new insights into the in vivo anti-inflammatory activities of several novel tanshinones, isotanshinones, and structurally related compounds.

PRIMIN DERIVATIVES, METHOD OF PREPARATION THEREOF AND USE THEREOF

The present invention provides primin derivatives of general formula II and/or III, wherein R1 is selected from the group consisting of methyl and hydrogen, R2 is selected from the group consisting of methoxy, hydroxy, hydrogen, Rsu

Facile construction of 3-hydroxyphenanthrene-1,4-diones: Key intermediates to tanshinone i and its A-ring-modified analogue

A mild synthetic approach was established allowing for a convenient construction of tricyclic hydroxyphenanthraquinones, the key precursor for total synthesis of tanshinone I. This tandem process includes decarboxylative radical alkylation, intramolecular C-H arylation and one-pot O-demethylation and aromatization. Variously substituted phenylpropanoic acids were well tolerated in this approach, and synthesis of tanshinone I (1) was finally successful in six straight steps in 19% overall yields from commercially available 5-bromovanillin.