3160-40-5

Basic information

• Product Name: 4-CHLOROBENZYLIDENEACETONE
• Synonyms: (E)-4-(4-CHLOROPHENYL)BUT-3-EN-2-ONE;4-CHLOROBENZYLIDENEACETONE;4-(4-CHLOROPHENYL)-3-BUTEN-2-ONE;4-(4-CHLOROPHENYL)BUT-3-EN-2-ONE;(P-CHLOROBENZYLIDENE)ACETONE;(3E)-4-(4-Chlorophenyl)-3-buten-2-one;1-(4-Chlorophenyl)buten-3-one;3-Buten-2-one, 4-(p-chlorophenyl)-
• CAS NO: 3160-40-5
• Molecular Formula: C₁₀H₉ClO
• Molecular Weight: 180.63
• EINECS: 221-610-5
• Product Categories: C10;Carbonyl Compounds;Ketones
• Mol File: 3160-40-5.mol

Chemical Properties

• Melting Point: 55 °C
• Boiling Point: 145-147°C 5mm
• Flash Point: 145-147°C/5mm
• Appearance: /
• Density: 1.157 g/cm³
• Vapor Pressure: 0.00102mmHg at 25°C
• Refractive Index: 1.577
• BRN: 1100204
• CAS DataBase Reference: 4-CHLOROBENZYLIDENEACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROBENZYLIDENEACETONE(3160-40-5)
• EPA Substance Registry System: 4-CHLOROBENZYLIDENEACETONE(3160-40-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3160-40-5(Hazardous Substances Data)

Usage

Uses

Used in Photopolymer Production:
4-CHLOROBENZYLIDENEACETONE is used as a photoinitiator for the production of photopolymer materials, facilitating the polymerization process under exposure to light, which is crucial for the creation of various polymer-based products.
Used in Organic Synthesis:
In the field of organic chemistry, 4-CHLOROBENZYLIDENEACETONE is utilized as a reagent in the synthesis of a range of organic compounds, contributing to the development of new chemical entities and materials.
Used in Chemical Reactions:
As a reagent, 4-CHLOROBENZYLIDENEACETONE is employed in various chemical reactions to drive specific transformations, making it a valuable component in the synthesis of complex molecules and pharmaceuticals.
Used in Pharmaceutical Research:
4-CHLOROBENZYLIDENEACETONE is studied as a potential anti-cancer agent, with research focusing on its ability to induce cell death in cancer cells, offering a promising avenue for the development of new cancer therapies.
Used in Chemical Storage and Handling:
Due to its low toxicity and stability, 4-CHLOROBENZYLIDENEACETONE is suitable for use in chemical storage and handling processes, ensuring the safe management of this compound in industrial settings.

InChI:InChI=1/C10H9ClO/c1-8(12)2-3-9-4-6-10(11)7-5-9/h2-7H,1H3/b3-2+

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 106-96-7 propargyl bromide 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 14035-54-2 1,1-diphenyl-1-hydroxy-3-butanone 
• 873-76-7 para-Chlorobenzyl alcohol 
• 97142-86-4 1-(4-chlorophenyl)but-2-yn-1-ol 
• 134747-46-9 4-(4-chlorophenyl)-3-buten-2-ol 
• 67-63-0 isopropyl alcohol 
• 3510-99-4 3-methoxy-but-2-enoic acid ethyl ester 
• 99-91-2 para-chloroacetophenone 
• 74879-75-7 [(2R,3R)-3-(4-Chloro-phenyl)-1-methyl-aziridin-2-yl]-phenyl-methanone 

