13651-12-2

Usage

Chemical Properties

White solid

Upstream product

• 99-91-2 para-chloroacetophenone 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 622-98-0 4-chloro(ethylbenzene) 
• 873-73-4 4-n-chlorophenylacetylene 
• 52119-96-7 2,2,2-tribromo-1-(4-chlorophenyl)ethan-1-one 
• 104-88-1 4-chlorobenzaldehyde 
• 92617-56-6 2,2,2-tribromo-1-(4-chlorophenyl)methanol 
• 28587-05-5 3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one 
• 1073-67-2 4-vinylbenzyl chloride 
• 1956-39-4 4-chloroacetophenone oxime 
• 141-78-6 ethyl acetate 
• 108-90-7 chlorobenzene 

Downstream Products

• 7138-34-3 p-chloromandelic acid 
• 32090-75-8 (4-chloro-phenyl)-hydroxyimino-acetaldehyde oxime 
• 201206-26-0 2,2-dibromo-1-(4-chloro-phenyl)-ethanone oxime 
• 21368-28-5 4-chlorobenzoyl azide 
• 115505-07-2 2-(4-chlorophenyl)ethanonyl ethyl sulfide 
• 146692-13-9 3,5-bis(4-chlorobenzoyl)-1,2,4-thiadiazole 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 163430-76-0 3-(4-chlorobenzoylformamido)-4-(4-chlorophenyl)-1,2,5-thiadiazole 
• 74-11-3 para-chlorobenzoic acid 
• 137063-71-9 3,3'-bis(4-chlorophenyl)-2H,2'H-2,2'-bibenzo[b][1,4]thiazine 
• 82100-78-5 2-(3',5'-dimethyl-pyrazol-1'yl)-4-(p-chlorophenyl)thiazole 
• 1068459-75-5 2-bromo-2-(4-chlorophenyl)pent-4-enal 
• 1081758-21-5 2-(4-chlorophenyl)-3,3-dibromoacrylonitrile 
• 34966-48-8 ethyl 2-(4-chlorophenyl)-2-oxoacetate 

Relevant academic research and scientific papers

Direct synthesis of α-keto esters from ethylbenzenes using 48% aqueous HBr by aerobic visible light photooxidation

We report that ethylbenzenes can be directly oxidized to the corresponding -keto esters with molecular oxygen in the presence of 48% aqueous HBr under visible light irradiation. This synthetic procedure is the first example for direct preparation of the corresponding α-keto esters from ethylbenzenes. Georg Thieme Verlag Stuttgart - New York.

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.).

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.

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.

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.).

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.

Visible-light-promoted oxidative halogenation of alkynes

In nature, halogenation promotes the biological activity of secondary metabolites, especially geminal dihalogenation. Related natural molecules have been studied for decades. In recent years, their diversified vital activities have been explored for treating various diseases, which call for efficient and divergent synthetic strategies to facilitate drug discovery. Here we report a catalyst-free oxidative halogenation achieved under ambient conditions (halide ion, air, water, visible light, room temperature, and normal pressure). Constitutionally, electron transfer between the oxygen and halide ion is shuttled via simple conjugated molecules, in which phenylacetylene works as both reactant and catalyst. Synthetically, it provides a highly compatible late-stage transformation strategy to build up dihaloacetophenones (DHAPs).

Micelle-Enabled Photoassisted Selective Oxyhalogenation of Alkynes in Water under Mild Conditions

Using micelles of FI-750-M, visible light, photocatalysts, and inexpensive halogenating reagents, such as N-bromosuccinimide and N-chlorosuccinimde, selective oxyhalogenations of alkynes were achieved in water under very mild conditions. No halogenation at the aromatic rings was detected, and control experiments revealed the radical pathway. The easily conducted protocol exhibited high reproducibility, was readily adjusted to gram scale, and allowed for recycling of reaction medium and catalyst.