29681-98-9

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-CHLORO-PHENYL)-BUTANE-1,3-DIONE is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its reactivity and the presence of the chloro-phenyl group, which can be further modified in chemical reactions.
Used in Dye Industry:
In the dye industry, 1-(4-CHLORO-PHENYL)-BUTANE-1,3-DIONE is utilized as a starting material for the production of dyes, taking advantage of its chemical properties to create a range of colorants for different applications.
Safety and Storage:
1-(4-CHLORO-PHENYL)-BUTANE-1,3-DIONE should be stored in a cool, dry place to maintain its stability and prevent degradation. Additionally, it is important to handle 1-(4-CHLORO-PHENYL)-BUTANE-1,3-DIONE with care, as it has the potential to cause skin and eye irritation. Proper protective measures, such as wearing gloves and safety goggles, are recommended during its use and storage.

InChI:InChI=1/C10H9FO2/c1-7(12)6-10(13)8-2-4-9(11)5-3-8/h2-5H,6H2,1H3

Upstream product

• 658-13-9 p-fluorobenzoyl cyanide 
• 67-64-1 acetone 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 68415-10-1 1-cyano-(4-fluorophenyl)-1-morpholinomethane 
• 405065-66-9 4-para-fluorophenyl-3-butyn-2-one 
• 352-34-1 4-fluoro-1-iodobenzene 
• 79-20-9 acetic acid methyl ester 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 201230-82-2 carbon monoxide 
• 141-78-6 ethyl acetate 

Downstream Products

• 76691-12-8 (E)-1-(4-Fluoro-phenyl)-3-morpholin-4-yl-but-2-en-1-one 
• 76691-13-9 (E)-1-(4-Fluoro-phenyl)-3-(4-phenyl-piperazin-1-yl)-but-2-en-1-one 
• 94639-17-5 4-(4-Fluoro-phenyl)-6-methyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile 
• 132360-05-5 6-(4-Fluoro-phenyl)-4-methyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile 
• 133256-49-2 2-amino-4(4'-fluorophenyl)-6-methylpyrimidine 
• 107378-03-0 1-[3-(4-Fluoro-benzoyl)-5-(4-fluoro-phenyl)-1-phenyl-1H-pyrazol-4-yl]-ethanone 
• 139262-38-7 (6-Bromo-3-methyl-4H-benzo[1,4]thiazin-2-yl)-(4-fluoro-phenyl)-methanone 
• 133116-94-6 3-amino-1-(4-fluorophenyl)but-2-en-1-one 
• 134259-95-3 4-Bromo-1-(4-fluoro-phenyl)-butane-1,3-dione 
• 120513-37-3 2-[5-(4-Fluoro-phenyl)-3-methyl-pyrazol-1-yl]-5-methyl-1H-benzoimidazole 
• 76691-11-7 (E)-1-(4-Fluoro-phenyl)-3-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-but-2-en-1-one 

Relevant academic research and scientific papers

Uncovering New Excited State Photochemical Reactivity by Altering the Course of the de Mayo Reaction

An unprecedented and previously unknown photochemical reactivity of 1,3-dicarbonyl compounds is observed with amino-alkenes leading to dihydropyrans. This novel photochemical reactivity changes the established paradigm related to the De Mayo reaction between 1,3-dicarbonyl compounds and alkenes. This new reaction allows convenient access to the Marmycin core in a single step from commercially available reactants. The origin and scope of this new photoreaction is detailed with preliminary photophysical and mechanistic investigations.

ONE-POT SYNTHESIS OF NEW FLUORINATED 4H-1,4-BENZOTHIAZINES AS POSSIBLE ANTICANCER AGENTS

One pot synthesis of fluorinated 4H-1,4-benzothiazines can be effected by the condensation and oxidative cyclization of substituted 2-aminobenzenethiols with β-diketone (p-fluorobenzoylacetone) in DMSO.The reaction is believed to proceed via an enamino-ketone system.The structures have been confirmed by their elemental,analyses and spectral studies. p-Fluorobenzoylacetone has been synthesized by Claisen condensation of ethyl acetate with p-fluoroacetophenone.

