22539-93-1

Basic information

• Product Name: BENZYLOXYACETONE
• Synonyms: 1-BENZYLOXY-2-PROPANONE;BENZYLOXYACETONE;1-(Benzyloxy)acetone;1-(Benzyloxy)propane-2-one;1-(Benzyloxy)propan-2-one;2-Propanone, 1-(phenylMethoxy)-;Benzyloxyacetone 90%
• CAS NO: 22539-93-1
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• Mol File: 22539-93-1.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 259 °C(lit.)
• Flash Point: >230 °F
• Appearance: Liquid
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0077mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: BENZYLOXYACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYLOXYACETONE(22539-93-1)
• EPA Substance Registry System: BENZYLOXYACETONE(22539-93-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22539-93-1(Hazardous Substances Data)

Usage

Uses

Benzyloxyacetone (1-Benzyloxy-2-propanone) may be used in the synthesis of:7-benzyloxy-6-methyl-5-hepten-1-yne(Z)-2-methylhept-2-en-6-yn-1-o1(S)-(+)-1,2-propanediol, 1-benzyl etherIt may be used as a starting material in synthesizing (2S,4RS)-4-acetoxy-2-[(benzyloxy)methyl]-2-methyldioxolane and (2R,4RS)-4-acetoxy-2-[(benzyloxy)methyl]-2-methyldioxolane.

General Description

Benzyloxyacetone (α-Benzyloxyacetone) is an α-substituted acetone. It undergoes direct aldol reaction with 4-nitrobenzaldehyde in the presence of (S)-BINAM-L-prolinamide/benzoic acid to form predominantly the syn-diasteroisomer.

InChI:InChI=1/C10H12O2/c1-9(11)7-12-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

Upstream product

• 100-51-6 benzyl alcohol 
• 33106-26-2 2-benzyloxypropanol 
• 14593-43-2 benzyl allyl ether 
• 100-39-0 benzyl bromide 
• 4039-82-1 Benzyl propargyl ether 
• 13807-91-5 benzyloxy-2-propanol 
• 67354-34-1 ethyl 4-benzyloxyacetoacetate 
• 104-15-4 toluene-4-sulfonic acid 
• 100-44-7 benzyl chloride 
• 116-09-6 hydroxy-2-propanone 
• 13620-31-0 benzyloxyacetonitrile 
• 75-16-1 methylmagnesium bromide 
• 5658-46-8 ((2-methylallyloxy)methyl)benzene 
• 872-36-6 vinylene carbonate 

Downstream Products

• 132735-41-2 (2S,4R)-2-benzyloxymethyl-2,4-dimethyl-1,3-dioxane 
• 158068-85-0 (Z)-4-Benzyloxy-2-methoxy-3-methyl-but-2-enenitrile 
• 80713-13-9 (Z)-7-benzyloxy-6-methyl-5-hepten-1-yne 
• 130444-90-5 (E)-7-benzyloxy-6-methyl-5-hepten-1-yne 
• 91968-72-8 1-(benzyloxy)-2-methyl-2-propanol 
• 106345-41-9 (+/-)-(2S^*, 3R^*, 4S^*, 5R^*)-1,5-bis(benzyloxy)-2,4-dimethyl-3-((R^*)-phenylsulfinyl)-2-hexanol 
• 106345-41-9 (2R,4S,5S)-3-((R)-Benzenesulfinyl)-1,5-bis-benzyloxy-2,4-dimethyl-hexan-2-ol 
• 13807-91-5 (2S)-1-(benzyloxy)propan-2-ol 
• 89401-28-5 (2R)-1-(benzyloxy)propan-2-ol 
• 198215-76-8 4,5-di-O-benzoyl-2,3-O-((1R*)-1-benzyloxymethylethylidene)-β-D-fructopyranose 
• 198215-77-9 4,5-di-O-benzoyl-2,3-O-((1S*)-1-benzyloxymethylethylidene)-β-D-fructopyranose 
• 176848-20-7 1-benzyloxy-2,2-dimethoxypropane 
• 393536-49-7 (R_S)-N-(2-(1-benzyloxy)propylidene-2-methylpropane)sulfinamide 
• 310887-98-0 4-benzyloxy-3-methylbut-2-enoic acid methyl ester 

Relevant articles and documents

Gold N-Heterocyclic Carbene Catalysts for the Hydrofluorination of Alkynes Using Hydrofluoric Acid: Reaction Scope, Mechanistic Studies and the Tracking of Elusive Intermediates

An efficient and chemoselective methodology deploying gold-N-heterocyclic carbene (NHC) complexes as catalysts in the hydrofluorination of terminal alkynes using aqueous HF has been developed. Mechanistic studies shed light on an in situ generated catalyst, formed by the reaction of Br?nsted basic gold pre-catalysts with HF in water, which exhibits the highest reactivity and chemoselectivity. The catalytic system has a wide alkyl substituted-substrate scope, and stoichiometric as well as catalytic reactions with tailor-designed gold pre-catalysts enable the identification of various gold species involved along the catalytic cycle. Computational studies aid in understanding the chemoselectivity observed through examination of key mechanistic steps for phosphine- and NHC-coordinated gold species bearing the triflate counterion and the elusive key complex bearing a bifluoride counterion.

Tsuji-Wacker Oxidation of Terminal Olefins using a Palladium-Carbon Nanotube Nanohybrid

Palladium nanoparticles supported on carbon nanotubes were used in the Tsuji-Wacker oxidation. The palladium-based nanohybrid was found to be very active in combination with cuprous chloride for the selective oxidation of terminal olefins into methyl ketones. The co-catalytic system operates under very mild and sustainable conditions (room temperature, atmospheric pressure, low catalyst loading), as opposed to previously reported catalysts, and can be recycled without any loss in activity. Give it a whack: Palladium nanoparticles supported on carbon nanotubes are used in combination with cuprous chloride for the selective Tsuji-Wacker oxidation of terminal olefins into methyl ketones. The co-catalytic system operates under very mild and sustainable conditions and can be recycled without any loss in activity.

Iron(III) sulfate as terminal oxidant in the synthesis of methyl ketones via wacker oxidation

An efficient and environmentally benign method using Fe(III) sulfate as a terminal oxidant in the synthesis of methyl ketones from terminal olefins via the Wacker process is developed. The methodology offers high selectivity for a Markonikov product, shows good functional group compatibility, involves mild reaction conditions, and is operationally simple. Fe2(SO 4)3 is the sole terminal oxidant in this process. The method holds potential for future applications in organic synthesis.