210115-30-3

Basic information

• Product Name: 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE
• Synonyms: 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE;3-(3-Bromophenyl)propanal;BENZENEPROPANAL, 3-BROMO-
• CAS NO: 210115-30-3
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.07116
• Mol File: 210115-30-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 267.764°C at 760 mmHg
• Flash Point: 77.314°C
• Appearance: /
• Density: 1.399g/cm³
• Vapor Pressure: 0.008mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE(210115-30-3)
• EPA Substance Registry System: 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE(210115-30-3)

Safety Data

• Hazardous Substances Data: 210115-30-3(Hazardous Substances Data)

Usage

General Description

3-(3-Bromo-phenyl)-propionaldehyde is a chemical compound with the molecular formula C9H9BrO. It is also known by the name "Molecular Structure of 3-(3-Bromo-phenyl)-propionaldehyde." 3-(3-BROMO-PHENYL)-PROPIONALDEHYDE is a pale yellow to light brown liquid with a strong, pungent odor. It is primarily used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also utilized in the production of perfumes and fragrances. Additionally, this chemical may have some potential as a reagent in organic synthesis due to its unique properties and reactivity. However, it is important to handle this compound with caution as it may be harmful if it comes into contact with the skin or is ingested.

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 
• 42287-90-1 3-(3-bromophenyl)propanoic acid 
• 24398-80-9 ethyl 3-bromo-cinnamate 
• 40640-97-9 ethyl 3-(3-bromophenyl)propanoate 

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 
• 210114-93-5 5-(3-{[3-(3-bromo-phenyl)-propyl]-methanesulfonyl-amino}-propyl)-thiophene-2-carboxylic acid tert-butyl ester 
• 210113-16-9 5-(3-{[3-(3-Bromo-phenyl)-propyl]-methanesulfonyl-amino}-propyl)-thiophene-2-carboxylic acid 
• 14473-91-7 3-Bromocinnamic acid 

Relevant articles and documents

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.

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.

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.