13195-79-4

Usage

Uses

Used in Organic Synthesis:
ALPHA,ALPHA,4-TRIBROMOACETOPHENONE is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, including nucleophilic substitution and oxidation, which are crucial for the development of new organic compounds.
Used in Fragrance Industry:
In the fragrance industry, ALPHA,ALPHA,4-TRIBROMOACETOPHENONE is used as a fragrance ingredient due to its strong odor, contributing to the scent profiles of perfumes and other cosmetic products.
Used in Pharmaceutical Industry:
ALPHA,ALPHA,4-TRIBROMOACETOPHENONE is utilized in the pharmaceutical industry for the production of various drugs and medications, highlighting its importance in the development of therapeutic agents.

InChI:InChI=1/C9H9N3O/c1-6-11-8-5-3-2-4-7(8)9(13)12(6)10/h2-5H,10H2,1H3

Upstream product

• 99-90-1 para-bromoacetophenone 
• 67-56-1 methanol 
• 1585-07-5 1-bromo-4-ethylbenzene 
• 59862-55-4 p-bromoacetophenone oxime 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 73387-60-7 1-(4-bromophenyl)-3-(dimethylamino)prop-2-en-1-one 
• 3156-37-4 4-bromo-β-nitrostyrene 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 6940-50-7 4-bromo-DL-mandelic acid 
• 586-76-5 4-Bromobenzoic acid 
• 86435-90-7 (4-bromo-phenyl)-glyoxal dioxime 
• 201206-25-9 2,2-dibromo-1-(4-bromo-phenyl)-ethanone oxime 
• 14917-59-0 p-bromobenzoyl azide 
• 99-90-1 para-bromoacetophenone 
• 99-73-0 para-bromophenacyl bromide 
• 7451-53-8 ethyl N-(4-bromophenyl)carbamate 
• 146692-14-0 3,5-di(p-bromorobenzoyl)-1,2,4-thiadiazole 
• 163430-77-1 3-(4-bromobenzoylformamido)-4-(4-bromophenyl)-1,2,5-thiadiazole 
• 21669-51-2 1-(4-bromo-phenyl)-2,2-di-morpholin-4-yl-ethanone 
• 30430-04-7 3,3'-bis(4-bromophenyl)-2H,2'H-2,2'-bibenzo[b][1,4]thiazine 
• 82100-81-0 2-(3',5'-dimethylpyrazol-1'yl)-4-(p-bromophenyl)thiazole 
• 65943-30-8 5-(4-bromo-phenyl)-[1,2,4]triazin-3-ylamine 

Relevant academic research and scientific papers

CoFe2O4–SiO2–SO3H nanocomposite as a magnetically recoverable catalyst for oxidative bromination of alkynes

A hybrid catalyst has been prepared by incorporating sulfonic acid onto cobalt ferrite magnetic nanoparticles. The catalyst was successfully applied for rapid (20 min) synthesis of α,α-dibromoketones directly from alkynes and NBS. The reaction works well in the presence of 10 wt% of the catalyst at room temperature to produce the desired products in high yield. The catalyst could be recovered using an external magnet and reused without appreciable change in activity.

Tandem oxidation/bromination of ethyl aromatics to α,α- dibromoacetophenones with molecular oxygen under visible light irradiation

The facile synthesis of α,α-dibromoacetophenones from ethyl-substituted aromatics by aerobic photooxidation has been developed. This synthetic method achieves oxidative dibromination of aromatic ethyl groups by using inexpensive and easily handled bromine sources, harmless visible light and molecular oxygen.

Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones

We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.

Electrochemical Oxidative Functionalization of Arylalkynes: Access to α,α-Dibromo Aryl Ketones

A general and effective protocol to synthesize α,α-dibromo aryl ketones has been developed via an electrochemical oxidative method. The reaction proceeds smoothly at room temperature in an undivided cell without the addition of external oxidants. In the reaction process, LiBr acts as both bromine source and supporting electrolyte. This electrooxidation strategy has good substrate applicability and functional group compatibility. Moreover, the reaction could be scaled up efficiently in a continuous flow cell. The target product could undergo further functionalization for the synthesis of some useful heterocyclic compounds. (Figure presented.).