Downstream Products

• 3506-75-0 4-(4-chlorophenyl)butan-2-one 
• 34292-31-4 4-(4-chloro-phenyl)-but-3-en-2-one-phenylhydrazone 
• 59161-55-6 3,4-Bis-(4-chloro-benzyl)-hexane-2,5-dione 
• 55614-38-5 3-(4-Chloro-phenyl)-7-methoxy-1-methyl-naphthalene 
• 55614-71-6 3-(4-Chloro-phenyl)-7-methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalene 
• 55614-65-8 6-Chloro-1-(4-chloro-phenyl)-3-methyl-naphthalene 
• 130028-21-6 (E)-4-(4-Chloro-phenyl)-but-3-enoic acid methyl ester 
• 83514-42-5 1,11-Bis-(4-chloro-phenyl)-3-methyl-2,10-dihydro-1H-indolo[3,2-b]quinoline 
• 88639-77-4 3-<1-(4-Chlorphenyl)-3-oxo-butyl>-4-hydroxy-6-methyl-2H-pyran-2-on 
• 97481-63-5 8-(4-Chloro-phenyl)-4-hydroxy-1,3,6-trimethyl-1,3,7,8-tetrahydro-pyrimido[4,5-b][1,4]diazepin-2-one 
• 82756-64-7 5-(4-Chlorphenyl)-7-ethoxy-1,3,7-trimethyl-1,3,4,5,6,7-hexahydro-2H-pyrano<3,2-e>pyrimidin-2,4-dion 
• 82756-61-4 5-<1-(4-Chlorphenyl)-3-oxo-butyl>-1,3-diphenyl-hexahydropyrimidin-2,4,6-trion 
• 82756-65-8 5-(4-Chlorphenyl)-7-isopropoxy-1,3,7-trimethyl-1,3,4,5,6,7-hexahydro-2H-pyrano<3,2-e>pyrimidin-2,4-dion 
• 122252-53-3 2-Acetyl-3-(4-chloro-phenyl)-5-oxo-hexanoic acid methyl ester 

Relevant articles and documents

PQQ-dependent Dehydrogenase Enables One-pot Bi-enzymatic Enantio-convergent Biocatalytic Amination of Racemic sec-Allylic Alcohols

The asymmetric amination of secondary racemic allylic alcohols bears several challenges like the reactivity of the bi-functional substrate/product as well as of the α,β-unsaturated ketone intermediate in an oxidation-reductive amination sequence. Heading for a biocatalytic amination cascade with a minimal number of enzymes, an oxidation step was implemented relying on a single PQQ-dependent dehydrogenase with low enantioselectivity. This enzyme allowed the oxidation of both enantiomers at the expense of iron(III) as oxidant. The stereoselective amination of the α,β-unsaturated ketone intermediate was achieved with transaminases using 1-phenylethylamine as formal reducing agent as well as nitrogen source. Choosing an appropriate transaminase, either the (R)- or (S)-enantiomer was obtained in optically pure form (>98 % ee). The enantio-convergent amination of the racemic allylic alcohols to one single allylic amine enantiomer was achieved in one pot in a sequential cascade.

Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements

Systematic evaluation of 1,5-dienes bearing 3,3-electron-withdrawing groups and 4-methylation results in the discovery of a Cope rearrangement for Meldrum's acid-containing substrates that have unexpectedly favorable kinetic and thermodynamic profiles. The protocol is quite general due to a concise and convergent synthesis from abundant starting materials. Furthermore, products with an embedded Meldrum's acid moiety are prepared, which, in turn, can yield complex amides under neutral conditions. We have now expanded the scope of the reductive Cope rearrangement, which, via chemoselective reduction, can promote thermodynamically unfavorable [3,3] sigmatropic rearrangements of 3,3-dicyano-1,5-dienes to form reduced Cope rearrangement products. The Cope rearrangement is found to be stereospecific and can yield enantioenriched building blocks when chiral, nonracemic 1,3-disubstituted allylic electrophiles are utilized. We expand further the use of Cope rearrangements for the synthesis of highly valuable building blocks for complex- and drug-like molecular synthesis.

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents

A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen–Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16–5.45 μM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways.

