5470-14-4

Usage

Uses

Used in Organic Synthesis:
(6-Bromo-benzo[1,3]dioxol-5-yl)-acetic acid is used as a synthetic intermediate for the preparation of various organic compounds. Its bromine atom allows for further functionalization and modification, making it a versatile building block in the synthesis of complex organic molecules.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (6-Bromo-benzo[1,3]dioxol-5-yl)-acetic acid is utilized for the development of potential pharmaceuticals. Its unique structure and functional groups can be exploited to design and synthesize new drug candidates with therapeutic potential.
Used in Chemical Reactions and Synthetic Processes:
The acetic acid group present in (6-Bromo-benzo[1,3]dioxol-5-yl)-acetic acid imparts some acidic properties to the compound. This makes it useful in certain chemical reactions and synthetic processes where acidic conditions or catalysts are required.

InChI:InChI=1/C9H7BrO4/c10-6-3-8-7(13-4-14-8)1-5(6)2-9(11)12/h1,3H,2,4H2,(H,11,12)

Upstream product

• 5434-50-4 2-(5-bromobenzo[d][1,3]dioxol-6-yl)acetonitrile 
• 956084-13-2 (6-bromo-benzo[1,3]dioxol-5-yl)-pyruvic acid 
• 889115-21-3 2-{5-bromobenzo[d][1,3]dioxol-6-yl}acetaldehyde 
• 5434-47-9 5-bromo-6-bromomethylbenzo[1,3]dioxole 
• 5025-53-6 5-bromo-6-methylbenzo[d][1,3]dioxole 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 64603-67-4 5-bromo-6-(chloromethyl)benzo[d][1,3]dioxole 
• 6642-34-8 6-bromopiperonyl alcohol 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 

Downstream Products

• 130862-09-8 2-(6-bromo-benzo[1,3]dioxol-5-yl)-3t-(2-methoxy-6-nitro-phenyl)-acrylic acid 
• 131410-39-4 2-(6-bromo-benzo[1,3]dioxol-5-yl)-3t-(2-nitro-phenyl)-acrylic acid 
• 51665-84-0 methyl (6-bromobenzo<1,3>dioxol-5-yl)acetate 
• 3862-34-8 flemichapparin C 
• 1983-72-8 medicagol 
• 58446-66-5 2-(5-bromobenzo[1,3]dioxol-6-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide 
• 1592683-38-9 C₂₇H₂₆BrNO₅ 
• 1610775-08-0 C₂₄H₂₀BrNO₃ 
• 1592683-36-7 C₂₄H₂₂BrNO₃ 
• 1592683-34-5 C₂₄H₂₂BrNO₄ 
• 1454883-54-5 7-(benzyloxy)-1-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)-6-methoxyisochroman 

Relevant academic research and scientific papers

Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (?)-akuammicine and (?)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.

Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins

A copper-catalyzed intramolecular cross dehydrogenative C-O coupling reaction of 2′-hydroxyl-3-arylcoumarins was developed. This protocol provided a facile and efficient strategy for the construction of natural coumestans and derivatives in moderate to high yields. This transformation exhibited good functional group compatibility and was amenable to substrates with free phenolic hydroxyl groups.

Oxidation nandina philippine alkali synthetic method and its application

The invention discloses a synthetic method of oxidized nantenine and application of the oxidized nantenine. The synthetic method of the oxidized nantenine comprises the following steps: taking 2-(benzo[d][1,3]dioxol-5-yl)acetic acid and 3,4-dimethoxy phenethylamine as starting materials, and conducting seven-step reaction to synthesize the oxidized nantenine. Compared with the prior art, the organic complete synthetic method of the oxidized nantenine is provided by the invention; experiments indicate that the oxidized nantenine has a proliferation inhibitory activity against a plurality of human tumor cell strains, shows up a good antitumor activity in vitro, is excellent in potential medicinal value, and can be applied to preparation of various anti-tumor drugs.

Rapid synthesis and zebrafish evaluation of a phenanthridine-based small molecule library

A Heck cyclisation approach is described for the rapid synthesis of a library of natural product-like small molecules, based on the phenanthridine core. The synthesis of a range of substituted benzylamine building blocks and their incorporation into the library is reported, together with a highly selective cis-dihydroxylation protocol that enables access to the target compounds in an efficient manner. Biological evaluation of the library using zebrafish phenotyping has led to the discovery of compound 20c, a novel inhibitor of early-stage zebrafish embryo development.

Synthesis of N-alkoxyindol-2-ones by copper-catalyzed intramolecular N-arylation of hydroxamates

The first example of copper-catalyzed intramolecular N-arylation of hydroxamic acid derivatives is presented. Based on this transformation a new method for the synthesis of N-alkoxyindol-2-ones from 2-(2-bromoaryl) acetylhydroxamates has been developed. T

Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity

The molecular design, chemical synthesis, and biological evaluation of two distinct series of platensimycin analogues with varying degrees of complexity are described. The first series of compounds probes the biological importance of the benzoic acid subunit of the molecule, while the second series explores the tetracyclic cage domain. The biological data obtained reveal that, while the substituted benzoic acid domain of platensimycin is a highly conserved structural motif within the active compounds with strict functional group requirements, the cage domain of the molecule can tolerate considerable structural modifications without losing biological action. These findings refine our present understanding of theplatensimycin pharmacophore and establish certain structure-activity re lationships from which the next generation of designed analogues of thisnew antibiotic may emerge.

Convergency and divergency as strategic elements in total synthesis: The total synthesis of (-)-drupacine and the formal total synthesis of (±)-cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine

(Chemical Equation Presented) A concise route toward the syntheses of (-)-drupacine and (+)- and (-)-cephalotaxine has been developed. The syntheses rely on Pd(II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly cons

Synthesis of 8,9-(1,3-benzodioxolo-5,6)-5-azatricyclo[8.2.1.0 1,5]tridec-11-en-6-one. A convenient route to structural analogs of the alkaloid cephalotaxine

A synthetic route to 8,9-(1,3-benzodioxolo-5,6)-5-azatricyclo[8.2.1.0 1,5]tridec-11-en-6-one structurally isomeric to the pentacyclic cephalotaxine nucleus is suggested. The route is based on the sequence including diallylboration of 2-pyrrolidinone and intramolecular meta-thesis of the resulting 2,2-diallylpyrrolidine, giving rise to 1-azaspiro[4.4]non-7-ene. This product was N-acylated with 6-bromohomopiperonylic acid chloride and then subjected to intramolecular cyclization according to the Heck reaction.