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
• Article Data: 19

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

Description

(2E)-3-(2-bromophenyl)acryloyl chloride is a chemical compound that features an acryloyl chloride group attached to a 2-bromophenyl group. (2E)-3-(2-bromophenyl)acryloyl chloride is known for its reactivity and is widely utilized as a building block in the synthesis of a variety of organic compounds, such as pharmaceuticals, agrochemicals, and functional materials. The acryloyl chloride moiety is particularly noted for its ability to participate in nucleophilic addition and substitution reactions, while the bromine atom in the 2-bromophenyl group endows the compound with distinct chemical and physical characteristics. These attributes render (2E)-3-(2-bromophenyl)acryloyl chloride a valuable and versatile component in organic chemistry.

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

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

Downstream Products

• 1637568-97-8 2-(2-bromophenyl)-5,6,7-trimethoxy-4H-chromen-4-one 
• 1637568-98-9 2-(2-bromophenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one 
• 1637569-01-7 2-(2-bromophenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one 
• 1637569-03-9 2-(2-bromophenyl)-5,6,7-trihydroxy-4H-chromen-4-one 
• 1637568-96-7 C₁₈H₁₇BrO₅ 
• 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, 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

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.

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.