53842-12-9

Basic information

• Product Name: 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE
• Synonyms: 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE;1-(4-CHLOROPHENYL)-1,4-PENTANEDIONE
• CAS NO: 53842-12-9
• Molecular Formula: C₁₁H₁₁ClO₂
• Molecular Weight: 210.66
• Mol File: 53842-12-9.mol
• Article Data: 34

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE(53842-12-9)
• EPA Substance Registry System: 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE(53842-12-9)

Safety Data

• Hazardous Substances Data: 53842-12-9(Hazardous Substances Data)

Usage

Description

1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE, also known as 4-Chloro-1-phenylpentane-1,4-dione, is a chemical compound with the molecular formula C11H13ClO2. It is a diketone, which means it contains two ketone groups. 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE is often utilized in organic synthesis and serves as a building block for the preparation of various pharmaceuticals and agrochemicals. Its structure, featuring a phenyl and a chloro group, makes it a potentially valuable intermediate in the synthesis of new compounds with diverse biological activities. Consequently, 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE holds significant potential applications in the fields of chemistry and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE is used as a building block for the synthesis of various pharmaceuticals due to its unique structure and reactivity. The presence of the phenyl and chloro groups allows for the creation of new compounds with a range of biological activities, making it a valuable asset in drug discovery and development.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE is used as a starting material for the preparation of various agrochemicals. Its diketone functionality and the presence of a phenyl group make it a suitable candidate for the synthesis of compounds with potential applications in agriculture, such as pesticides and herbicides.
Used in Medicinal Chemistry:
1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE is employed as an intermediate in the field of medicinal chemistry. Its structural features enable the development of novel compounds with potential therapeutic applications, contributing to the advancement of drug discovery and the creation of new treatments for various diseases and conditions.
Used in Organic Synthesis:
As a diketone, 1-(4-CHLORO-PHENYL)-PENTANE-1,4-DIONE is used in organic synthesis for the preparation of a wide range of chemical compounds. Its reactivity and functional groups make it a versatile building block for the synthesis of various organic molecules, which can be further utilized in different industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 2642-81-1 1,1-bis(p-chlorophenyl)ethene 
• 14284-89-0 manganese(III) acetylacetonate 
• 174869-08-0 α-(3-oxobutyl)-4,4'-dichlorobenzoin 
• 64-04-0 phenethylamine 
• 504-29-0 2-aminopyridine 
• 100-46-9 benzylamine 
• 62-53-3 aniline 
• 106-47-8 4-chloro-aniline 
• 75-31-0 isopropylamine 
• 1490-24-0 4-oxo-pentanoyl chloride 
• 108-90-7 chlorobenzene 
• 104-88-1 4-chlorobenzaldehyde 
• 78-94-4 methyl vinyl ketone 
• 201230-82-2 carbon monoxide 

Downstream Products

• 123184-28-1 3-[2-(4-Chloro-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile 
• 95650-85-4 2-(4-chlorophenyl)-5-methylthiophene 
• 146204-36-6 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methyl-1H-pyrrole 
• 121363-93-7 1,2-bis(4-chlorophenyl)-5-methyl-1H-pyrrole 
• 146204-38-8 2-(4-Chloro-phenyl)-5-methyl-1-(4-nitro-phenyl)-1H-pyrrole 
• 53842-16-3 2-(4-chlorophenyl)-5-methyl-1-phenyl-1H-pyrrole 
• 26214-57-3 2-(4-chlorophenyl)-5-methyl-1H-pyrrole 
• 223661-96-9 2-(4-chloro-phenyl)-1-cyclohexyl-5-methyl-1H-pyrrole 
• 98909-79-6 3-(4-Chlorphenyl)-2-methyl-4-(2-oxopropyl)-2-cyclopenten-1-on 
• 98909-44-5 1-(4-Chlorphenyl)-2-methylen-3-(2,4,5-trimethyl-1,3-dioxolan-2-yl)-1-propanon 
• 98909-71-8 4-(4-Chlorbenzoyl)-2,6-octandion 
• 98909-72-9 3-(4-Chlorbenzoyl)-1-(2-furyl)-1,5-hexandion 
• 98909-52-5 5-(4-Chlorbenzoyl)-6-(2,4,5-trimethyl-1,3-dioxolan-2-yl)-3-hexanon 
• 98909-53-6 3-(4-Chlorbenzoyl)-1-(2-furyl)-4-(2,4,5-trimethyl-1,3-dioxolan-2-yl)-1-butanon 

