54225-86-4

Basic information

• Product Name: 1,3-BENZODIOXOL-5-YL(PHENYL)METHANONE
• Synonyms: 1,3-BENZODIOXOL-5-YL(PHENYL)METHANONE;UKRORGSYN-BB BBV-5118601;methanone, 1,3-benzodioxol-5-ylphenyl-;1,3-benzodioxol-5-yl(phenyl)methanone(SALTDATA: FREE)
• CAS NO: 54225-86-4
• Molecular Formula: C₁₄H₁₀O₃
• Molecular Weight: 226.23
• Mol File: 54225-86-4.mol
• Article Data: 40

Chemical Properties

• Melting Point: 56 °C
• Boiling Point: 377.7°C at 760 mmHg
• Flash Point: 173.7°C
• Appearance: /
• Density: 1.265g/cm³
• Vapor Pressure: 6.63E-06mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,3-BENZODIOXOL-5-YL(PHENYL)METHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BENZODIOXOL-5-YL(PHENYL)METHANONE(54225-86-4)
• EPA Substance Registry System: 1,3-BENZODIOXOL-5-YL(PHENYL)METHANONE(54225-86-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 54225-86-4(Hazardous Substances Data)

Usage

Description

1,3-Benzodioxol-5-yl(phenyl)methanone, commonly known as 5-APB, is a chemical compound belonging to the benzofuran class. It is a phenethylamine derivative primarily utilized for research purposes. 5-APB functions as a serotonin-norepinephrine-dopamine releasing agent, stimulating the release of these neurotransmitters in the brain. 1,3-BENZODIOXOL-5-YL(PHENYL)METHANONE has been reported to produce empathogenic effects, akin to those of MDMA, and is frequently employed in scientific studies to investigate its potential therapeutic applications.

Uses

Used in Pharmaceutical Research:
1,3-Benzodioxol-5-yl(phenyl)methanone is used as a research chemical for exploring its potential therapeutic applications. Its ability to stimulate the release of neurotransmitters such as serotonin, norepinephrine, and dopamine makes it a valuable compound for studying the effects of these neurotransmitters on various conditions.
Used in Neurotransmitter Release Studies:
In the field of neuroscience, 1,3-Benzodioxol-5-yl(phenyl)methanone is used as a research tool to investigate the mechanisms of neurotransmitter release. Its action as a releasing agent for serotonin, norepinephrine, and dopamine allows researchers to better understand the role of these neurotransmitters in brain function and behavior.
Used in Empathogenic Effect Research:
1,3-Benzodioxol-5-yl(phenyl)methanone is used in studies focused on empathogenic effects, similar to those produced by MDMA. This research aims to understand the underlying mechanisms of these effects and explore the potential therapeutic uses of 5-APB in treating conditions that may benefit from enhanced empathy and emotional connection.
Used in Drug Development:
Although not yet approved for medical use, 1,3-Benzodioxol-5-yl(phenyl)methanone is used in the development of new drugs targeting neurotransmitter systems. Its unique properties and effects on serotonin, norepinephrine, and dopamine release make it a promising candidate for the development of novel therapeutic agents for various neurological and psychiatric disorders.

InChI:InChI=1/C14H10O3/c15-14(10-4-2-1-3-5-10)11-6-7-12-13(8-11)17-9-16-12/h1-8H,9H2

Upstream product

• 857550-36-8 benzo[d][1,3]dioxol-5-yl(phenyl)methanimine 
• 4382-91-6 1,3-benzodioxol-5-yl(phenyl)methanol 
• 274-09-9 Methylenedioxybenzene 
• 98-88-4 benzoyl chloride 
• 201230-82-2 carbon monoxide 
• 934-56-5 trimethyl(phenyl)stannane 
• 109586-40-5 1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate 
• 860747-27-9 2-(benzo[d][1,3]dioxol-5-yl)-2-phenylacetaldehyde 
• 186581-53-3 diazomethane 
• 13737-36-5 4-bromophenylacetic acid 
• 74-88-4 methyl iodide 
• 108-86-1 bromobenzene 
• 120-57-0 piperonal 
• 4421-09-4 piperonylonitrile 

Downstream Products

• 1387566-44-0 2-(benzo[d][1,3]dioxol-5-yl)-9-hydroxy-2-phenyl-4H-naphtho[2,3-d][1,3]dioxin-4-one 

Relevant articles and documents

Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water

Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C-H bond oxidation functionalization does not require other oxidants and hydrogen accep

Suzuki-Miyaura cross-coupling of esters by selective O-C(O) cleavage mediated by air- And moisture-stable [Pd(NHC)(μ-Cl)Cl]2precatalysts: Catalyst evaluation and mechanism

The cross-coupling of aryl esters has emerged as a powerful platform for the functionalization of otherwise inert acyl C-O bonds in chemical synthesis and catalysis. Herein, we report a combined experimental and computational study on the acyl Suzuki-Miyaura cross-coupling of aryl esters mediated by well-defined, air- and moisture-stable Pd(ii)-NHC precatalysts [Pd(NHC)(μ-Cl)Cl]2. We present a comprehensive evaluation of [Pd(NHC)(μ-Cl)Cl]2 precatalysts and compare them with the present state-of-the-art [(Pd(NHC)allyl] precatalysts bearing allyl-type throw-away ligands. Most importantly, the study reveals [Pd(NHC)(μ-Cl)Cl]2 as the most reactive precatalysts discovered to date in this reactivity manifold. The unique synthetic utility of this unconventional O-C(O) cross-coupling is highlighted in the late-stage functionalization of pharmaceuticals and sequential chemoselective cross-coupling, providing access to valuable ketone products by a catalytic mechanism involving Pd insertion into the aryl ester bond. Furthermore, we present a comprehensive study of the catalytic cycle by DFT methods. Considering the clear advantages of [Pd(NHC)(μ-Cl)Cl]2 precatalysts on several levels, including facile one-pot synthesis, superior atom-economic profile to all other Pd(ii)-NHC catalysts, and versatile reactivity, these should be considered as the 'first-choice' catalysts for all routine applications in ester O-C(O) bond activation.

Selective Acylation of Aryl- A nd Heteroarylmagnesium Reagents with Esters in Continuous Flow

A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/or Grignard was crucial for the reaction outcome. This was leveraged by the obtention of several bisaryl ketones using 2-hydroxy ester derivatives as substrates.