Binuclear Schiff-base zinc(II) complexes: Synthesis, crystal structures and reactivity toward ring opening polymerization of rac-lactide

Upon crystallization from DMF/diethyl ether or CH2Cl2/pyridine of tetracoordinated Zn(II) complexes containing either 4-fluorophenyl or 4-anisyl substituted O,N,O-tridentate Schiff base ligands and pyridine as auxiliary ligand, three new doubly phenoxide-bridged dimeric Zn(II) complexes were isolated and their catalytic properties for the ring opening polymerization (ROP) of rac-lactide were explored. The single-crystal XRD analysis allowed to corroborate the molecular structures of the binuclear complexes, showing that the pentacoordinated Zn(II) metal ion adopts a slightly distorted square pyramidal geometry. The basal plane Is formed by the O,N,O-donor set of the tridentate Schiff base ligand and a phenoxo bridging oxygen, while a pyridine or a DMF molecule is located at the apex of the pyramid. The binuclear complexes were employed as catalysts in the ROP of rac-lactide for polylactide (PLA) synthesis. Polymerization conditions such as reaction time, catalyst concentration and use of benzyl alcohol as cocatalyst were studied, as well as their influence on the conversion rate, average molecular weight and polydispersity of the obtained PLA. The catalyst substituted with fluorine was more reactive, but with a lower control on the molecular weight compared to the methoxy-substituted catalyst. On the other hand, the presence of pyridine as an auxiliary ligand generates an improvement in the polydispersity of PLA.

PHOTOCHEMICAL SYNTHESIS OF MARMYCIN ANALOGUES THROUGH A NEW PHOTOCHEMICAL REACTION INVOLVING CARBONYL COMPOUNDS

Photochemical reactivity of carbonyl compounds leading to the synthesis of the Marmycin core is described. The photochemical reactivity involves an excited state reaction that provides convenient access to bicyclic compounds. The disclosed reactivity is a

I2-Promoted [3+2] Cyclization of 1,3-Diketones with Potassium Thiocyanate: a Route to Thiazol-2(3H)-One Derivatives

An I2-promoted strategy has been developed for the synthesis of thiazol-2(3H)-one derivatives from 1,3-diketones with potassium thiocyanate. This [3+2] cyclization reaction involves C?S and C?N bond formation and exhibits good functional group tolerance. A series of thiazol-2(3H)-one derivatives are obtained in moderate to good yields. (Figure presented.).

Multi-stimuli-responsive fluorescence of axially chiral 4-ene-β-Diketones

A unique series of simple, smart, and chiral binaphthalene-substituted 4-ene-β-diketones molecules has been designed and prepared. Their optical properties, charge contribution, and transition process highly depend on their chemical structures. These π-conjugated materials are highly emissive in both solution and solid (emission quantum yield up to 68%), owing to the inhibition of enol-keto tautomerization and the effect of steric hindrance from binaphthalene. Through ethylenic bond hydrolysis, they can be used for not only cation/anion sensing but also chiral amino acids recognition. Moreover, at low concentrations, they have little cytotoxicity to living cells and can stain cytoplasm. Therefore, they afford a new platform in the design of multi-stimuli-responsive, smart, and chiral materials.

Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors

Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.

Synthesis of Highly Substituted Biaryls by the Construction of a Benzene Ring via in Situ Formed Acetals

Herein, we present an interesting method for the construction of a benzene ring using propargylic alcohols and 1,3-dicarbonyls, which involves three new C-C bond formations via cascade alkylation, formylation, annulation, and aromatization to make substituted biaryls. This one-pot Br?nsted acid-promoted protocol utilizes the unique reactivity of the acetal formed under the reaction conditions. Alkynyl methyl ketones could be employed instead of 1,3-dicarbonyls as they are converted to 1,3-dicarbonyls by hydration under the reaction conditions.

Tetrahydropyrimidinones/thiones stabilized by trifluoromethyl-containing β-diketones

A library of new hydropyrimidinone/thione compounds was synthesized via the classical Biginelli reaction using hydrated cerium(III) chloride as the catalyst. The presence of a trifluoromethyl or methyl group in the diketone starting material has been established to selectively control the outcome of the Biginelli reaction where one of the two possible pyrimidinone/thione compounds is formed. The results showed that the electronic effects of substituents of the diketone directly affect the product formation. The synthesized compounds were fully characterized using 1H, 13C, and two dimensional NMR (2D NMR) spectroscopy, single crystal X-ray diffractometry, FT-IR, and ESI-HDMS techniques. We also report on the uncommon one-bond correlations which were observed in the HMBC spectra and the interesting long-range heteronuclear coupling of fluorine to hydrogen and carbon.

Direct Access to Functionalized Indoles via Single Electron Oxidation Induced Coupling of Diarylamines with 1,3-Dicarbonyl Compounds

Under aerobic copper catalysis, an unprecedented direct synthesis of functionalized indoles via single electron oxidation induced coupling of diarylamines with 1,3-dicarbonyl compounds is presented. The protocol proceeds with good functional group and substrate compatibility, the use of readily available feedstocks and naturally abundant catalyst system, high step and atom efficiency, as well as selectivity, which offers a platform for accessing a new class of indoles with the potential for the discovery of functional molecules.