42996-84-9

Basic information

• Product Name: trans-3-(4-Methoxyphenyl)-acryloyl chloride
• Synonyms: trans-3-(4-Methoxyphenyl)-acryloyl chloride;(E)-3-(4-methoxyphenyl)prop-2-enoyl chloride
• CAS NO: 42996-84-9
• Molecular Formula: C₁₀H₉ClO₂
• Molecular Weight: 196.63
• Mol File: 42996-84-9.mol
• Article Data: 186

Chemical Properties

• Appearance: /
• CAS DataBase Reference: trans-3-(4-Methoxyphenyl)-acryloyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-(4-Methoxyphenyl)-acryloyl chloride(42996-84-9)
• EPA Substance Registry System: trans-3-(4-Methoxyphenyl)-acryloyl chloride(42996-84-9)

Safety Data

• Hazard Codes: C
• Statements: 22-34-42/43
• Safety Statements: 22-24-26-36/37/39-45
• Hazardous Substances Data: 42996-84-9(Hazardous Substances Data)

Usage

General Description

Trans-3-(4-Methoxyphenyl)-acryloyl chloride is a chemical compound with the molecular formula C11H9ClO2. It is predominantly used in the field of organic synthesis. Like other acryloyl compounds, it has a carbon-carbon double bond and a carboxyl group, making it a reactive substance. The "trans-3" in its name denotes the spatial arrangement of the molecule, while “4-Methoxyphenyl” refers to the presence of a methoxy group attached to a phenyl group at the fourth carbon atom. The term "chloride" indicates the presence of a chlorine atom.Overall, this chemical is typically utilized as a key component in the production of various polymers, composites, and adhesives in the industrial sector.

Upstream product

• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 7400-08-0 para-coumaric acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 79-37-8 oxalyl dichloride 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 7400-08-0 p-Coumaric Acid 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 340258-61-9 3-(4-methoxyphenyl)-N-(4-methoxyphenyl)prop-(2E)-enamide 
• 832-01-9 methyl p-methoxycinnamate 
• 480-43-3 5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one 
• 95273-01-1 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethylchromen-4-one 
• 42996-87-2 2-acetyl-5-(4-methoxy-phenyl)-3-oxo-pent-4-enoic acid methyl ester 
• 36650-51-8 4-methoxycinnamic acid amide 
• 57260-55-6 1-(4-methoxy-cinnamoyl)-2,6-dimethyl-4-(5-phenyl-2-oxo-2-oxazolin-2-yl)-piperazin 
• 57260-04-5 1-[5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-oxazol-2-yl]-4-[3-(4-methoxy-phenyl)-acryloyl]-piperazine 
• 63293-94-7 C₂₄H₂₉NO₅ 
• 30392-19-9 (Z)-3-(4-Methoxy-phenyl)-acrylic acid 2,6-di-tert-butyl-4-methyl-phenyl ester 
• 60576-90-1 (E)-3-(4-Methoxy-phenyl)-acrylic acid 2-dimethylamino-2-phenyl-butyl ester 
• 57260-74-9 N-(tert.-Butyloxycarbonyl)-N'-(4-methoxycinnamoyl)ethylenediamin 
• 72129-93-2 3,3'-bis-(4-methoxy-phenyl)-1,1'-benzo[1,2-d;4,5-d']bisoxazole-2,6-diyl-bis-propenone 
• 57260-43-2 1-benzothiazol-2-yl-4-[3-(4-methoxy-phenyl)-acryloyl]-piperazine 

Relevant articles and documents

Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives

This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.

Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes

β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

Practical access to fluorescent 2,3-naphthalimide derivatives: Via didehydro-Diels-Alder reaction

A practical and efficient approach for the synthesis of fluorescent 2,3-naphthalimide derivatives has been developed from readily available starting materials via an intramolecular didehydro-Diels-Alder reaction, which proceeded well under room temperature, exhibiting a wide substrate scope and good functional group tolerance. The practicability of this methodology has been verified by one-step synthesis of the environmentally sensitive fluorophore 6-DMN on a gram scale with a shorter time, fewer steps and less waste disposal, and without the utilization of toxic transition metals. The present experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.