851664-10-3

Basic information

• Product Name: (2E)-3-(2-bromophenyl)acryloyl chloride
• Synonyms: (2E)-3-(2-bromophenyl)acryloyl chloride;2-propenoyl chloride, 3-(2-bromophenyl)-, (2E)-;(E)-3-(2-bromophenyl)acryloyl chloride;(E)-3-(2-bromophenyl)prop-2-enoyl chloride
• CAS NO: 851664-10-3
• Molecular Formula: C9H6BrClO
• Molecular Weight: 245.50034
• Mol File: 851664-10-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-3-(2-bromophenyl)acryloyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(2-bromophenyl)acryloyl chloride(851664-10-3)
• EPA Substance Registry System: (2E)-3-(2-bromophenyl)acryloyl chloride(851664-10-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 851664-10-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(2E)-3-(2-bromophenyl)acryloyl chloride is used as a key intermediate for the synthesis of pharmaceutical compounds. Its reactivity allows for the creation of new chemical entities that can possess therapeutic properties, contributing to the development of novel drugs.
Used in Agrochemical Production:
In the agrochemical industry, (2E)-3-(2-bromophenyl)acryloyl chloride is employed as a building block for the synthesis of various agrochemicals. Its unique structure and reactivity enable the production of compounds that can be used in crop protection and other agricultural applications.
Used in the Synthesis of Functional Materials:
(2E)-3-(2-bromophenyl)acryloyl chloride is utilized as a precursor in the development of functional materials. These materials can have specialized properties, such as conductivity, magnetism, or specific binding capabilities, and are used in various high-tech applications.
Used in Organic Synthesis Research:
As a versatile chemical building block, (2E)-3-(2-bromophenyl)acryloyl chloride is also used in academic and industrial research settings for organic synthesis. It serves as a model compound to study reaction mechanisms, develop new synthetic methodologies, and explore the potential of novel chemical reactions.

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 7345-79-1 2-bromocinnamic acid 
• 66223-53-8 trans-2-bromocinnamaldehyde 
• 7345-79-1 2-bromocinnamic acid 

Downstream Products

• 1637568-96-7 C₁₈H₁₇BrO₅ 
• 1637569-03-9 2-(2-bromophenyl)-5,6,7-trihydroxy-4H-chromen-4-one 
• 1637569-01-7 2-(2-bromophenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one 
• 1637568-98-9 2-(2-bromophenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one 
• 1637568-97-8 2-(2-bromophenyl)-5,6,7-trimethoxy-4H-chromen-4-one 
• 1619972-36-9 (4β,8β)-4-(acetyloxy)-12,13-epoxytrichothec-9-en-8-yl (2E)-3-(2-bromine-phenylprop)-2-enoate 

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.

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.

Design, Synthesis, Structure-Activity Relationship, Molecular Docking, and Herbicidal Evaluation of 2-Cinnamoyl-3-Hydroxycyclohex-2-en-1-one Derivatives as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

Cinnamic acid, isolated from cinnamon bark, is a natural product with excellent bioactivity, and it effectively binds with cyclohexanedione to form novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors. According to the active sub-structure combinat

1,4-Palladium Shift/C(sp3)-H Activation Strategy for the Remote Construction of Five-Membered Rings

1,n-Metal shift is an elegant alternative approach enabling the functionalization of remote C-H bonds from simple precursors. In this work, we report a novel and simple Pd0-catalyzed domino reaction involving 1,4-palladium shift and C(sp3)-H activation and leading to (fused) five-membered rings. This method allowed access to a broad range of valuable arylidene γ-lactams and indanones and was applied to the formal synthesis of (-)-pyrrolam.

Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection

A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa Mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.

Identification and Structure-Activity Relationships of Novel Compounds that Potentiate the Activities of Antibiotics in Escherichia coli

In Gram-negative bacteria, efflux pumps are able to prevent effective cellular concentrations from being achieved for a number of antibiotics. Small molecule adjuvants that act as efflux pump inhibitors (EPIs) have the potential to reinvigorate existing antibiotics that are currently ineffective due to efflux mechanisms. Through a combination of rigorous experimental screening and in silico virtual screening, we recently identified novel classes of EPIs that interact with the membrane fusion protein AcrA, a critical component of the AcrAB-TolC efflux pump in Escherichia coli. Herein, we present initial optimization efforts and structure-activity relationships around one of those previously described hits, NSC 60339 (1). From these efforts we identified two compounds, SLUPP-225 (17h) and SLUPP-417 (17o), which demonstrate favorable properties as potential EPIs in E. coli cells including the ability to penetrate the outer membrane, improved inhibition of efflux relative to 1, and potentiation of the activity of novobiocin and erythromycin.

Solid state conformations of α,β-unsaturated hydroxamates derived from the ‘chiral Weinreb amide’ auxiliary (S)-N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine

α,β-Unsaturated hydroxamates derived from the ‘chiral Weinreb amide’ auxiliary (S)-N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine consistently adopt a defined conformation and undergo highly diastereoselective conjugate addition reactions with lithium a

Silver-catalyzed radical tandem cyclization for the synthesis of 3,4-disubstituted dihydroquinolin-2(1 H)-ones

A silver-catalyzed tandem decarboxylative radical addition/cyclization of N-arylcinnamamides with aliphatic carboxylic acids is reported. This method affords a novel and straightforward route to various 3,4-disubstituted dihydroquinolin-2(1H)-ones in aque

Synthesis and anti-influenza activities of novel baicalein analogs

A series of novel flavones derivatives were synthesized based on modification of the active ingredients of a traditional Chinese medicine Scutellaria baicalensis GEORGI and screened for anti-influenza activity. The synthetic baicalein (flavone) analogs, especially with the B-rings substituted with bromine atoms, were much more potent than oseltamivir or ribavirin against H1N1 Tamiflu-resistant (H1N1 TR) virus and usually with more favorable selectivity. The most promising were 5b, 5c, 6b and 6c, all displaying an 50% effective concentration (EC50) at around 4.0-4.5 μM, and a selective index (SI=50% cytotoxic concentration (CC50)/EC 50)>70. For seasonal H3N2-infected influenza virus, both 5a and 5b with SI >17.3 indicated superior to ribavirin. The flavonoids having both not-naturally-occurring bromo-substituted B-rings and appropriate hydroxyls positioning on the A-rings might be critical in determining the activity and selectivity against H1N1-Tamiflu-resistant infected influenza viruses.

The synthesis of 3,4-disubstituted dihydroquinolin-2(1H)-one under metal-free conditions in aqueous solution

A novel route toward 3,4-disubstituted dihydroquinolin-2(1H )-ones via radical process has been developed in aqueous solution without metals. This method offers a new and simple route for the synthesis of skeleton of dihydroquinolin-2(1H )-one in one step