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
• Article Data: 3

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

General Description

5-(3-Bromo-phenyl)-cyclohexane-1,3-dione is a chemical compound with a molecular formula C12H13BrO2. It is also known by the common name 3-Bromophenylcyclohexane-1,3-dione. 5-(3-BROMO-PHENYL)-CYCLOHEXANE-1,3-DIONE is a member of the class of cyclohexane-1,3-diones and contains a bromophenyl group. It is commonly used as a reagent in organic synthesis and chemical reactions. Its specific properties and applications may vary based on the chemical reactions and processes in which it is involved.

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

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

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.

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.