621-16-9

Basic information

• Product Name: (2E)-1-phenyl-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one
• Synonyms: 1-Phenyl-3-(3-(trifluoromethyl)phenyl)-2-propen-1-one
• CAS NO: 621-16-9
• Molecular Formula: C₁₆H₁₁F₃O
• Molecular Weight: 276.2531
• Mol File: 621-16-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 356.2°C at 760 mmHg
• Flash Point: 187.2°C
• Density: 1.236g/cm³
• Vapor Pressure: 2.98E-05mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: (2E)-1-phenyl-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-phenyl-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one(621-16-9)
• EPA Substance Registry System: (2E)-1-phenyl-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one(621-16-9)

Safety Data

• Hazardous Substances Data: 621-16-9(Hazardous Substances Data)

Usage

Description

(2E)-1-phenyl-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one is a chemical compound with aromatic properties, commonly used in organic synthesis and pharmaceutical research. It is a ketone compound with a molecular formula of C15H11F3O and a molecular weight of 270.24 g/mol. This chemical is characterized by its double bond structure and contains a phenyl group and a trifluoromethyl group, making it a valuable building block in the synthesis of various drugs and materials. Its unique structure and properties make it an important intermediate in the development of organic compounds and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
(2E)-1-phenyl-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one is used as a building block for the synthesis of various drugs and materials. Its unique structure and properties make it an important intermediate in the development of pharmaceuticals.
Used in Organic Synthesis:
(2E)-1-phenyl-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one is used as a valuable intermediate in the synthesis of various organic compounds. Its aromatic properties and double bond structure make it a useful component in the creation of new molecules and materials.

Upstream product

• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 98-86-2 acetophenone 
• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 

Downstream Products

• 111026-62-1 4-oxo-4-phenyl-2-<3-(trifluoromethyl)phenyl>butyronitrile 
• 111059-95-1 4-oxo-4-phenyl-2-<3-(trifluoromethyl)phenyl>butyric acid 
• 111026-68-7 2-(3-Trifluoromethyl-phenyl)-3,4-dihydro-2H-naphthalen-1-one 
• 111026-54-1 4-phenyl-2-<3-(trifluoromethyl)phenyl>butyric acid 
• 111026-64-3 methyl 4-oxo-4-phenyl-2-<3-(trifluoromethyl)phenyl>butyrate 
• 1221402-59-0 (R)-2-[(S)-3-oxo-3-phenyl-1-(3-(trifluoromethyl)phenyl)propyl]cyclopentanone 
• 1273593-11-5 (S)-2-[(R)-3-oxo-3-phenyl-1-(3-(trifluoromethyl)phenyl)propyl]cyclopentanone 
• 1318796-25-6 C₂₃H₁₉F₃N₂O₂ 
• 95465-73-9 1-phenyl-3-(3-(trifluoromethyl)phenyl)propan-1-one 

Relevant articles and documents

Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B

A library of monosubstituted chalcones (1-17) bearing electron-donating and electron-withdrawing groups on both aromatic rings were selected. The cell viability on human tumor cell lines was evaluated first. The compounds unable to induce detectable cytotoxicity (1, 13, and 14) were tested using the monoamine oxidase (MAO) activity assay. Interestingly, they inhibit MAO-B, acting as competitive inhibitors, with 13 and 14 showing the best profiles. In particular, 13 exhibited a potency higher than that of safinamide, taken as a reference. Docking studies and crystallographic analysis showed that in human MAO-B 13 binds with the halogen-substituted aromatic ring in the entrance cavity, similar to safinamide, whereas 14 is accommodated in the opposite way. The main conclusion of this cell biology, biochemistry, and structural study is to highlights 13 as a chalcone derivative that is worth consideration for the development of novel MAO-B-selective inhibitors for the treatment of neurodegenerative diseases.

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

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.

Inhibition of LPS-stimulated ROS production by fluorinated and hydroxylated chalcones in RAW 264.7 macrophages with structure-activity relationship study

Based on the importance of the previous fluorinated and/or hydroxylated chalcones studies, thirty-six compounds were designed as phenyl or hydroxyphenyl bearing fluoro, trifluoromethyl or trifluoromethoxy phenyl propenones and synthesized by applying modified Claisen-Schmidt condensation reaction as a single step. Inhibitory effects of the synthesized compounds on ROS production stimulated by LPS in RAW 264.7 macrophage were evaluated. Structure-activity relationship (SAR) study revealed that the compounds possessing para-hydroxyphenyl group combined with meta-fluoro or meta-trifluoromethyl phenyl group, and meta/para-hydroxyphenyl group combined with ortho-trifluoromethoxyphenyl group have an essential role in inhibiting the LPS-stimulated ROS production in RAW 264.7 macrophages. The most significant inhibitory effect on LPS-stimulated ROS production in RAW 264.7 macrophages was observed in compound 30 that possessed para-hydroxyphenyl group along with ortho-trifluoromethoxyphenyl group.