37859-24-8

Basic information

• Product Name: 4-Bromophenylacetyl chloride
• Synonyms: 4-BROMOPHENYLACETIC ACID CHLORIDE;(4-BROMO-PHENYL)-ACETYL CHLORIDE;2-(4-bromophenyl)ethanoyl chloride;(4-Bromo-phenyl)-acetyl chloride ,95%;Benzeneacetyl chloride,4-bromo-
• CAS NO: 37859-24-8
• Molecular Formula: C₈H₆BrClO
• Molecular Weight: 233.49
• Product Categories: pharmacetical
• Mol File: 37859-24-8.mol

Chemical Properties

• Boiling Point: 180-185°C/10mm
• Flash Point: >110℃
• Appearance: /
• Density: 1.573 g/mL at 25 °C
• Vapor Pressure: 0.00296mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-Bromophenylacetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromophenylacetyl chloride(37859-24-8)
• EPA Substance Registry System: 4-Bromophenylacetyl chloride(37859-24-8)

Safety Data

• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 26-36/37/39-45
• RIDADR: 3265
• WGK Germany: 3
• Hazardous Substances Data: 37859-24-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromophenylacetyl chloride is used as an intermediate in the synthesis of pharmaceuticals for its ability to introduce the 4-bromophenylacetyl group into target molecules, which can enhance the pharmacological properties of the resulting compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Bromophenylacetyl chloride is utilized as a precursor in the production of various agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Organic Synthesis:
4-Bromophenylacetyl chloride is employed as a versatile reagent in organic synthesis, where it serves to introduce the 4-bromophenylacetyl group into a wide range of organic molecules, facilitating the creation of new compounds with potential applications in various fields.
Used in Drug Development:
As a building block in drug development, 4-Bromophenylacetyl chloride is instrumental in the design and synthesis of new drugs and bioactive compounds, potentially leading to advancements in medical treatments and therapies.

InChI:InChI=1/C8H6BrClO/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2

Upstream product

• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 1197-55-3 4-aminophenylacetic acid 
• 7719-09-7 thionyl chloride 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 

Downstream Products

• 67205-73-6 2-(4-bromophenyl)-1-(4-methoxyphenyl)-1-ethanone 
• 112030-35-0 3-(4-bromophenyl)-4-methyl-2H-chromen-2-one 
• 64267-81-8 (4-Bromo-phenyl)-acetic acid N'-methyl-N'-phenyl-hydrazide 
• 22421-88-1 4-bromobenzyl phenyl ketone 
• 177846-87-6 ethyl 2-(4-bromophenylacetyl)-3-oxo-4-phenylbutanoate 
• 177846-64-9 ethyl 2-(4-bromophenylacetyl)-3-oxo-3-phenylpropanoate 
• 177846-26-3 methyl 2-(4-bromophenylacetyl)-3-oxobutanoate 
• 177846-59-2 ethyl 2-(4-bromophenylacetyl)-3-oxohexanoate 
• 232953-61-6 3-(2-(4-bromophenyl)acetyl)oxazolidin-2-one 
• 232953-62-7 3-[2-(4-bromophenyl)acetyl]-4-isopropyloxazolidin-2-one 
• 189626-02-6 ethyl 4-(p-bromophenyl)-2-methyl-2,3-butadienoate 

Relevant articles and documents

A novel complexity-to-diversity strategy for the diversity-oriented synthesis of structurally diverse and complex macrocycles from quinine

Recent years have witnessed a global decline in the productivity and advancement of the pharmaceutical industry. A major contributing factor to this is the downturn in drug discovery successes. This can be attributed to the lack of structural (particularly scaffold) diversity and structural complexity exhibited by current small molecule screening collections. Macrocycles have been shown to exhibit a diverse range of biological properties, with over 100 natural product-derived examples currently marketed as FDA-approved drugs. Despite this, synthetic macrocycles are widely considered to be a poorly explored structural class within drug discovery, which can be attributed to their synthetic intractability. Herein we describe a novel complexity-to-diversity strategy for the diversity-oriented synthesis of novel, structurally complex and diverse macrocyclic scaffolds from natural product starting materials. This approach exploits the inherent structural (including functional) and stereochemical complexity of natural products in order to rapidly generate diversity and complexity. Readily-accessible natural product-derived intermediates serve as structural templates which can be divergently functionalized with different building blocks to generate a diverse range of acyclic precursors. Subsequent macrocyclisation then furnishes compounds that are each based around a distinct molecular scaffold. Thus, high levels of library scaffold diversity can be rapidly achieved. In this proof-of-concept study, the natural product quinine was used as the foundation for library synthesis, and six novel structurally diverse, highly complex and functionalized macrocycles were generated.

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

MODULATORS OF HSD17B13 AND METHODS OF USE THEREOF

The disclosure relates to compounds and pharmaceutical compositions capable of modulating the hydroxysteroid 17-beta dehydrogenase (HSD17B) family member proteins including inhibiting the HSD17B member proteins, e.g. HSD17B13. The disclosure further relates to methods of treating liver diseases, disorders, or conditions with the compounds and pharmaceutical compositions disclosed herein, in which the HSD17B family member protein plays a role.