Safe, Scalable, Inexpensive, and Mild Nickel-Catalyzed Migita-Like C?S Cross-Couplings in Recyclable Water

A new approach to C?S couplings is reported that relies on nickel catalysis under mild conditions, enabled by micellar catalysis in recyclable water as the reaction medium. The protocol tolerates a wide range of heteroaromatic halides and thiols, including alkyl and heteroaryl thiols, leading to a variety of thioethers in good isolated yields. The method is scalable, results in low residual metal in the products, and is applicable to syntheses of targets in the pharmaceutical area. The procedure also features an associated low E Factor, suggesting a far more attractive entry than is otherwise currently available, especially those based on unsustainable loadings of Pd catalysts.

Switchable Synthesis of α,α-Dihalomethyl and α,α,α-Trihalomethyl Ketones by Metal-Free Decomposition of Enaminone C=C Double Bond

The novel free radical-based cleavage of the enaminone C=C double bond is realized by using N-halosuccinimides (NXS) in the presence of benzoyl peroxide (BPO) with mild heating, enabling the tunable synthesis of α,α-dihalomethyl ketones and α,α,α-trihalomethyl ketones under different reaction conditions. The formation of these divergent products involving featured C=C double bond cleavage requires no any metal reagent, and represents one more practical example on the synthesis of poly halogenated methyl ketones via the functionalization of carbon?carbon bond. (Figure presented.).

α,α-Dibromoketone precursors in the synthesis of some new thiazole derivatives: Thiazol-2-yl hydrazonobutanoates, thiazol-2-yl pyrazole-4-carboxylates and acids

In the present study, α,α-dibromoacetophenones are used as efficient precursors for the facile synthesis of several new hydrazonothiazoles, ethyl 3-((4-arylthiazol-2-yl)hydrazono)butanoates, which undergo Vilsmeier-Haack cyclization to obtain thiazolylpyrazole esters, ethyl 3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazole-4-carbxylates, basic hydrolysis of which gives the corresponding acids, 3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazole-4-carbxylic acids. All these compounds are tested for antibacterial activity against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis; Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa and antifungal activity against Saccharomyces cerevisiae and Candida albicans.

Selective Debromination of α,α,α-Tribromomethylketones with HBr–H2O Reductive Catalytic System

A debromination of α,α,α-tribromomethylketones is developed for chemoselective synthesis of α-mono- and α,α-dibromomethylketones with high selectivity under H2O–HBr reductive conditions. This method offers an efficient and direct way to synthesize α-mono or α,α-dibromomethylketone compounds in high to excellent yields through the process of HBr self-circulation in water.

Method for preparing alpha,alpha-dihalogenated acetophenone compound

The invention belongs to the technical field of organic synthesis and in particular relates to a method for preparing an alpha,alpha-dihalogenated acetophenone compound. The preparation method provided by the invention comprises the following steps: in an alcohol solvent, enabling nitroalkenes, electrophilic halogen reagents and sodium hydride to react at 55-65 DEG C under a heating condition for5-10 hours, cooling the components to the room temperature, adding a diluted acid solution, and performing continue stirring for 2-5 hours, so as to obtain a target compound, namely alpha,alpha-dihalogenated acetophenone. The method for preparing the alpha,alpha-dihalogenated acetophenone compound, which is provided by the invention, is simple and efficient, mild in condition, easy in raw materialobtaining, green and environment-friendly and simple and convenient to operate, and as a synthesis intermediate, the obtained alpha,alpha-dihalogenated acetophenone compound has the potential of being widely used in fields such as medicine chemical engineering.

Electrochemical Oxidative Oxydihalogenation of Alkynes for the Synthesis of α,α-Dihaloketones

An electrochemical oxydihalogenation of alkynes has been developed for the first time. Using this sustainable protocol, a variety of α,α-dihaloketones can be prepared with readily available CHCl3, CH2Cl2, ClCH2CH2Cl, and CH2Br2 as the halogen source under electrochemical conditions at room temperature.