13997-74-5

Basic information

• Product Name: phenol, 4-bromo-2-(2-propenyl)-
• Synonyms: 2-allyl-4-bromophenol;phenol, 4-bromo-2-(2-propenyl)-;4-bromo-2-prop-2-enylphenol;4-bromo-2-prop-2-enyl-phenol
• CAS NO: 13997-74-5
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.07116
• Mol File: 13997-74-5.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 273.3°C at 760 mmHg
• Flash Point: 119.1°C
• Appearance: /
• Density: 1.435g/cm³
• Vapor Pressure: 0.00345mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: phenol, 4-bromo-2-(2-propenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: phenol, 4-bromo-2-(2-propenyl)-(13997-74-5)
• EPA Substance Registry System: phenol, 4-bromo-2-(2-propenyl)-(13997-74-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13997-74-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H9BrO/c1-2-3-7-6-8(10)4-5-9(7)11/h2,4-6,11H,1,3H2

Upstream product

• 106-41-2 4-bromo-phenol 
• 107-05-1 3-chloroprop-1-ene 
• 584-08-7 potassium carbonate 
• 106-95-6 allyl bromide 
• 1745-81-9 o-Allylphenol 
• 25244-30-8 4-(allyloxy)bromobenzene 
• 111-90-0 ethoxyethoxyethanol 
• 101-84-8 diphenylether 

Downstream Products

• 1558056-46-4 2-allyl-4-bromophenyl ethyl vinylphosphonate 
• 1558056-36-2 2-allyl-4-bromophenyl ethyl allylphosphonate 
• 1450760-94-7 (S)-2-(5-bromo-2,3-dihydrobenzofuran-2-yl)-1-phenylethanone 
• 1378871-34-1 4-methoxy-3-allyl-1-phenylboronic acid 
• 68592-15-4 methylhonokiol 
• 1214741-32-8 (5-bromo-2-(tert-butyldimethylsilanyloxy)phenyl)acetaldehyde 
• 1214741-42-0 C₅₅H₅₂N₂O₁₁S 

Relevant articles and documents

Aluminium chloride-potassium iodide-acetonitrile system: A mild reagent system for aromatic claisen rearrangement at ambient temperature

Claisen rearrangement is used as the standard methods for the generation of complex organic substance. It is one of the well-known methods for the introduction of carbon-carbon bond. We have developed a protocol using allyl aryl ether as a substrate and AlCl3-KI as a mild reagent system and acetonitrile (CH3CN) is taken as solvent at ambient temperature. The reagent system presented in this current work is found to be appropriate for Claisen rearrangement of several aromatic alcohols with excellent yields.

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.

Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins

A palladium-catalyzed fluoroalkylative cyclization of olefins with readily available Rf-I reagents to afford the corresponding fluoroalkylated 2,3-dihydrobenzofuran and indolin derivatives with moderate to excellent yields is reported. This novel procedure provides an efficient method for the construction of Csp3-CF2 and C-O/N bonds in one step. A wide range of functional groups are tolerated. It is proposed that a radical/SET (single electron transfer) pathway proceeding via the fluoroalkyl radical may be involved in the catalytic cycle.