6941-70-4

Usage

Uses

Used in Pharmaceutical Research:
6-bromo-1,3-benzodioxol-5-ol is used as a key intermediate in the synthesis of various pharmaceutical compounds for the development of new drugs and medications. Its unique structure and functional groups make it a valuable building block in medicinal chemistry.
Used in Drug Discovery:
Due to its reactivity and biological activity, 6-bromo-1,3-benzodioxol-5-ol is used as a starting material in drug discovery processes. Researchers can modify its structure to create new compounds with potential therapeutic properties, contributing to the advancement of medicine.
Used in Chemical Research:
6-bromo-1,3-benzodioxol-5-ol is also used in chemical research to study the properties and reactions of benzodioxole derivatives. Understanding the behavior of 6-bromo-1,3-benzodioxol-5-ol can lead to the development of new synthetic methods and applications in various fields.

Upstream product

• 533-31-3 Sesamol 

Downstream Products

• 6936-58-9 5-benzoyloxy-6-bromo-benzo[1,3]dioxole 
• 6316-28-5 5-bromo-6-[1]naphthoyloxy-benzo[1,3]dioxole 
• 10022-35-2 1-bromo-2-methoxy-4,5-methylenedioxybenzene 
• 5460-53-7 1-acetoxy-2-bromo-4,5-methylenedioxybenzene 
• 950852-66-1 benzyl [(S)-1-benzyl-2-(6-bromobenzo[1,3]dioxol-5-yloxy)ethyl]amine 
• 673477-44-6 6-(2'-(2'',4''-diacetoxyphenyl)ethynyl)-1-methoxy-3,4-methylenedioxybenzene 
• 2035-15-6 (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan 
• 76240-26-1 (+/-)-3-benzyloxy-8,9-methylenedioxyprerocarpan 
• 628328-75-6 methyl 6-[3-(1-hydroxy-6,7-methylenedioxynaphthyl)]-2,3-dimethoxybenzoate 
• 1612146-87-8 methyl 6-[4-(4-methoxybenzyloxy)-2-(methoxymethoxy)benzyloxy]benzo[d][1,3]dioxole-5-carboxylate 
• 1612146-84-5 methyl 6-[4-methoxy-2-(methoxymethoxy)benzyloxy]benzo[d][1,3]-dioxole-5-carboxylate 
• 1160293-80-0 3-bromo-5,6-methylenedioxy-2-naphthyl p-toluenesulfonate 

Relevant academic research and scientific papers

Synthesis and pharmacological activities of some sesquiterpene quinones and hydroquinones

Synthesis of protected siphonodictyal C was achieved via drim-7-en-11-al. Some sesquiterpene quinones and hydroquinones were tested for their pharmacological activities in assays in search of antiproliferative, cytotoxic, antiphlogistic, antirheumatic and anti-inflammatory drugs. Wiedendiol B is a ten times stronger cyclooxygenase-2 inhibitor than the reference compound indomethacine. Cyclooxygenase-2 inhibitors are drugs with antiphlogistic and antirheumatic activity.

COMPOUNDS AND COMPOSITIONS FOR TREATING CNS DISORDERS

The present disclosure provides compounds and pharmaceutical compositions thereof. Methods of making and using the compounds are also provided. The compounds can be used for the treatment, prevention, diagnosis and/or management of various CNS disorders.

Expedient Pd-Catalyzed α-Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids

The general synthesis of diversely substituted dibenzoxepinones by a combined Pd-catalyzed α-arylation and SNAr strategy is reported and applied to the synthesis of Manske's ketone, a key intermediate en route to the total synthesis of cularine alkaloids. In the course of this work, an unanticipated ring contraction reaction to a xanthone was observed and serves as a caveat for the conditions of the widely used α-arylation reaction.

Direct synthesis of 2-substituted benzonitriles: Via alkylcyanation of arynes with N, N -disubstituted aminomalononitriles

An efficient alkylcyanation of in situ generated arynes by N,N-disubstituted aminomalononitriles is described, enabling the direct synthesis of 2-substituted benzonitriles.

A Three-Phase Four-Component Coupling Reaction: Selective Synthesis of o-Chloro Benzoates by KCl, Arynes, CO2, and Chloroalkanes

A transition-metal-free three-phase four-component coupling reaction (3P-4CR) involving KCl, arynes, chloroalkanes and CO2 has been reported for the first time, enabling the incorporation of both chloro and CO2 into an aryne simultaneously. The reactions for the synthesis of different types of o-chloro benzoates can be selectively modulated by the chloroalkane utilized. The corresponding products can be alternatively transformed for postsynthetic functionalizations conveniently.

Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent

Fluorine is probably another favorite hetero-atom for incorporation into small molecules after nitrogen. Among many fluorine-containing groups, trifluoromethyl aryl ethers (ArOCF3) have unique properties in drug design and are difficult to be synthesized, and many different methods were developed to prepare them. A novel one-pot synthesis of o-iodine-aryl trifluoromethyl ethers (ArOCF3I) was described by the reaction of trifluoromethoxylation and iodination with trifluoromethyl aryl sulfonates (TFMS) in this manuscript. The reaction conditions were optimized by screening different solvents, crown ethers, substrates and the ratios and the yields of products were in moderate to high yields (up to 86%).

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

Tandem nucleophilic addition-cycloaddition of arynes with α-iminoesters: Two concurrent pathways to imidazolidines

The tandem nucleophilic addition-cycloaddition reaction has been developed for the synthesis of functionalized imidazolidine derivatives. A variety of α-iminoesters and aryne precursors were well tolerated under the mild reaction conditions. This asymmetric cycloaddition afforded imidazolidine derivatives with high yields, complete regioselectivities, and excellent diastereo- and enantioselectivities. Aryne-induced ylides working as 1,3-dipoles for asymmetric cycloaddition are the notable feature of the present reaction. In the tandem reaction, the [3+2] cycloaddition of aryne-induced ylides with metallized α-iminoesters and metal-catalyzed [3+2] cycloaddition of azomethine ylide with α-iminoesters are two concurrent pathways to imidazolidines.

Copper-Mediated Cascade C-H/N-H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids

An efficient and environmentally benign Cu-mediated method was developed for direct cascade C-H/N-H annulation to construct polyheterocyclic indoloquinoline scaffolds. This method highlights an emerging strategy for transforming inert C-H bonds into versatile functional groups in organic synthesis and provides a new versatile approach for the efficient synthesis of indolo[3,2-c] and [2,3-c]quinoline alkaloids.

Synthesis of o-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides

The aryne insertion into "S-O" bond has been validated recently. This technology is elusively applied to the synthesis of thioethers. In contrast to the reported cases, the reaction described furnished o-aryloxy triarylsulfonium salts, in lieu of thioethe