257872-87-0

Basic information

• Product Name: 4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID
• Synonyms: 4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID;(E)-3-(4-CHLORO-3-TRIFLUOROMETHYL-PHENYL)-ACRYLIC ACID;RARECHEM BK HW 0183;3-(4-Chloro-3-(trifluoroMethyl)phenyl)acrylic acid
• CAS NO: 257872-87-0
• Molecular Formula: C₁₀H₆ClF₃O₂
• Molecular Weight: 250.6
• Product Categories: Cinnamic acid
• Mol File: 257872-87-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID(257872-87-0)
• EPA Substance Registry System: 4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID(257872-87-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 257872-87-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID is used as an intermediate for the synthesis of various organic compounds, particularly in the development of pharmaceutical ingredients. Its unique chemical properties and reactivity contribute to the creation of new drugs and therapeutic agents.
Used in Chemical Industry:
In the chemical industry, 4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID serves as a key intermediate, facilitating the production of a range of organic compounds for diverse applications.
Used in Organic Synthesis:
4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID is utilized as a building block in organic synthesis, where its functional groups and chemical reactivity are leveraged to construct complex organic molecules for various purposes.
Used in Material Science:
4-CHLORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID may also find applications in material science, where its unique properties could be harnessed to develop new materials with specific characteristics for use in different industries.

Upstream product

• 141-82-2 malonic acid 
• 34328-46-6 4-chloro-3-(trifluoromethyl)benzaldehyde 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 695187-18-9 methyl 3-(4-chloro-3-trifluoromethylphenyl)acrylate 
• 57661-53-7 3-(4-chloro-3-trifluoromethyl-phenyl)-N-(2,4-dioxo-imidazolidin-1-yl)-acrylamide 

Relevant articles and documents

Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst

We have developed an efficient photocatalytic synthesis of coumarin derivativesviaa tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives dimerized lignan-type products.

Discovery of 3-cinnamamido-n-substituted benzamides as potential antimalarial agents

Background: Malaria is one of the most devastating parasitic diseases, yet the discovery of antimalarial agents remains profoundly challenging. Very few new antimalarials have been developed in the past 50 years, while the emergence of drug-resistance continues to appear. Objective: This study focuses on the discovery, design, synthesis, and antimalarial evaluation of 3- cinnamamido-N-substituted benzamides. Methods: In this study, a screening of our compound library was carried out against the multidrugsensitive Plasmodium falciparum 3D7 strain. Derivatives of the hit were designed, synthesized and tested against P. falciparum 3D7 and the in vivo antimalarial activity of the most active compounds was evaluated using the method of Peters’ 4-day suppressive test. Results: The retrieved hit compound 1 containing a 3-cinnamamido-N-substituted benzamide skeleton showed moderate antimalarial activity (IC50 = 1.20 μM) for the first time. A series of derivatives were then synthesized through a simple four-step workflow, and half of them exhibited slightly better antimalarial effect than the precursor 1 during the subsequent in vitro assays. Additionally, compounds 11, 23, 30 and 31 displayed potent activity with IC50 values of approximately 0.1 μM, and weak cytotoxicity against mammalian cells. However, in vivo antimalarial activity is not effective, which might be ascribed to the poor solubility of these compounds. Conclusion: In this study, the phenotypic screen of our compound library resulted in the first report of a 3-cinnamamide framework with antimalarial activity and 40 derivatives were then designed and synthesized. Subsequent structure-activity studies showed that compounds 11, 23, 30 and 31 exhibited the most potent and selective activity against the P. falciparum 3D7 strain with IC50 values around 0.1 μM. Our work herein sets another example of phenotypic screen-based drug discovery, leading to potentially promising candidates of novel antimalarial agents once given further optimization.

Synthesis and biological evaluation of N-(4-phenylthiazol-2-yl)cinnamamide derivatives as novel potential anti-tumor agents

In this study, a series of novel N-(4-phenylthiazol-2-yl)cinnamamide derivatives (7a-8n) were synthesized and evaluated for their anti-proliferative activities in vitro by MTT assay and a possible antitumor mechanism was also explored. SAR analysis showed that steric effects played an important role on the anti-tumor activity. The most potent analogue 8f showed excellent inhibitions on the K562, Bel7402, A549 and Jurkat cells ranging from sub-micromolar to nanomolar concentration. Compound 8f inhibited Jurkat cells with an IC50 value of 0.035 μM with no apparent toxicity in different non-cancerous cells. Furthermore, it was suggested that the possible mechanism of 8f might be associated with inducing cancer cell apoptosis following flow cytometer analysis and Hoechst 33358 staining assays.

PHARMACEUTICALLY ACTIVE BENZOXAZOLE, BENZTHIAZOLE AND BENZIMIDAZOLE ACID DERIVATIVES

Compounds of formula (I): wherein R1, R2 and R3 are independently, hydrogen, halogen, CF3, OR6, NR7R8, NR8COR10, NR8SO2R10 or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkoxy or NR7R8; R4 is NR8CONR8R9, NR8COR9, NR8SO2R9, or W-CONR8R9, where W is a bond, C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene; and R5 is Formula (A) methods for their synthesis, pharmaceutical compositions comprising them and their use in medicine, in particular for the treatment of cancer.