31558-41-5

Usage

Uses

4-Bromo-2,5-dimethoxybenzene is used as a pharmaceutical intermediate.

InChI:InChI=1/C9H9BrO3/c1-12-8-4-7(10)9(13-2)3-6(8)5-11/h3-5H,1-2H3

Upstream product

• 93-02-7 2,5-dimethoxybenzaldehyde 
• 72054-76-3 2-(2',5'-dimethoxyphenyl)-1,3-dioxolane 
• 2674-34-2 1,4-dibromo-2,5-dimethoxybenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 4885-02-3 Dichloromethyl methyl ether 
• 25245-34-5 1-bromo-2,5-dimethoxybenzene 
• 1191-17-9 1,1-dichloromethyl-methyl ether 

Downstream Products

• 31558-33-5 1c-<4-Brom-2,5-dimethoxy-phenyl>-2-nitro-propen 
• 98537-45-2 4-bromo-2,5-dimethoxy-β-nitrostyrene 
• 87050-61-1 (4-bromo-2,5-dimethoxy-phenyl)-methanol 
• 105479-97-8 4-(Benzylthio)-2,5-dimethoxybenzaldehyd 
• 35458-39-0 4-bromo-2,5-dimethoxybenzoic acid 
• 98545-68-7 2-bromo-1,4-dimethoxy-5-nitrobenzene 
• 370884-62-1 4-bromo-5-hydroxy-2-methoxybenzaldehyde 
• 557757-32-1 4-bromo-2,5-dimethoxyphenol 
• 681171-33-5 2-(4-boronic acid-2,5-dimethoxy-phenyl)-[1,3]dioxolane 
• 681171-35-7 4-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-yl]-2,5-dimethoxy-benzaldehyde 
• 681171-36-8 {4-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-yl]-2,5-dimethoxy-benzyl}-dimethyl-amine 
• 681171-38-0 (3-{4-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-yl]-2,5-dimethoxy-phenyl}-allyl)-dimethylamine 
• 762275-75-2 2-(2,5-dimethyl-pyrrol-1-yl)-6-(4-[1,3]dioxolan-2-yl-2,5-dimethoxy-phenyl)-pyridine 
• 681171-39-1 (3-{4-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-yl]-2,5-dimethoxy-phenyl}-propyl)-dimethylamine 

Relevant academic research and scientific papers

5-HT2A/5-HT2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism

The toxic hallucinogen 25B-NBOMe is very rapidly degraded by human liver microsomes and has low oral bioavailability. Herein we report on the synthesis, microsomal stability, and 5-HT2A/5-HT2C receptor profile of novel analogues of 25B-NBOMe modified at the primary site of metabolism. Although microsomal stability could be increased while maintaining potent 5-HT2 receptor agonist properties, all analogues had an intrinsic clearance above 1.3 L/kg/h predictive of high first-pass metabolism.

Total synthesis of eryvarin H and its derivatives and their biological activity as ERRγ inverse agonist

Total synthesis of eryvarin H and a biological investigation of its analogues as a potential inverse agonist of ERRγ are described here. Among the 13 analogues prepared by the modular synthetic route, eryvarin H and compound 12 showed meaningful ERRγ inverse agonistic activities along with moderate selectivity over ERα and other nuclear receptors in the cell-based reporter gene assay.

Synthesis of murrayaquinone A and analogues via ring-closing C-H arylation

A compact synthesis of Murrayaquinone A is reported, based on sequential Buchwald-Hartwig amination/annulative C-H activation followed by oxidation of the intermediate carbazole. The methodology can be readily extended to other analogues with electron-rich quinone rings.

Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides

Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl4 and AuCl3 under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl4 was found to be effective and compatible with various functional groups present in the substrates. A mechanism accounting for its catalytic cycle is proposed and discussed.

Storable arylpalladium(II) reagents for alkene labeling in aqueous media

We show that arylpalladium(II) reagents linked to biotin and indocyanine dye residues can be prepared by decarboxylative palladation of appropriately substituted electron-rich benzoic acid derivatives. When prepared under the conditions described, these organometallic intermediates are tolerant of air and water, can be stored for several months in solution in dimethyl sulfoxide, and permit biotin- and indocyanine dye-labeling of functionally complex olefinic substrates in water by Heck-type coupling reactions.

FLUORESCENT PROBES FOR ZINC

A compound represented by the following general formula (I) or a salt thereof: wherein R1 represents hydrogen atom, an alkyl group, an alkoxy group, or hydroxy group; R2 represents a group represented by the following formula (A): wherein X1 to X4 represent hydrogen atom, an alkyl group, or 2-pyridylmethyl group, and m and n represent 0 or 1; Y represents a single bond or -CO-; R3 represents a carboxy-substituted aryl group, a carboxy-substituted heteroaryl group, benzothiazol-2-yl group, or 5-oxo-2-thioxo-4-imidazolyzinylidenmethyl group], and a fluorescent probe for zinc which comprises said compound or a salt thereof.

Total synthesis of atroviridin

A total synthesis of atroviridin (1) based on biosynthetic principles is presented. The tetracyclic xanthone structure of the natural product was constructed by coupling aryl bromide 8 with aldehyde 7 and subsequent intramolecular conjugate addition on a quinone precursor. Bromide 8 was produced from aldehyde 9 via a sequence of steps involving Baeyer-Villiger oxidation and Claisen cyclization.

A novel, cell-permeable, fluorescent probe for ratiometric imaging of zinc ion

Zn2+ plays important roles in various biological systems; as a result, the development of tools that can visualize chelatable Zn2+ has attracted much attention recently. We report here newly synthesized fluorescent sensors for Zn2+, ZnAF-Rs, whose excitation maximum is shifted by Zn2+ under physiological conditions. Thus, these sensors enable ratiometric imaging, which is a technique to reduce artifacts by minimizing the influence ofextraneous factors on the fluorescence of a probe. Ratiometric measurement can provide precise data, and some probes allow quantitative detection. ZnAF-Rs are the first ratiometric fluorescent sensors for Zn2+ that enable quantitative analysis under physiological conditions. ZnAF-Rs also possess suitable Kd for applications, and high selectivity against other biologically relevant cations, especially Ca2+. Using these probes, changes of intracellular Zn2+ concentration in cultured cells were monitored successfully. We believe that these probes will be extremely useful in studies on the biological functions of Zn2+. Copyright

Biomimetic synthesis of (-)-longithorone A

An enantioseletive, biomimetic synthesis of (-)-longithorone A has been achieved using an intermolecular/transannular Diels-Alder sequence which provides some support for the proposed biosynthesis. The cycloaddition precursors were two [12]-paracyclophanes that were constructed with atropisomer control during ene-yne metathesis macrocyclizations. Copyright

Selective preparation of 4-(bromo or iodo)-2,5-dimethoxybenzonitrile and 2-(bromo or iodo)-3,6-dimethoxybenzonitrile from 2,5-dimethoxybenzaldehyde

By use of appropriate reactions and sequence of steps, 2,5- dimethoxybenzaldehyde can be converted either to 4-(bromo or iodo)-2,5- dimethoxybenzonitrile or 2-(bromo or iodo)-3,6-dimethoxybenzonitrile.