18362-49-7

Basic information

• Product Name: 1,3-Bis(4-chlorophenyl)propane-1,3-dione
• Synonyms: 1,3-Bis(4-chlorophenyl)propane-1,3-dione;1,3-BIS(4-CHLOROPHENYL)-1,3-PROPANEDIONE
• CAS NO: 18362-49-7
• Molecular Formula: C₁₅H₁₀Cl₂O₂
• Molecular Weight: 293.1447
• Mol File: 18362-49-7.mol

Chemical Properties

• Melting Point: 159 °C(Solv: acetic acid (64-19-7); ethanol (64-17-5))
• Boiling Point: 454°Cat760mmHg
• Flash Point: 191.2°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 1.97E-08mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.37±0.13(Predicted)
• CAS DataBase Reference: 1,3-Bis(4-chlorophenyl)propane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(4-chlorophenyl)propane-1,3-dione(18362-49-7)
• EPA Substance Registry System: 1,3-Bis(4-chlorophenyl)propane-1,3-dione(18362-49-7)

Safety Data

• Hazardous Substances Data: 18362-49-7(Hazardous Substances Data)

Usage

Uses

Used in Pesticide Industry:
1,3-bis(4-chlorophenyl)propane-1,3-dione is used as an insecticide for controlling a wide range of pests, particularly in agricultural settings. Its application is due to its effectiveness in disrupting the nervous systems of insects, leading to their paralysis and eventual death.
Used in Pharmaceutical Industry:
1,3-bis(4-chlorophenyl)propane-1,3-dione is used as a starting material in the synthesis of various pharmaceutical compounds. Its chemical structure allows for the creation of new drugs with potential therapeutic applications.
Used in Research and Development:
1,3-bis(4-chlorophenyl)propane-1,3-dione is utilized in scientific research to study the effects of organochlorine compounds on the environment and human health. This helps in understanding the potential risks associated with their use and in developing safer alternatives.

InChI:InChI=1/C15H10Cl2O2/c16-12-5-1-10(2-6-12)14(18)9-15(19)11-3-7-13(17)8-4-11/h1-8H,9H2

Upstream product

• 7335-27-5 ethyl 4-chlorobenzoate 
• 99-91-2 para-chloroacetophenone 
• 122-01-0 4-chloro-benzoyl chloride 
• 623-03-0 4-Cyanochlorobenzene 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 62375-97-7 Bis-(4-chlor-benzoyl)-methanenol 
• 109-77-3 malononitrile 
• 104-88-1 4-chlorobenzaldehyde 
• 7499-07-2 4-chloro-2-methylbenzoic acid 
• 74-11-3 para-chlorobenzoic acid 
• 108-05-4 vinyl acetate 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 5925-67-7 methyl chlorobenzenethiocarboxylate 

Downstream Products

• 167702-24-1 Dithio-bis-(bis-(4-chlorobenzoyl)-methane) 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 35333-17-6 1,5-bis-(4-chloro-phenyl)-pentane-1,5-dione 
• 99-91-2 para-chloroacetophenone 
• 170647-11-7 2,4-Bis-(4-chloro-benzoyl)-1,5-bis-(4-chloro-phenyl)-pentane-1,5-dione 
• 33074-16-7 2,2-dibromo-1,3-bis(4-chlorophenyl)propane-1,3-dione 
• 3282-33-5 1-(4-chlorophenyl)-2-diazoethanone 
• 1000405-85-5 2,3,5-tris(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrrole 
• 1052176-07-4 1,3-bis(4-chlorophenyl)-2-(1-phenylethyl)propane-1,3-dione 
• 1127405-07-5 1-(4-chloro-phenyl)-2-(morpholin-4-yl)ethane-1,2-dione 
• 128592-62-1 1-(4-chlorophenyl)-2-( piperidin-1-yl)ethane-1,2-dione 
• 84039-66-7 4-chloro-N,N-diethyl-α-oxo-benzeneacetamide 
• 21368-28-5 4-chlorobenzoyl azide 

Relevant articles and documents

Triboluminescence of centrosymmetric lanthanide β-diketonate complexes with aggregation-induced emission

Triboluminescence (TL) is a form of light emission induced upon mechanical forces on the material. However, our understanding of this phenomenon is still unclear and more examples are therefore needed in order to elucidate its mechanism. In this work, two

Br?nsted acid-catalyzed enantioselective addition of 1,3-diones to in situ generated N-acyl ketimines

A Br?nsted acid-catalyzed asymmetric Mannich-type addition of 1,3-diones to cyclic N-acyl ketimines is reported for the synthesis of enantioenriched isoindolinones. Various dicarbonyl-substituted isoindolinones bearing a quaternary carbon stereocenter were synthesized with excellent yields (up to 98%) and moderate to high enantioselectivities (up to 95% ee), and most of them possess a fluorine atom at the reactive center. Furthermore, the synthetic utility of the protocol has been demonstrated by the debenzoylation of the product.

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.).

