6323-02-0

Basic information

• Product Name: 2,5-bis(diethylamino)cyclohexa-2,5-diene-1,4-dione
• CAS NO: 6323-02-0
• Molecular Formula: C₁₄H₂₂N₂O₂
• Molecular Weight: 250.3367
• Mol File: 6323-02-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 351.9°C at 760 mmHg
• Flash Point: 137.6°C
• Density: 1.06g/cm³
• Vapor Pressure: 3.98E-05mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 2,5-bis(diethylamino)cyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(diethylamino)cyclohexa-2,5-diene-1,4-dione(6323-02-0)
• EPA Substance Registry System: 2,5-bis(diethylamino)cyclohexa-2,5-diene-1,4-dione(6323-02-0)

Safety Data

• Hazardous Substances Data: 6323-02-0(Hazardous Substances Data)

Usage

Class

Cyclohexanediones

Contains

Two diethylamino groups

Potential applications

Medicine and pharmaceuticals

Studied for

Potential anti-androgen and anti-cancer properties

Investigated as treatment for

Prostate cancer and COVID-19

Potential ability

Inhibiting the activity of androgen receptors and having anti-inflammatory effects

Possible therapeutic potential for

Hormone-dependent cancers and autoimmune diseases

Need for further research

To fully understand the potential uses and effects of this chemical compound.

Upstream product

• 109-89-7 diethylamine 
• 106-51-4 p-benzoquinone 
• 18358-64-0 N,N'-diphenyl-p-benzoquinone di-imine N,N'-dioxide 
• 83925-66-0 N,N'-bis(4-methoxyphenyl)-p-benzoquinone di-imine N,N'-dioxide 

Downstream Products

• 172216-15-8 2,5-Bis(N,N-diethylamino)-4-<(trimethylsilyl)ethynyl>-1-(butyloxy)benzene 
• 172216-16-9 2,5-Bis(N,N-diethylamino)-4-ethynyl-1-(butyloxy)benzene 
• 172216-14-7 2,5-Bis(N,N-diethylamino)-4-<(trimethylsilyl)ethynyl>phenol 
• 7471-00-3 1,4-diacetoxy-2,5-bis-diethylamino-benzene 

Relevant articles and documents

A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26

The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation. Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)2 and Mn(OAc)3?2 H2O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented.

Probing Delocalization across Alkyne-Containing Linkages: Synthesis and Cyclic Voltammetry of Bridged Phenylenediamines

This paper presents the synthesis of N,N,N',N'-tetraethyl-1,4-phenylenediamines bridged by ethynyl-phenyl-ethynyl and diethynyl linkages.These compounds are of interest to determine if the N,N,N',N'-tetraethyl-1,4-phenylenediamines exhibit delocalized mixed oxidation states when oxidized electrochemically. 1-Butoxy-2,5-bis(N,N-diethylamino)-4-ethynylbenzene was a key intermediate, and nucleophilic addition of lithium (trimethylsilyl)acetylide to 2,5-bis(N,N-diethylamino)-1,4-benzoquinone provided an efficient synthesis of this compound.This intermediate was then assembled into the redox assemblies of interest in high yield by use of palladium-catalyzed cross-coupling and copper-catalyzed oxidative homo-coupling protocols.Cyclic voltammetry of these compounds indicate that the N,N,N',N'-tetraethyl-1,4-phenylenediamine redox units behave independently and that the interactions are principally electrostatic.As a result, we conclude that the electrochemically generated radical cations and dications are highly localized.