86358-27-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(1,3-benzodioxol-5-yl)-2-phenylethane-1,2-dione is used as a synthetic intermediate for the production of various psychoactive substances, such as MDMA (3,4-methylenedioxymethamphetamine) and MDP2P (3,4-methylenedioxyphenyl-2-propanone). Its role in the creation of these substances makes it a crucial component in the pharmaceutical industry, particularly in the development and manufacturing of recreational drugs.
Used in Law Enforcement and Regulatory Agencies:
Due to its potential for abuse and involvement in the illicit drug trade, 1-(1,3-benzodioxol-5-yl)-2-phenylethane-1,2-dione is also used as a target for monitoring and control by law enforcement and regulatory agencies. These agencies are responsible for ensuring that the sale, distribution, and use of 1-(1,3-benzodioxol-5-yl)-2-phenylethane-1,2-dione are in compliance with legal regulations, in order to prevent its misuse and reduce the prevalence of recreational drug abuse.

Upstream product

• 36715-46-5 2-(benzo[d][1,3]dioxol-5-yl)-2-hydroxy-2-phenylethanone 
• 100461-31-2 5-(α,β-dibromo-phenethyl)-benzo[1,3]dioxole 
• 644-34-8 3,4-methylenedioxychalcone 
• 126266-77-1 3,5-methylenedioxy-α-phenylacetophenone 
• 1589-82-8 phenylmagnesium bromide 
• 74156-40-4 1-piperonyl-2-phenylethanol 
• 4439-02-5 3,4-methylenedioxyphenylacetonitrile 
• 40804-81-7 2-(benzo[d][1,3]dioxol-5-yl)-1-phenylethan-1-one 
• 957768-42-2 (3,4-methylenedioxy-phenyl)phenylacetylene 
• 1204518-45-5 C₂₁H₁₅B₃O₉ 
• 63571-96-0 S-ethyl 2-oxo-2-phenylethanethioate 
• 26036-40-8 1-(benzo[d][1,3]dioxol-5-yl)-3-phenylpropane-1,3-dione 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 100-52-7 benzaldehyde 

Downstream Products

• 128622-18-4 benzo[1,3]dioxol-5-yl-hydroxy-phenyl-acetic acid 

Relevant academic research and scientific papers

Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils

The conversion of 1,3-diaryl-2-diazo-1,3-diketones to 1,2-daryl-1,2-diketones (benzils) is reported based on a rhodium(II)-catalyzed aerobic decomposition process. The reaction occurs at ambient temperatures and can be catalyzed by a few dirhodium carboxylates (5 mol %) under a balloon pressure of oxygen. Moreover, an oxygen atom from the O2 reagent is shown to be incorporated into the product, and this is accompanied by the extrusion of a carbonyl unit from the starting materials. Mechanistically, it is proposed that the decomposition may proceed via the interaction of a ketene intermediate resulting from a Wolff rearrangement of the carbenoid, with a rhodium peroxide or peroxy radical species generated upon the activation of molecular oxygen. The proposed mechanism has been supported by the results from a set of controlled experiments. By using this newly developed strategy, a large array of benzil derivatives as well as 9,10-phenanthrenequinone were synthesized from the corresponding diazo substrates in varying yields. On the other hand, the method did not allow the generation of benzocyclobutene-1,2-dione from 2-diazo-1,3-indandione because of the difficulty of inducing the initial rearrangement.

1,2-dicarbonyl compound and synthesis method thereof

The invention discloses a method for synthesizing a 1,2-dicarbonyl compound (1,2-dicarbonylamide or alpha-diketone compound), wherein 1,2-dicarbonyl thioester compounds used as 1,2-dicarbonyl reagentsreact with amine compounds or boric anhydride compounds under appropriate conditions to respectively synthesize a series of 1,2-dicarbonyl compounds. According to the present invention, the 1,2-dicarbonyl compound is obtained by using the stable 1,2-dicarbonyl thioester compound as the dicarbonylation reagent through one-step construction under mild conditions, such that the disadvantage that thetraditional method uses the unstable alpha-carbonyl acyl chloride to synthesize the 1,2-dicarbonyl compound is avoided.

Substituent Effect in the Synthesis of α,α-Dibromoketones, 1,2-Dibromalkenes, and 1,2-Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid

Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α-dibromoketone and 1,2-diketone derivatives. Diarylalkynes with activating groups provided 1,2-diketone derivatives as the major products, whereas diarylalkynes with a non-activating group or alkylarylalkynes gave α,α-dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2-dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations. (Figure presented.).

Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles

An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.

An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: A new facet to classical DMSO oxidation

A conceptually new dimethyl sulfoxide (DMSO) based oxidation process without the use of any activator has been demonstrated for the oxidation of active methylenes and benzhydrols. The developed protocol utilizes the electrophilic center of DMSO for oxidation, which was unexplored before. Mechanistic investigation has confirmed that the source of oxygen is DMSO.

Copper-mediated aerobic oxidative cleavage of α,β-unsaturated ketones to 1,2-diketones

The copper-mediated aerobic oxidative cleavage of α,β- unsaturated ketones to synthesize 1,2-diketones by using potassium acetate as a catalyst and sodium iodide as a promoter in acetic acid is described. The protocol has the advantages of using inexpensive and non-toxic raw materials, high yield and simple work-up procedure. the Partner Organisations 2014.

Oxidation of 1,2,5-Thiadiazolidine 1,1-Dioxides: Synthesis of Diaryl 1,2-Diketones

Treatment of 3,4-diaryl 1,2,5-thiadiazolidine 1,1-dioxides with selenium dioxide followed by hydrolysis of the crude oxidation product furnishes the corresponding diaryl 1,2-diketones. Symmetrical and unsymmetrical diketones are readily prepared by this method.

Synthesis of unsymmetrically substituted benzils via the Friedel-Crafts reaction of arenes with α-chloro-α-(methylthio)acetophenones

Lewis acid-promoted reactions of arenes with α-chloro-α-(methylthio)acetophenones gave the Friedel-Crafts reaction products, which were then treated with 3 molar eq of cupric chloride in aqueous acetone to afford the unsymmetrically substituted benzils.

TELLURIUM DIOXIDE OXIDATION OF STILBENE DIBROMIDES TO BENZILS

Tellurium dioxide reacts with stilbene dibromides in hot acetic acid to give benzils in good to moderate yields.