Relevant articles and documents

Study on the interaction of 1,5-diaryl pyrrole derivatives with αglucosidase; synthesis, molecular docking, and kinetic study

Background: The delaying of absorption of glucose is one of the principal therapeutic approaches of type 2 diabetes. α-glucosidase inhibitors compete with the α-glucosidase enzyme activity, which helps to reduce the conversion of carbohydrates into glucose and thereby control the postprandial hyperglycemia incidence. Objective: The aim of this study was to synthesize a series of novel 1,5-diphenyl pyrrole derivatives and evaluate their in vitro α-glucosidase inhibitory activities. Methods: Compounds were synthesized through a multistep reaction and were evaluated for αglucosidase inhibitory activities. Molecular docking and kinetic studies were carried out to predict the mode of binding and mechanism of inhibition for the most active compounds, 5g and 5b, against α-glucosidase. Results: Synthesized compounds showed good in vitro α-glucosidase inhibitory activity with IC50 values in the range of (117.5 ± 3.8 to 426.0 ± 10.2 μM) as compared to acarbose, the standard drug, (750 ± 8.7 μM). Compound 5g (117.5 ± 3.8 μM) ascertained as the most potent inhibitor of α-glucosidase in a competitive mode. The binding energies of compounds 5g and 5b (119.0 ± 7.5 μM), as observed from the best docking conformations, indicate that they have a lower free binding energy (-3.26 kcal/mol and-3.0 kcal/mol, respectively) than acarbose (2.47 kcal/mol). Conclusion: The results of our study revealed that the synthesized compounds are a potential candidate for α-glucosidase inhibitors for the management of postprandial hyperglycemia for further investigation.

Design, synthesis and in-vitro anti-cancer evaluation of novel derivatives of 2-(2-methyl-1,5-diaryl-1h-pyrrol-3-yl)-2-oxo-n-(pyridin-3-yl)acetamide

Objective: Several anti-tubulin agents were introduced for the cancer treatment so far. Despite successes in the treatment of cancer, these agents cause toxic side effects, including peripheral neuropathy. Comparing anti-tubulin agents, indibulin seemed to cause minimal peripheral neuropathy, but its poor aqueous solubility and other potential clinical problems have led to its remaining in a preclinical stage. Methods: Herein, indibulin analogues were synthesized and evaluated for their in vitro anti-cancer activity using MTT assay (on the MCF-7, T47-D, MDA-MB231 and NIH-3T3 cell lines), annexin V/PI staining assay, cell cycle analysis, anti-tubulin assay and caspase 3/7 activation assay. Results: One of the compounds, 4a, showed good anti-proliferative activity against MCF-7 cells (IC50: 7.5 μM) and low toxicity on a normal cell line (IC50 > 100μM). All of the tested compounds showed lower cytotoxicity on normal cell line in comparison to reference compound, indibulin. In the annexin V/PI staining assay, induction of apoptosis in the MCF-7 cell line was observed. Cell cycle analysis illustrated an increasing proportion of cells in the sub-G-1 phase, consistent with an increasing proportion of apoptotic cells. No increase in G2/M cells was observed, consistent with the absence of anti-tubulin activity. A caspase 3/7 assay protocol showed that apoptosis induction by more potent compounds was due to activation of caspase 3. Conclusion: newly synthesized compounds exerted acceptable anticancer activity and further investigation of current scaffold would be beneficial.

Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of ?-Diketones and ?-Ketonitriles

A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)-H bond functionalization to construct new C-C bonds and C-O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to ?-diketones and ?-ketonitriles. A possible mechanism is proposed.