210115-30-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-BROMO-PHENYL)-PROPIONALDEHYDE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs and medicinal compounds, enhancing the therapeutic options available in the healthcare sector.
Used in Agrochemical Industry:
In the agrochemical industry, 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE serves as an intermediate in the production of agrochemicals. Its role in the synthesis of these compounds helps to improve agricultural yields and protect crops from pests and diseases.
Used in Perfume and Fragrance Industry:
3-(3-BROMO-PHENYL)-PROPIONALDEHYDE is utilized in the production of perfumes and fragrances. Its strong, pungent odor makes it a valuable component in creating a wide range of scent profiles for various applications, including personal care products and household items.
Used as a Reagent in Organic Synthesis:
Due to its unique properties and reactivity, 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE may have potential as a reagent in organic synthesis. It can be employed in various chemical reactions to produce a range of organic compounds for different industries, expanding its applications beyond its current uses.
It is important to handle 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE with caution, as it may be harmful if it comes into contact with the skin or is ingested. Proper safety measures should be taken during its production, storage, and use to minimize potential risks.

InChI:InChI=1/C9H9BrO/c10-9-5-1-3-8(7-9)4-2-6-11/h1,3,5-7H,2,4H2

Upstream product

• 201230-82-2 carbon monoxide 
• 2039-86-3 3-bromostyrene 
• 65537-54-4 3-(3-bromophenyl)-propan-1-ol 
• 14473-91-7 3-bromocinnamic acid 
• 14473-91-7 3-Bromocinnamic acid 
• 151583-29-8 methyl 3-(3'-bromophenyl)-propionate 
• 24398-80-9 ethyl 3-bromo-cinnamate 
• 40640-97-9 ethyl 3-(3-bromophenyl)propanoate 
• 42287-90-1 3-(3-bromophenyl)propanoic acid 

Downstream Products

• 161173-98-4 1-bromo-3-(but-3-en-1-yl)benzene 
• 97985-66-5 3-(3-bromophenyl)prop-2-en-1-al 
• 97985-66-5 (E)-3-(3-bromophenyl)acrylaldehyde 
• 210113-16-9 5-(3-{[3-(3-Bromo-phenyl)-propyl]-methanesulfonyl-amino}-propyl)-thiophene-2-carboxylic acid 
• 210114-93-5 5-(3-{[3-(3-bromo-phenyl)-propyl]-methanesulfonyl-amino}-propyl)-thiophene-2-carboxylic acid tert-butyl ester 
• 14473-91-7 3-Bromocinnamic acid 

Relevant academic research and scientific papers

Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis

Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).

Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.

A scaffold replacement approach towards new sirtuin 2 inhibitors

Sirtuins (SIRT1–SIRT7) are an evolutionary conserved family of NAD+-dependent protein deacylases regulating the acylation state of ε-N-lysine residues of proteins thereby controlling key biological processes. Numerous studies have found association of the aberrant enzymatic activity of SIRTs with various diseases like diabetes, cancer and neurodegenerative disorders. Previously, we have shown that substituted 2-alkyl-chroman-4-one/chromone derivatives can serve as selective inhibitors of SIRT2 possessing an antiproliferative effect in two human cancer cell lines. In this study, we have explored the bioisosteric replacement of the chroman-4-one/chromone core structure with different less lipophilic bicyclic scaffolds to overcome problems associated to poor physiochemical properties due to a highly lipophilic substitution pattern required for achieve a good inhibitory effect. Various new derivatives based on the quinolin-4(1H)-one scaffold, bicyclic secondary sulfonamides or saccharins were synthesized and evaluated for their SIRT inhibitory effect. Among the evaluated scaffolds, the benzothiadiazine-1,1-dioxide-based compounds showed the highest SIRT2 inhibitory activity. Molecular modeling studies gave insight into the binding mode of the new scaffold-replacement analogues.

