4209-24-9

Usage

Synthesis Reference(s)

Synthetic Communications, 20, p. 1625, 1990 DOI: 10.1080/00397919008053082

Upstream product

• 541-88-8 Chloroacetic anhydride 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 73805-23-9 α-chloro-p-methylstyrene oxide 
• 75-05-8 acetonitrile 
• 17263-64-8 2-diazo-1-(4-methylphenyl)ethanone 
• 96222-32-1 2-bromo-2-chloro-1-(p-tolyl)ethan-1-one 
• 4079-54-3 2-hydroxy-1-p-tolyl-ethanone 
• 122-00-9 para-methylacetophenone 
• 33491-04-2 1-(chloroethynyl)-4-methylbenzene 
• 832737-81-2 2-chloro-1,3-bis(4′-methyl-phenyl)-1,3-propanedione 
• 766-97-2 4-n-methylphenylacetylene 
• 40805-62-7 2-iodo-1-(4-methylphenyl)ethanone 
• 67-56-1 methanol 

Downstream Products

• 66047-73-2 2-methyl-4-(4′-methylphenyl)thiazole 
• 65908-21-6 4-(4′-methylphenyl)-2-phenylimidazole 
• 41940-83-4 2-(2-benzoylimino-5-phenyl-[1,3,4]selenadiazol-3-yl)-1-p-tolyl-ethanone 
• 4872-74-6 acetic acid N'-(4-p-tolyl-thiazol-2-yl)-hydrazide 
• 66502-12-3 2-Propylsulfanyl-1-p-tolyl-ethanone 
• 109219-26-3 propan-2-one (4-p-tolyl-selenazol-2-yl)-hydrazone 
• 4871-21-0 4-nitro-benzaldehyde (4-p-tolyl-thiazol-2-yl)-hydrazone 
• 4871-20-9 1-benzylidene-2-(4-p-tolylthiazol-2-yl)hydrazine 
• 66121-83-3 4-(4-p-tolylthiazol-2-ylamino)benzenesulfonamide 
• 62625-57-4 2-phenyl-5-p-tolyl-6H-[1,3,4]thiadiazine 
• 15995-34-3 3-allyl-4-p-tolyl-3H-thiazol-2-one bis-(2-chloro-ethyl)-hydrazone 
• 62625-64-3 2-benzyl-5-p-tolyl-6H-[1,3,4]thiadiazine 
• 15995-33-2 3-phenyl-4-p-tolyl-3H-thiazol-2-one bis-(2-chloro-ethyl)-hydrazone 
• 19765-46-9 2-phenylamino-4-(4-tolyl)-1,3-selenazole 

Relevant academic research and scientific papers

Novel N-hydroxybenzamide-based HDAC inhibitors with branched CAP group

Ongoing effort to gather further knowledge about the structural requirements on histone deacetylase inhibitors led to the synthesis of novel N-hydroxybenzamide-based HDAC inhibitors 1a-o, introducing branched hydrophobic groups at the capping group, and t

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.

Tris-(2-pyridylmethyl)amine-ligated Cu(II) 1,3-diketonate complexes: Anaerobic retro-Claisen and dehalogenation reactivity of 2-chloro-1,3-diketonate derivatives

We report synthetic, structural and reactivity investigations of tris-(2-pyridylmethyl)amine (TPA)-ligated Cu(ii) 1,3-diketonate complexes. These complexes exhibit anaerobic retro-Claisen type C-C bond cleavage reactivity which exceeds that found in analo

Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source

An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.

The Mn-catalyzed paired electrochemical facile oxychlorination of styrenes: Via the oxygen reduction reaction

Reported herein is the electrochemical engendering of chlorine radicals by a manganese catalyst with a controllable pattern, and inexpensive MgCl2 as the chlorine source. In combination with the oxygen reduction reaction, chloroacetophenones were synthesized with abundant styrene as the feedstock in good to excellent yields.

CV-driven Optimization: Cobalt-Catalyzed Electrochemical Expedient Oxychlorination of Alkenes via ORR

Instead of screening reaction conditions by yield-based chemical trial-and-error, potential-based cyclic voltammetry was alternatively employed for optimization of electrochemical oxychlorination of alkenes. With this unconventional screening method, the catalyst system including catalysts, molar ratio of chloride sources and solvents were identified in a rational, time- and energy-efficient manner. The optimal catalytic system in combination with oxygen reduction reaction enabled broad substrate scopes for the desired transformation by taking advantages of persistent radical effect. UV-vis and CV titration experiments confirmed the in-situ formed catalytic species [CoCl5]. Moreover, cyclic voltammetry was applied to obtain mechanistic insights in our reaction system. (Figure presented.).

Iodine-DMSO-promoted divergent reactivities of arylacetylenes

An unprecedented set of efficient, economical, atom-economic and exceedingly selective I2-DMSO-promoted methods is described for the generation of different structures. The reaction represents the first of its kind, involving the use of different iodine concentrations, temperatures, acids and salt to adjust the selectivity for the synthesis of different alkenes, α-functionalized ketones and α-ketomethylthioesters.

Production method of 2-aminophenylacetophenone hydrochloride

The invention discloses a production method of 2-aminophenylacetophenone hydrochloride. The production method includes the steps of 1), production of 2-chlorinated p-methylacetophenone toluene; 2),production of 2-chlorinated p-methylacetophenone hexamethy

Novel carbazole-triazole conjugates as DNA-targeting membrane active potentiators against clinical isolated fungi

A series of carbazole-triazole conjugates were designed, synthesized and characterized by IR, NMR, and HRMS spectra. Biological assay showed that most of the synthesized compounds exhibited moderate and even strong antifungal activities, especially 3,6-dibromocarbazolyl triazole 5d displayed excellent inhibitory efficacy against most of the tested fungal strains (MIC = 2–32 μg/mL) and effectively fungicidal ability towards C. albicans, C. tropicals and C. parapsilosis ATCC 22019 (MFC = 4–8 μg/mL). Its combination use with fluconazole could enhance the antifungal efficacy, and compound 5d also did not obviously trigger the development of resistance in C. albicans even after 10 passages. Preliminary mechanism study revealed that the active molecule 5d could depolarize fungal membrane potential and intercalate into DNA to possibly block DNA replication, thus possibly exhibiting its powerful antifungal abilities. Conjugate 5d could interact with HSA, which was constructive for the further design, modification and screening of drug molecules. Docking investigation demonstrated a non-covalent binding of 5d with CYP51 through hydrogen bond and hydrophobicity. These results strongly suggested that compound 5d could act as a potential template for the development of promising antifungal drugs.

Mild Homologation of Esters through Continuous Flow Chloroacetate Claisen Reactions

The selective chloromethylenation of functionalized esters using chloroacetic acid (CA) and LiHMDS (HMDS=hexamethyldisilazide) in a continuous-flow setup is reported. This Claisen homologation is for the first time extended to bis-chloromethylenation using dichloroacetic acid (DCA), thus giving access to under-explored α,α′-bis-chloroketones. The use of flow conditions enables efficient generation and reaction of the unstable chloroacetate dianion intermediates, leading to unprecedented mild and scalable reaction conditions at an economical reagent stoichiometry (?10 °C, 1 min, 1.0–2.4 equiv dianion). The clean reaction profiles allow subsequent use of the unpurified crude products, which is demonstrated in the synthesis of various heterocycles of broad interest. Furthermore, we report a novel, catalyst-free substitution of the obtained monochloro ketone products with (hetero)aryl zinc enolates to give valuable 1,4-diketones.