144128-71-2

Basic information

• Product Name: 5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE
• Synonyms: 5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE;5-(3-broMophenyl)-1,3-Cyclohexanedione;1,3-Cyclohexanedione, 5-(3-broMophenyl)-;5-(3-Bromophenyl)-3-hydroxycyclohex-2-ene-1-one
• CAS NO: 144128-71-2
• Molecular Formula: C₁₂H₁₁BrO₂
• Molecular Weight: 267.12
• Product Categories: Halides;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 144128-71-2.mol

Chemical Properties

• Boiling Point: 399.37 °C at 760 mmHg
• Flash Point: 138.694 °C
• Appearance: /
• Density: 1.486 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.583
• PKA: 4.89±0.20(Predicted)
• CAS DataBase Reference: 5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE(144128-71-2)
• EPA Substance Registry System: 5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE(144128-71-2)

Safety Data

• Hazardous Substances Data: 144128-71-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE is used as a reagent in organic synthesis for its ability to participate in a variety of chemical reactions. Its presence in the synthesis process can lead to the formation of new compounds with different properties and applications.
Used in Chemical Reactions:
In the chemical industry, 5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE is employed as a reagent in various chemical reactions. Its unique structure allows it to react with other compounds, facilitating the production of desired products in chemical processes.
Used in Pharmaceutical Industry:
5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE is used as an intermediate in the synthesis of pharmaceutical compounds. Its involvement in the production of drugs can contribute to the development of new medications with specific therapeutic effects.
Used in Research and Development:
In the field of research and development, 5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE is utilized as a compound for studying its properties and potential applications. Scientists and researchers explore its reactivity, stability, and other characteristics to understand its behavior in different chemical environments.
Used in Analytical Chemistry:
5-(3-BROMO-PHENYL)-CCYCLOHEXANE-1,3-DIONE is employed as a reference compound in analytical chemistry. It can be used to calibrate instruments, validate analytical methods, and ensure the accuracy of measurements in various chemical analyses.

InChI:InChI=1/C12H11BrO2/c13-10-3-1-2-8(4-10)9-5-11(14)7-12(15)6-9/h1-4,9H,5-7H2

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 26891-02-1 4-(3-Bromphenyl)-3-buten-2-on 
• 105-53-3 diethyl malonate 

Downstream Products

• 144128-92-7 3-[3-Bromophenyl]-7-chloro-3,4-dihydro-10-hydroxy-1,9(2H,10H)-acridinedione 

Relevant articles and documents

Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC50 of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS.

PROCESS FOR THE PRODUCTION OF OPTICALLY ACTIVE CYCLIC ENAMINONE DERIVATIVES

A process for the production of optically active cyclic enaminone derivatives characterized by aminating one of the carbonyl groups of a cyclic 1,3-diketone derivative having a symmetry plane to obtain an optically isomeric mixture of chiral cyclic enamin

Synthesis and Antimalarial Properties of 1-Imino Derivatives of 7-Chloro-3-substituted-3,4-dihydro-1,9(2H,10H)-acridinediones and Related Structures

To improve upon the activity and properties of the 3-aryl-7-chloro-3,4-dihydro-1,9(2H,10H)-acridinediones, a variety of 1-imino derivatives (3) were prepared and shown to be highly active antimalarial agents in both rodents and primates.Among structural modifications prepared, including N10-alkyl and C2-substituted analogs, removal of the C9 oxygen, and introduction of an imino side chain at C9, the imines of the N10-H acridinediones were the most active compounds obtained.The imino derivative of7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione (9aa) proved to be highly active in advanced studies in primates.