Identification of BR102910 as a selective fibroblast activation protein (FAP) inhibitor

Fibroblast activation protein (FAP) belongs to the family of prolyl-specific serine proteases and displays both exopeptidase and endopeptidase activities. FAP expression is undetectable in most normal adult tissues, but is greatly upregulated in sites of tissue remodeling, which include fibrosis, inflammation and cancer. Due to its restricted expression pattern and dual enzymatic activities, FAP inhibition is investigated as a therapeutic option for several diseases. In the present study, we described the structure–activity relationship of several synthesized compounds against DPPIV and prolyl oligopeptidase (PREP). In particular, BR102910 (compound 24) showed nanomolar potency and high selectivity. Moreover, the in vivo FAP inhibition study of BR102910 (compound 24) using C57BL/6J mice demonstrated exceptional profiles and satisfactory FAP inhibition efficacy. Based on excellent in vitro and in vivo profiles, the potential of BR102910 (compound 24) as a lead candidate for the treatment of type 2 diabetes is considered.

The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.

A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones

Chiral cyclopropane rings are key pharmacophores in pharmaceuticals and bioactive natural products, making libraries of these building blocks a valuable resource for drug discovery and development campaigns. Here, we report the development of a chemoenzymatic strategy for the stereoselective assembly and structural diversification of cyclopropyl ketones, a highly versatile yet underexploited class of functionalized cyclopropanes. An engineered variant of sperm whale myoglobin is shown to enable the highly diastereo- and enantioselective construction of these molecules via olefin cyclopropanation in the presence of a diazoketone carbene donor reagent. This biocatalyst offers a remarkably broad substrate scope, catalyzing this reaction with high stereoselectivity across a variety of vinylarene substrates as well as a range of different α-aryl and α-alkyl diazoketone derivatives. Chemical transformation of these enzymatic products enables further diversification of these molecules to yield a collection of structurally diverse cyclopropane-containing scaffolds in enantiopure form, including core motifs found in drugs and natural products as well as novel structures. This work illustrates the power of combining abiological biocatalysis with chemoenzymatic synthesis for generating collections of optically active scaffolds of high value for medicinal chemistry and drug discovery.

Design, synthesis and biological evaluation of novel pyrrolidone-based derivatives as potent p53-MDM2 inhibitors

Inhibition of the interactions of the tumor suppressor protein p53 with its negative regulators MDM2 in vitro and in vivo, representing a valuable therapeutic strategy for cancer treatment. The natural product chalcone exhibited moderate inhibitory activity against MDM2, thus based on the binding mode between chalcone and MDM2, a hit unsaturated pyrrolidone scaffold was obtained through virtual screening. Several unsaturated pyrrolidone derivatives were synthesized and biological evaluated. As a result, because the three critical hydrophobic pockets of MDM2 were occupied by the substituted-phenyl linked at the pyrrolidone fragment, compound 4 h demonstrated good binding affinity with the MDM2. Additionally, compound 4 h also showed excellent antitumor activity and selectivity, and no cytotoxicity against normal cells in vitro. The further antitumor mechanism studies were indicated that compound 4 h could successfully induce the activation of p53 and corresponding downstream p21 proteins, thus successfully causing HCT116 cell cycle arrest in the G1/M phase and apoptosis. Thus, the novel unsaturated pyrrolidone p53-MDM2 inhibitors could be developed as novel antitumor agents.

Quantitative activity-activity relationship (QAAR) driven design to develop hydroxamate derivatives of pentanoic acids as selective HDAC8 inhibitors: synthesis, biological evaluation and binding mode of interaction studies

Histone deacetylase 8 (HDAC8) has been implicated as a potential drug target of many diseases including cancer. HDAC8 isoform selectivity over other class-I HDACs is a major concern nowadays. In this work, a series of pentanoic acid based hydroxamates wit

Visible-Light-Mediated Strategies for the Preparation of Oxime Ethers Derived from O-H Insertions of Oximes into Aryldiazoacetates

Two visible-light-mediated O-H insertion protocols involving oximes and aryldiazoacetates leading to different products depending on the solvent employed are reported. In DCM, direct O-H insertion takes place. In THF, there is the additional incorporation of the ring-opened form of this solvent into the structure of the product. These metal-free protocols are mild and tolerant to air and moisture. The preparation of an acaricide has been developed as an example of synthetic application.

Visible-Light-Mediated Strategies to Assemble Alkyl 2-Carboxylate-2,3,3-Trisubstituted β-Lactams and 5-Alkoxy-2,2,4-Trisubstituted Furan-3(2H)-ones Using Aryldiazoacetates and Aryldiazoketones

Two new visible-light-mediated strategies are described starting from aryldiazoacetates. The first approach describes their reaction with azides to afford the corresponding imines, and then reaction with aryldiazoketones produces alkyl 2-carboxylate-2,3,3