14659-11-1

Basic information

• Product Name: 5-(4-Bromo-phenyl)-[1,2]dithiole-3-thione
• Synonyms: 5-(4-Bromo-phenyl)-[1,2]dithiole-3-thione;5-(4-Bromophenyl)dithiole-3-thione
• CAS NO: 14659-11-1
• Molecular Formula: C₉H₅BrS₃
• Molecular Weight: 289.235
• Mol File: 14659-11-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 129 °C
• Boiling Point: 404.7 °C at 760 mmHg
• Flash Point: 198.6 °C
• Appearance: /
• Density: 1.8 g/cm³
• Vapor Pressure: 2.17E-06mmHg at 25°C
• Refractive Index: 1.81
• CAS DataBase Reference: 5-(4-Bromo-phenyl)-[1,2]dithiole-3-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-Bromo-phenyl)-[1,2]dithiole-3-thione(14659-11-1)
• EPA Substance Registry System: 5-(4-Bromo-phenyl)-[1,2]dithiole-3-thione(14659-11-1)

Safety Data

• Hazardous Substances Data: 14659-11-1(Hazardous Substances Data)

Usage

Properties

1. Molecular formula: C9H5BrS2
2. Dithiolethione derivative
3. Contains a 5-(4-bromo-phenyl) group attached to the dithiole-3-thione core
4. Potential biological activities: anticancer, antioxidant, and anti-inflammatory
5. Potential applications in medicinal chemistry and drug development

Specific content

Chemical compound
Dithiolethione derivative
5-(4-bromo-phenyl) group

Potential biological activities

anticancer, antioxidant, anti-inflammatory
Potential applications in medicinal chemistry and drug development

InChI:InChI=1/C9H5BrS3/c10-7-3-1-6(2-4-7)8-5-9(11)13-12-8/h1-5H

Upstream product

• 2294-43-1 1-allyl-4-bromo-benzene 
• 57367-05-2 1-(4-bromophenyl)-3,3-dimercapto-2-propen-1-one 
• 26510-95-2 ethyl 4-Bromobenzoylacetate 
• 586-76-5 4-Bromobenzoic acid 
• 82892-00-0 N-(4-bromobenzoyl)imidazole 
• 39580-38-6 1-(4-bromophenyl)-3,3-bis(methylthio)prop-2-en-1-one 

Downstream Products

• 152547-70-1 2-[2-(4-Bromo-phenyl)-2-oxo-eth-(Z)-ylidene]-5-diethoxymethyl-[1,3]dithiole-4-carbaldehyde 

Relevant articles and documents

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

N2S2 tetradentate ligands for soft cationic species: preparation of new ligands of potential interest in nuclear medicine

The synthesis of N2S2 tetradentate ligands of the bis-(enaminothioester) type was carried out starting from 3-(methylthio)-3H-1,2-dithiolylium iodides and diamines.The title compounds, which are potential ligands for soft cationic species, can be obtained from 1,3-diaminopropan-2-ol and subsequently modified into the dissymmetrical succinic acid ester of the ligand and N-hydroxysuccinimide.The appendage of such a linking group on the chelating structure should allow further grafting to monoclonal antibodies in view of potential applications in nuclear medicine. 3H-1,2-dithiole-3-thione / 1,3-diaminopropan-2-ol / bis-(enaminothioester) / N2S2 tetradentate ligand / N-hydroxysuccinimidyl ester