Organocatalytic Asymmetric Cascade Michael-acyl Transfer Reaction between 2-Fluoro-1,3-diketones and Unsaturated Thiazolones: Access to Fluorinated 4-Acyloxy Thiazoles

Quinine derived bifunctional urea catalyzed cascade Michael-acyl transfer reaction of 5-alkenyl thiazolones and monofluorinated β-diketones has been developed. The fluorine containing 4-acyloxy thiazoles were synthesized in high yields and good diastereo-and excellent enantioselectivities. Synthetic transformations, including synthesis of 4-hydroxy thiazoles, have been demonstrated.

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

Enolization rates control mono-: Versus di-fluorination of 1,3-dicarbonyl derivatives

Fluorine-containing 1,3-dicarbonyl derivatives are essential building blocks for drug discovery and manufacture. To understand the factors that determine selectivity between mono- and di-fluorination of 1,3-dicarbonyl systems, we have performed kinetic studies of keto-enol tautomerism and fluorination processes. Photoketonization of 1,3-diaryl-1,3-dicarbonyl derivatives and their 2-fluoro analogues is coupled with relaxation kinetics to determine enolization rates. Reaction additives such as water accelerate enolization processes, especially of 2-fluoro-1,3-dicarbonyl systems. Kinetic studies of enol fluorination with Selectfluor and NFSI reveal the quantitative effects of 2-fluorination upon enol nucleophilicity towards reagents of markedly different electrophilicity. Our findings have important implications for the synthesis of α,α-difluoroketonic compounds, providing valuable quantitative information to aid in the design of fluorination and difluorination reactions.

1,2-Diazacyclopentane-3,5-diyl Diradicals: Electronic Structure and Reactivity

Localized singlet diradicals are key intermediates in bond homolysis. A thorough study of the reactive species is needed to clarify the mechanisms of the homolytic bond cleavage and formation processes. In general, the singlet diradicals are quite short-lived because of the fast radical-radical coupling reactions. The short-lived characteristic has retarded the thorough study on bond homolysis. In this study, a new series of long-lived singlet diradicals, viz., 1,2-diazacyclopentane-3,5-diyl, were identified, and their electronic structures and novel reactivities were thoroughly studied using laser-flash photolysis (LFP), product analysis, and computational studies. A direct observation of the thermal equilibration (fast process) between the singlet diradicals and the corresponding ring-closing compounds was undertaken on the submicrosecond time scale. The solvent and substituent effects on the equilibration constant and rate constants for the ring-closing reaction and ring-opening reaction clarify the novel nitrogen-atom effect on the localized singlet 1,3-diyl diradicals. Two types of alkoxy-migrated compounds, 9 and 10, were isolated with high yields as the final products. Crossover, spin-trapping, and LFP experiments for the formation of alkoxy-group migration products (i.e., 9 versus 10) revealed the unique temperature effect on the product ratio of the two types of alkoxy-migration products. The temperature-insensitive intersystem crossing process (slow process, millisecond time scale) was found to be a key step in the formation of 9, which is an entropy-controlled pathway. An intramolecular migration process was identified for the formation of 10 that was accelerated by a polar solvent in an enthalpy-controlled process. This unique heteroatom effect has opened up a new series of localized singlet diradicals that are crucial intermediates in bond homolysis.

Reinventing the de Mayo reaction: Synthesis of 1,5-diketones or 1,5-ketoesters via visible light [2+2] cycloaddition of β-diketones or β-ketoesters with styrenes

A visible light mediated De Mayo reaction between 1,3-diketones and styrenes following a [2+2] cycloaddition pathway via a photosensitization mechanism gives access to 1,5-diketones. The reaction has been applied to substituted styrenes and aryl- and alkyl-substituted ketones. Moreover, the method converts β-ketoesters, β-amido esters, and β-cyano ketones. Seven membered rings, a frequent structural motif of natural products, are also accessible using this methodology.

PhIO/Et3N ? 3HF-Mediated Formation of Fluorinated 2H-Azirines via Domino Fluorination/Azirination Reaction of Enamines

A variety of enamine carboxylic esters and enaminones were converted to the biologically interesting fluorinated 2H-azirines through reactions with PhIF2 generated in situ by PhIO and Et3N ? 3HF in 1,2-dichroloethane, which features the hypervalent iodine reagents-mediated introduction of fluorine atom and formation of the 2H-azirine skeleton under metal-free conditions. The domino reaction is postulated to proceed via a PhIF2-mediated oxidative fluorination and a subsequent azirination of the fluorinated enamine intermediates. (Figure presented.).

Organic base-catalysed solvent-tuned chemoselective carbotrifluoromethylation and oxytrifluoromethylation of unactivated alkenes

An unprecedented and efficient organic base-catalysed highly chemoselective carbo- and oxytrifluoromethylation of unactivated alkenes with Togni's reagent was developed. The switchable chemoselectivity was tuned by simply changing the organic base catalyst and solvent. Mechanistic studies indicated that a radical cyclization pathway for carbotrifluoromethylation in DMSO and a carbocation pathway for oxytrifluoromethylation in DCE were probably involved.