Discovery and SAR of Natural-Product-Inspired RXR Agonists with Heterodimer Selectivity to PPARδ-RXR

A known natural product, magnaldehyde B, was identified as an agonist of retinoid X receptor (RXR) α. Magnaldehyde B was isolated from Magnolia obovata (Magnoliaceae) and synthesized along with more potent analogs for screening of their RXRα agonistic activities. Structural optimization of magnaldehyde B resulted in the development of a candidate molecule that displayed a 440-fold increase in potency. Receptor-ligand docking simulations indicated that this molecule has the highest affinity with the ligand binding domain of RXRα among the analogs synthesized in this study. Furthermore, the selective activation of the peroxisome proliferator-activated receptor (PPAR) δ-RXR heterodimer with a stronger efficacy compared to those of PPARα-RXR and PPARγ-RXR was achieved in luciferase reporter assays using the PPAR response element driven reporter (PPRE-Luc). The PPARδactivity of the molecule was significantly inhibited by the antagonists of both RXR and PPARδ, whereas the activity of GW501516 was not affected by the RXR antagonist. Furthermore, the molecule exhibited a particularly weak PPARδagonistic activity in reporter gene assays using the Gal4 hybrid system. The obtained data therefore suggest that the weak PPARδagonistic activity of the optimized molecule is synergistically enhanced by its own RXR agonistic activity, indicating the potent agonistic activity of the PPARδ-RXR heterodimer.

Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,β-enals

A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,β-enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)-olefin and no over-oxidation of γ-hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)- and (R)-coriolides and d-xylo- and d-arabino-C-20 guggultetrols.

Remote Functionalization of α,β-Unsaturated Carbonyls by Multimetallic Sequential Catalysis

The remote functionalization of α,β-unsaturated carbonyls by an array of multimetallic sequential catalytic systems is described. The reactions are triggered by hydrometalation using [Pd-H] or [Ru-H] isomerization catalysts and driven by the formation of thermodynamically more stable 1,2-vinyl arenes. The Pd-catalyzed deconjugative isomerization was combined with a Cu-catalyzed β-borylation of the transiently generated styrenyl derivatives to deliver a range of products that would not be accessible with the use of a single catalyst. [Pd/Cu] catalytic systems were also identified for the highly enantioselective α-hydroboration and α-hydroamination of the styrenyl intermediates. Difunctionalization simultaneously at the benzylic and homobenzylic positions was achieved by combining the isomerization process with Sharpless asymmetric dihydroxylation (SAD) using [Pd/Os] or [Ru/Os] couples. Starting from a simple α,β-unsaturated ester, an isomerization/dihydroxylation/lactonization sequence gave access to a naturally occurring γ-butyrolactone in good yield, with excellent diastereo- and enantioselectivity.

Synthesis of 2-tetralone derivatives by Bi(OTf)3-catalyzed intramolecular hydroarylation/isomerization of propargyl alcohols

Compared to 1-tetralones, 2-tetralones are expensive, less stable, and difficult to synthesize. A concise Bi-catalyzed method was developed for the synthesis of 2-tetralones from 5-phenylpent-1-yn-3-ol derivatives. Diverse 2-tetralones were obtained in moderate to good yields under mild conditions.

Highly selective hydroformylation of vinylarenes to branched aldehydes by [Rh(cod)Cl]2 entrapped in ionic liquid modified silica sol-gel

A co-entrapped mixture of [Rh(cod)Cl]2 and Na[Ph 2P-3-(C6H4SO3)] within a silica sol-gel matrix modified with ca. 5% of 1-butyl-3-[3-(trimethoxysilyl)propyl] imidazolium chloride catalyzes, in n-heptane, the hydroformylation of a variety of vinylarenes. At 50°C and under 6.9 bar each of H2 and CO the reaction is high-yielding and highly selective. Non-hindered substrates give >95 % of branched aldehydes and only 5% of the linear isomers. The ceramic catalyst is leach-proof and recyclable. It does not lose its high catalytic activity and selectivity for at least four runs. The selectivity depends on the pressure of the gases, the temperature and the solvent. The electronic nature has no influence on the selectivity, but the latter is diminished by steric effects. Upon omission of the sol-gel component, the catalyst deteriorates and practically loses its activity after the first half-life of the reaction. In the absence of the ionic liquid, the catalyst undergoes substantial leaching. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.