Organocatalytic diastereo- And enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyrans

Tetrahydropyran derivatives are found in bioactives, and introduction of the trifluoromethyl group into molecules often improves biofunctions. Here we report diastereo- and enantioselective oxa-hetero-Diels-Alder reactions catalyzed by amine-based catalyst systems that afford trifluoromethyl-substituted tetrahydropyranones. Catalyst systems and conditions suitable for the reactions to provide the desired diastereomer products with high enantioselectivities were identified, and various trifluoromethyl-substituted tetrahydropyranones were synthesized with high diastereo- and enantioselectivities. Mechanistic investigation suggested that the reactions involve a [4 + 2] cycloaddition pathway, in which the enamine of the enone acts as the diene and the ketone carbonyl group of the aryl trifluoromethyl ketone acts as the dienophile. In this study, tetrahydropyran derivatives with the desired stereochemistry that are difficult to synthesize by previously reported methods were concisely obtained, and the range of tetrahydropyran derivatives that can be synthesized was expanded. This journal is

A bioinspired microreactor with interfacial regulation for maximizing selectivity in a catalytic reaction

We report a bioinspired emulsion microreactor composed of an electrical double layer to mimic the functions of cell membranes. This "artificial cell"can modulate the phase-oriented transport of reagents at the oil-liquid interface via the electrical double layer, affording a powerful tool to optimize the selectivity in a catalytic reaction. This journal is

NOVEL SMALL MOLECULES THAT BIND AND/OR MODULATE DIFFERENTFORMS OF TAU OLIGOMERS

The present invention relates to novel small molecules of Formulas I, II, III, Ilia, Illb, and IV and pharmaceutically acceptable salts thereof, as well as the preparation and the use thereof.

Design, synthesis and biological evaluation of novel diaryl pyrazole derivatives as anticancer agents

Cancer is one of the major causes of mortality all around the world. Globally, nearly 1 in 6 deaths is due to cancer. Researchers are trying to synthesize new anticancer agents. Previous studies demonstrated that some pyrazole derivatives could be considered as potential anticancer agents. Herein, ten novel derivatives of 1,5-diarylpyrazole were synthesized in four step reactions and cytotoxic activity was investigated by MTT cell viability assay. All of the compounds were characterized by1H NMR and13C NMR and their purity was confirmed by elemental analysis. The cytotoxicity was determined against three cancerous cell lines (HT-29, U87MG and MDA-MB 468) and AGO1522 as a normal cell line. Compound 5a showed the best cytotoxic activity on cancerous cell lines in comparison to paclitaxel. Annexin V/ PI staining assay also showed that compounds 5a and 5i would lead to significant apoptosis induction in MDA-MB 486 cell line.

THIAZOLE DERIVATIVES AS PROTEIN SECRETION INHIBITORS

Provided herein are secretion inhibitors, such as inhibitors of Sec61, methods for their preparation, related pharmaceutical compositions, and methods for using the same, wherein the compound has a structure of Formula (I), (II), or (III).

Boosting multiple photo-assisted and temperature controlled reactions with a single redox-switchable catalyst: Solvents as internal substrates and reducing agent

An alternative and economically viable process for the synthesis of β-aryl enals, enones and the aryl amines has been developed by partial oxidation of ethanol, isopropanol and N, N-dimethyl formamide (DMF). The formation of β-aryl enals, enones and the aryl amines was catalyzed by a mixed metal oxides layer of cobalt and chromium supported on halloysite nanotubes, designated as CoCr2O4-HNT. The C[sbnd]C and C[sbnd]N bond formation reactions were found to be influenced by temperature and the nature of base. The condensation of aldehyde with in situ generated acetaldehyde by ethanol oxidation forming β-aryl enals occurred selectively at 120 °C. The partial oxidation of isopropanol to acetone and its condensation with aldehydes forming β-aryl enones occurred at room temperature. Increase in temperature caused the liberation of hydrogen gas from isopropanol and allowed the reversible reduction of aldehydes to alcohols. Increase in temperature in isopropanol and increase in base concentration in ethanol causes the selective reduction of aldehydes to alcohols. Besides being active for the Claisen-Schmidt type of reactions and the aryl halides amination process, the synthesized catalyst was also found to be highly active for the photocatalytic oxidation of benzyl alcohols in absence of any external oxidizing agent. The positive holes (h+) generated at the Co(II) site as evident from EPR analysis was considered to be responsible for high photocatalytic activity of the material reducing the recombination rate of holes and electrons (e?). Density Functional Theory calculations were performed to understand the mechanism of ethanol oxidation to acetaldehyde.