3421-08-7

Basic information

• Product Name: 2,5-Bis(phenylamino)-1,4-benzoquinone
• Synonyms: 2,5-Bis(phenylamino)-1,4-benzoquinone;2,5-Bis(phenylamino)-2,5-cyclohexadiene-1,4-dione;2,5-Bis(phenylamino)-p-benzoquinone;C.I.56000;Helindon Yellow CA;Helindon Yellow CAK
• CAS NO: 3421-08-7
• Molecular Formula: C₁₈H₁₄N₂O₂
• Molecular Weight: 290.32
• Mol File: 3421-08-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 300 °C (decomp)
• Boiling Point: 471.9°C at 760 mmHg
• Flash Point: 175.8°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 4.46E-09mmHg at 25°C
• Refractive Index: 1.741
• PKA: -1.60±0.20(Predicted)
• CAS DataBase Reference: 2,5-Bis(phenylamino)-1,4-benzoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Bis(phenylamino)-1,4-benzoquinone(3421-08-7)
• EPA Substance Registry System: 2,5-Bis(phenylamino)-1,4-benzoquinone(3421-08-7)

Safety Data

• Hazardous Substances Data: 3421-08-7(Hazardous Substances Data)

Usage

General Description

2,5-Bis(phenylamino)-1,4-benzoquinone, also known as PBQ, is a chemical compound with the molecular formula C18H14N2O2. It is a dark red solid that is commonly used as an electron transport material in organic electronic devices such as organic light-emitting diodes (OLEDs) and solar cells. PBQ is known for its high electron mobility and excellent stability, making it a popular choice for improving the efficiency and durability of these devices. Additionally, PBQ has been studied for its potential applications in organic electronics and has shown promising results in enhancing the performance of various optoelectronic devices.

InChI:InChI=1/C18H14N2O2/c21-17-12-16(20-14-9-5-2-6-10-14)18(22)11-15(17)19-13-7-3-1-4-8-13/h1-12,19-20H

Upstream product

• 695-99-8 2-Chloro-1,4-benzoquinone 
• 542-14-3 aniline acetate 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 62-53-3 aniline 
• 64-17-5 ethanol 
• 106-51-4 p-benzoquinone 
• 88-75-5 2-hydroxynitrobenzene 
• 64-19-7 acetic acid 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 542-11-0 aniline hydrobromide 
• 4916-29-4 dimethyl (Z)-N-(phenyl)aminofumarate 
• 19788-30-8 4-nitroso-N-ethylaniline 
• 10595-51-4 4-nitroso-N-methylaniline 
• 156-10-5 p-nitrosodiphenylamine 

Downstream Products

• 121565-48-8 2-anilino-hydroquinone 
• 615-94-1 2,5-dihydroxy-1,4-benzoquinone 
• 4435-12-5 azophenin 

Relevant articles and documents

Synthesis, electrochemical and anti-microbial study of 2,5-diamino benzoquinones

Fifteen symmetric and unsymmetric 2,5-diamino benzoquinones have been synthesized and their electrochemical activity was studied by cyclic voltammetry. Presence of electron donating substituent like amino group found to shift the half wave potential towar

Development of quinone analogues as dynamin GTPase inhibitors

Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4- benzoquinone 1 as a 273 ± 106 μM inhibitor. In silico lead optimization and focused library-led synthesis resulted in the development of four discrete benzoquinone/naphthoquinone based compound libraries comprising 54 compounds in total. Sixteen analogues were more potent than lead 1, with 2,5-bis-(4-hydroxyanilino)-1,4-benzoquinone (45) and 2,5-bis(4-carboxyanilino)- 1,4-benzoquinone (49) the most active with IC50 values of 11.1 ± 3.6 and 10.6 ± 1.6 μM respectively. Molecular modelling suggested a number of hydrogen bonding and hydrophobic interactions were involved in stabilization of 49 within the dynI GTP binding site. Six of the most active inhibitors were evaluated for potential inhibition of clathrin-mediated endocytosis (CME). Quinone 45 was the most effective CME inhibitor with an IC50(CME) of 36 ± 16 μM.

Electronic effects of ligand substitution on spin crossover in a series of diiminoquinonoid-bridged FeII2 complexes

A series of four isostructural FeII2 complexes, [(TPyA)2Fe2(XL)]2+ (TPyA = tris(2-pyridylmethyl)amine; XL2-= doubly deprotonated form of 3,6-disubstituted-2,5-dianilin