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3-(4-Chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one, also known as 4'-chloro-4-methoxy-alpha-methylstilbene, is an organic compound characterized by a phenylpropiolate structure. It features a central prop-2-en-1-one (alpha-methylstilbene) core, with a 4-chlorophenyl group attached at the 3-position and a 4-methoxyphenyl group at the 1-position. This molecule is a derivative of stilbene, which is a class of organic compounds with potential applications in various fields, including pharmaceuticals and materials science. The presence of the chloro and methoxy substituents on the phenyl rings can influence the compound's reactivity, solubility, and other physical and chemical properties, making it a subject of interest for synthetic chemistry and potential applications in specialty chemicals.

6552-68-7

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6552-68-7 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 6552-68-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,5,5 and 2 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 6552-68:
(6*6)+(5*5)+(4*5)+(3*2)+(2*6)+(1*8)=107
107 % 10 = 7
So 6552-68-7 is a valid CAS Registry Number.
InChI:InChI=1/C16H13ClO2/c1-19-15-9-5-13(6-10-15)16(18)11-4-12-2-7-14(17)8-3-12/h2-11H,1H3

6552-68-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

1.2 Other means of identification

Product number -
Other names 4-chloro-4'-methoxy-3-nitro-benzophenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6552-68-7 SDS

6552-68-7Relevant academic research and scientific papers

Synthesis of lithium/cesium-Zagronas from zagrosian natural asphalt and study of their activity as novel, green, heterogeneous and homogeneous nanocatalysts in the Claisen–Schmidt and Knoevenagel condensations

Soleiman-Beigi, Mohammad,Ghalavand, Saba,Venovel, Hadis Gholami,Kohzadi, Homa

, p. 3267 - 3279 (2021/06/17)

A novel, heterogeneous and homogeneous basic nanocatalysts were synthesized by grafting of lithium and cesium on zagrosian natural asphalt sulfonate (Li/Cs-Zagronas). The activity of these catalysts was examined in the Claisen–Schmidt and Knoevenagel condensations under mild reaction conditions. Li/Cs-Zagronas were characterized by FT-IR spectroscopy, scanning electron microscopy, X-ray diffraction, energy-dispersive spectroscopy, inductively coupled plasma and thermogravimetric analysis techniques. These nanocatalysts were removed by simple filtration and reused several times without any deterioration of activity.

Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water

Tanemura, Kiyoshi,Rohand, Taoufik

supporting information, (2021/02/27)

A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.

Synthesis, characterization, molecular docking and in vitro anticancer activity of 3-(4-methoxyphenyl)-5-substituted phenyl-2-pyrazoline-1-carbothioamide

Sahu, Benupani,Rajapandi,Maji, Avik,Paul, Abhik,Singha, Tanushree,Maity, Tapan Kumar

, p. 1648 - 1658 (2021/06/26)

In the present study, eight numbers of new 3-(4-methoxy phenyl)-5-substituted phenyl-2-pyrazoline-1-carbothioamide (5a-h) have been synthesized from 1-(4-methoxy phenyl)-3-(substituted phenyl)-prop-2-en-1-one (3a-h) and structurally characterized by using FT-IR,1H NMR,13C NMR, Mass and Elemental analysis. The synthesized molecules were biologically eval-uated for their in vitro anticancer activity against human breast adenocar-cinoma (MCF-7), liver cancer (Hep-G2) and leukaemia cancer (K-562) cell line using Sulforhodamine B (SRB) bioassay technique. From the all synthesized compounds 5a, 5c, 5d, and 5e exhibited potent anticancer activity (GI50= 50=44.5μg/ml) and Adriamycin (ADR) (GI50= 10μg/ml) on MCF-7 cell lines. Besides this, all the synthesized compounds have exhibited moderate activity against human liver cancer (Hep-G2) and leukaemia cancer (K-562) cell lines. In addition, molecular docking studies were also explored in order to study the probable binding specificity into the active site of Epidermal Growth Factor Receptor tyrosine kinase (EGFR) (PDB ID: 1M17) using Molegro Virtual Docker Evaluation 2013 6.0.1 (MVD). Based on the molecular docking result, it was found that compound 5a exhibited the best interaction with the above target (i.e., EGFR) by interacting with specific amino acid residues such as: Thr 766, Gin 767, Thr 830, Cys 575, Ala 719 and Met 769.

Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones

Gao, Pan-Pan,Yan, Dong-Mei,Bi, Ming-Hang,Jiang, Min,Xiao, Wen-Jing,Chen, Jia-Rong

supporting information, p. 14195 - 14201 (2021/09/20)

A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.

Method using Ti (III) complex catalytic alkyne selective hydrogenation reduction to prepare chalcone compounds

-

Paragraph 0014; 0015; 0016; 0017; 0018; 0029; 0030; 0031;..., (2021/09/26)

The invention discloses a method for preparing chalcone compounds through selective hydrogenation of Ti (III) complexes to prepare chalcone compounds, wherein zinc powder is used as a catalyst, zinc powder is a reducing agent, triethylamine hydrochloride is a proton source, and an alkyne and triethylamine hydrochloride are subjected to radical selective addition reaction under the protection of inert gas to generate chalcone compounds. The reaction condition is mild, the operation is simple, the reaction time is short, the reaction product is single, the atom economy is high, and only the product needs to be separated by simple column chromatography after the reaction is finished. The chalcone compound has wide biological activity and medicinal value.

Potassium Natural Asphalt Sulfonate (K-NAS): Synthesis and characterization as a new recyclable solid basic nanocatalyst and its application in the formation of carbon–carbon bonds

Falah, Saeid,Soleiman-Beigi, Mohammad,Kohzadi, Homa

, (2020/07/06)

In this research, we synthesized and characterized a new heterogeneous basic nanocatalyst and its catalytic application was studied in the Claisen-Schmidt and Knoevenagel condensations. In order to prepare this nanocatalyst, first, the Iranian natural asphalt was sulfonated with the concentrated sulfuric acid and then, converted to the potassium natural asphalt sulfonate (K-NAS). In order to characterization of the nanocatalyst, used of FT-IR spectroscopy, scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), inductively coupled plasma (ICP) and thermogravimetric analysis (TGA) techniques. This new basic heterogeneous nanocatalyst have advantages such as being eco-friendly, huge specific surface area, high reactivity and recyclability.

Three Step Synthesis of Fully and Differently Arylated Pyridines

Arita, Mao,Yokoyama, Soichi,Asahara, Haruyasu,Nishiwaki, Nagatoshi

, p. 466 - 474 (2020/01/25)

Condensation of β-(2-pyridyl)enamine and α,β-unsaturated ketone in the presence of FeCl3 under air afforded highly substituted pyridines. In this transformation, FeCl3 acted as not only an acid catalyst but also an oxidant for the in

Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature

Tamuli, Kashyap J.,Sahoo, Ranjan K.,Bordoloi, Manobjyoti

supporting information, p. 20956 - 20965 (2020/12/31)

Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.

Convenient Synthesis of Novel Chalcone and Pyrazoline Sulfonamide Derivatives as Potential Antibacterial Agents

Bonakdar,Sadeghi,Aghaei,Beheshtimaal,Nazifi,Massah

, p. 371 - 381 (2020/06/30)

Abstract: Novel chalcone sulfonamide derivatives were synthesized starting from benzophenones and aldehydes in 3 steps. Also, (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one was converted to different pyrazoline in four steps. The synthesis of s

Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia-derived cells: Role of PKCβ

Corsini, Emanuela,Facchetti, Giorgio,Esposito, Sara,Maddalon, Ambra,Rimoldi, Isabella,Christodoulou, Michael S.

, (2020/05/16)

In this study, a series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia-derived cell line, CCRF-CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was tested against the same cancer cell line. Furthermore, four of these derivatives (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 μM), were selected for further investigation regarding the modulation of the protein expression of RACK1 (receptor for activated C kinase), protein kinase C (PKC)α and PKCβ, and their action on the cell cycle level. The cell cycle analysis indicated a block in the G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in the S phase, with no indication of apoptosis (sub-G0/G1 phase). Compounds 4 and 8 showed a statistically significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ, as assessed by treating cells with a selective PKCβ activator, indicated that the observed antiproliferative effect is likely to be mediated through PKCβ induction.

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