81559-89-9

Basic information

• Product Name: 2,6-DICHLOROBENZYLIDENEACETONE
• Synonyms: 2,6-DICHLOROBENZYLIDENEACETONE;4-(2,6-DICHLOROPHENYL)BUT-3-EN-2-ONE;1-(2,6-DICHLOROPHENYL)BUT-1-EN-3-ONE
• CAS NO: 81559-89-9
• Molecular Formula: C₁₀H₈Cl₂O
• Molecular Weight: 215.08
• Mol File: 81559-89-9.mol

Chemical Properties

• Boiling Point: 136 °C
• Flash Point: 135-136°C/2mm
• Appearance: /
• Refractive Index: 1.5920
• CAS DataBase Reference: 2,6-DICHLOROBENZYLIDENEACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DICHLOROBENZYLIDENEACETONE(81559-89-9)
• EPA Substance Registry System: 2,6-DICHLOROBENZYLIDENEACETONE(81559-89-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 81559-89-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,6-Dichlorobenzylideneacetone is used as a precursor in the synthesis of chiral organic compounds for the production of pharmaceuticals and agrochemicals. Its unique structure allows for the creation of enantiomerically pure compounds, which are crucial in the development of effective and safe drugs and pesticides.
Used in Organic Electronic Devices:
DCBA has been studied for its potential use in organic electronic devices due to its electronic properties. Its application in this field could contribute to the development of advanced electronic components and systems with improved performance and efficiency.
Used as a Fluorescent Probe:
2,6-Dichlorobenzylideneacetone is utilized as a fluorescent probe for detecting various metal ions. Its ability to emit fluorescence upon interaction with metal ions makes it a valuable tool in analytical chemistry and environmental monitoring for the detection and quantification of metal contaminants.

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 55579-74-3 5-(2,6-dichlorophenyl)cyclohexane-1,3-dione 
• 144128-39-2 7-Chloro-3-(2,6-dichloro-phenyl)-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one 
• 55579-52-7 7-chloro-3-(2,6-dichlorophenyl)-3,4-dihydro-10-hydroxy-1,9(2H,10H)-acridinedione 

Relevant articles and documents

Dehydrozingerone derivative and preparation method and application thereof

The invention provides a dehydrozingerone derivative as shown in the description. R-R are each independently selected from hydrogen or halogen or a nitro group or an alkyl group or a substitutedalkoxy group or an alkoxy group or a hydroxyl group; the substituent in the substituted alkoxy group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; R and R areeach independently selected from hydrogen or halogen or nitrogen-containing heterocycle; R is selected from an alkyl group or an alkoxy group or a substituted alkoxy group; the substituent in thesubstituted alkyl group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; X is selected from a hetero atom or a hydroxylamine group. The dehydrozingerone derivative hasbroad-spectrum activity against plant pathogenic fungi and bacteria, and has certain nematicidal activity, and is a lead compound with the broad biological activity.

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.

Organocatalyst-mediated aldolrobinson cascade reactions: A convenient synthesis of substituted cyclohex-2-enones

A convenient organocatalytic process for the chemoselective synthesis of substituted cyclohex-2-enones was developed. The cascade reaction involves a remarkable Michael addition of an acyclic ketone-based enamine onto unmodified enones. The enamine-mediated aldolRobinson cascade reactions of aromatic and aliphatic aldehydes with acetone produced substituted cyclohex-2-enones in moderate to high yields under mild reaction conditions.

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.