99233-20-2

Usage

Uses

Used in Pharmaceutical Industry:
α-Hydroxy-2-bromoacetophenone serves as a key building block in the synthesis of various pharmaceuticals. Its hydroxy group facilitates hydrogen bonding interactions, which can be crucial for the compound's biological activity and efficacy in medicinal applications.
Used in Agrochemical Industry:
In agrochemicals, α-hydroxy-2-bromoacetophenone is utilized for the preparation of compounds that can have pesticidal or herbicidal properties, contributing to the development of effective crop protection agents.
Used in Fine Chemicals Industry:
α-hydroxy-2-bromoacetophenone is also employed in the fine chemicals industry, where it is used to produce specialty chemicals with specific applications, such as fragrances, dyes, or other high-value products.
Used in Organic Synthesis:
α-Hydroxy-2-bromoacetophenone is a versatile intermediate in organic synthesis, participating in a variety of reactions that allow for the creation of complex organic molecules with diverse applications across different industries.
Used in Drug Development:
Its potential in drug development is highlighted by its ability to be a part of the synthesis process for biologically active compounds, making it a valuable component in the discovery and creation of new medications.

Upstream product

• 2142-69-0 2-bromophenyl methyl ketone 
• 50-00-0 formaldehyd 
• 6630-33-7 ortho-bromobenzaldehyde 
• 298-12-4 Glyoxilic acid 
• 49851-55-0 2,2'-dibromoacetophenone 
• 67-56-1 methanol 
• 113641-96-6 o-bromoacetophenone trimethylsilyl enol ether 
• 102540-16-9 α-acetoxy-2-bromoacetophenone 
• 583-55-1 1-Bromo-2-iodobenzene 

Downstream Products

• 64132-13-4 3-(hydroxymethyl)-1H-indazole 
• 4498-67-3 1H-Indazole-3-carboxylic acid 
• 920019-58-5 (1-(2,4-dichlorobenzyl)-1H-indazol-3-yl)methanol 
• 252025-49-3 1-(2,4-dichlorobenzyl)-1H-indazole-3-carbaldehyde 
• 50264-69-2 lonidamine 

Relevant academic research and scientific papers

One-Pot Enzymatic-Chemical Cascade Route for Synthesizing Aromatic α-Hydroxy Ketones

2-Hydroxyacetophenone (2-HAP) is an important building block for the production of a series of natural products and pharmaceuticals; however, there is no safe, efficient, and economical method for 2-HAP synthesis. Here, a one-pot enzymatic-chemical cascade route was designed for synthesizing 2-HAP based on retrosynthetic analysis. First, a spontaneous proton-transfer reaction was designed using a computational simulation that enabled 2-HAP synthesis from the isomer 2-hydroxy-2-phenylacetaldehyde. A route for 2-hydroxy-2-phenylacetaldehyde synthesis was then constructed by introducing the unnatural substrate glyoxylic acid into a C-C ligation reaction catalyzed by Candida tropicalis pyruvate decarboxylase. Assembly and optimization of this enzymatic-chemical cascade route resulted in a final yield of 92.7%. Furthermore, stereospecific carbonyl reductases were introduced to construct a synthetic application platform that enabled further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method of cascading spontaneous chemical and enzymatic reactions to synthesize chemicals offers insight into avenues for synthesizing other valuable chemicals.

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

Spiro[indene-1,4′-oxa-zolidinones] Synthesis via Rh(III)-Catalyzed Coupling of 4-Phenyl-1,3-oxazol-2(3 H)-ones with Alkynes: A Redox-Neutral Approach

Transition-metal-catalyzed C-H activation synthesis of heterocyclic spiro[4,4]nonanes has persistently witnessed the use of additional stoichiometric transition-metal oxidant when employing C=C bond as the spiro ring closure site. Herein, we have addressed the issue by reporting a redox-neutral strategy for spiro[indene-1,4′-oxa-zolidinones] synthesis via Rh(III)-catalyzed coupling of 4-phenyl-1,3-oxazol-2(3H)-ones with alkynes. The synthesis features a broad substrate scope and high regiospecificity.

Enantioselective Silver-Catalyzed Cascade Synthesis of Fused Lactone and Lactam Oxazolines

A new and highly stereoselective cascade reaction between isocyanoacetate esters and α-hydroxy and α-amino ketones has been developed. A cinchona alkaloid derived aminophosphine/silver(I) catalyst complex promoted the reaction and enabled the ready synthesis of fused bicyclic γ-lactone and γ-lactam oxazolines with high enantiocontrol (up to 99% ee).

Palladium-Catalyzed (Z)-Selective Allylation of Nitroalkanes: Access to Highly Functionalized Homoallylic Scaffolds

Nitroalkanes undergo decarboxylative allylation in the presence of vinyl-substituted cyclic carbonates, providing a wide variety of functionalized homoallylated compounds with exquisite stereocontrol. This Pd-mediated procedure features operational simplicity, versatile substrate combinations, and also allows for the sequential introduction of different allyl groups in the nitroalkane scaffolds with high levels of stereocontrol through the intermediacy of a (Z)-configured palladacyclic intermediate. As far as we know, the developed protocol is the first general Pd-mediated methodology toward (Z)-configured homoallylic nitroalkanes with attractive functional group diversity.

Preparation method of indazole and application of indazole in medicine synthesis

The invention belongs to the field of chemicals, and relates to a preparation method of indazole and an application of the indazole in medicine synthesis. The invention discloses a preparation method of indazole and an application of the indazole in synthesizing 1H-indazole-3-carboxylic acid, lonidamine, a compound 8, a compound 9, a compound 10, axitinib, YD-3, YC-1 and similar substances thereof.

Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones

Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.

Copper-Mediated SN2′ Allyl-Alkyl and Allyl-Boryl Couplings of Vinyl Cyclic Carbonates

A method for the copper-catalyzed borylmethylation and borylation of vinyl cyclic carbonates through an SN2′ mechanism is reported. These singular reactions involve selective SN2′ allylic substitutions with concomitant ring opening of the cyclic carbonate and with extrusion of CO2 and formation of a useful hydroxyl functionality in a single step. The stereoselectivity of the homoallylic borylation and allylic borylation processes can be controlled, and synthetically useful unsaturated (E)-pent-2-ene-1,5-diols and (E)-but-2-ene-1,4-diols are accessed.

Green organocatalytic α-hydroxylation of ketones

An efficient and green method for the α-hydroxylation of substituted ketones has been developed. This method includes the in situ conversion of various ketones into the corresponding silyl enol ethers and their oxidation to the corresponding α-hydroxy ketones. Two protocols have been established leading either to protected α-hydroxy carbonyls or free α-hydroxy ketones. Both procedures are easy to follow and lead to good to high yields for a variety of ketones.

Copper(I) Oxide-Mediated Cyclization of o-Haloaryl N-Tosylhydrazones: Efficient Synthesis of Indazoles

An efficient synthesis of indazoles from readily accessible E/Z mixtures of o-haloaryl N-tosylhydrazones has been developed. The thermo-induced isomerization of N-tosylhydrazones is discussed. A series of valuable indazole derivatives are prepared in good yields, and the method has been successfully applied to the synthesis of the bioactive compounds, lonidamine, AF-2785, axitinib, YC-1 and YD-3.