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

General Description

1,3-Benzodioxol-5-yl(phenyl)methanone, also known as 5-APB, is a chemical compound that belongs to the benzofuran class. It is a derivative of the phenethylamine family and is primarily used for research purposes. 5-APB has been found to act as a serotonin-norepinephrine-dopamine releasing agent, meaning it stimulates the release of these neurotransmitters in the brain. It has also been reported to produce empathogenic effects, similar to those of MDMA, and is often used in scientific studies to explore its potential therapeutic applications. However, it is important to note that 5-APB is not approved for human consumption and can pose serious health risks if ingested.

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 
• 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 
• 108-86-1 bromobenzene 
• 120-57-0 piperonal 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 37952-93-5 N-benzoyl saccharin 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 65-85-0 benzoic acid 

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.

Acyl radicals from α-keto acids using a carbonyl photocatalyst: Photoredox-catalyzed synthesis of ketones

Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridylstabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol is compatible with a wide range of functional groups.