2474-72-8

Basic information

• Product Name: 2-hydroxy-1,4-benzoquinone
• Synonyms: 2-hydroxy-1,4-benzoquinone
• CAS NO: 2474-72-8
• Molecular Formula: C₆H₄O₃
• Molecular Weight: 124.09
• Mol File: 2474-72-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 128 °C(Solv: benzene (71-43-2))
• Boiling Point: 247.8°Cat760mmHg
• Flash Point: 118°C
• Appearance: /
• Density: 1.531g/cm³
• Vapor Pressure: 0.00407mmHg at 25°C
• Refractive Index: 1.627
• PKA: 2.90±0.30(Predicted)
• CAS DataBase Reference: 2-hydroxy-1,4-benzoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-1,4-benzoquinone(2474-72-8)
• EPA Substance Registry System: 2-hydroxy-1,4-benzoquinone(2474-72-8)

Safety Data

• Hazardous Substances Data: 2474-72-8(Hazardous Substances Data)

Usage

Definition

ChEBI: The simplest member of the class of 2-hydroxy-1,4-benzoquinones, that is 1,4-benzoquinone in which a single hydrogen is replaced by a hydroxy group.

InChI:InChI=1/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9H

Upstream product

• 533-73-3 1,2,4-Trihydroxybenzene 
• 106-51-4 p-benzoquinone 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 108-95-2 phenol 
• 371-41-5 4-Fluorophenol 
• 2138-22-9 4-chloro-1,2-benzenediol 
• 106-48-9 4-chloro-phenol 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 106-46-7 para-dichlorobenzene 
• 120-80-9 benzene-1,2-diol 
• 123-31-9 hydroquinone 
• 71-43-2 benzene 
• 94-26-8 4-hydroxybenzoic acid, butyl ester 

Downstream Products

• 550-82-3 resazurin 
• 641-30-5 aposafranone 
• 531-47-5 5,12-dihydro-5,7,12,14-tetraazapentacene 
• 3421-08-7 2,5-bis(phenylamino)-1,4-benzoquinone 
• 124251-44-1 5-anilino-2-hydroxy-1,4-benzoquinone 
• 4190-95-8 2-hydroxyphenazine 
• 533-73-3 1,2,4-Trihydroxybenzene 

Relevant articles and documents

Phototransformation of resorcinol induced by excitation of nitrite and nitrate ions. II: nitrate ions

The excitation of nitrate ions in an aqueous solution of resorcinol (I) at pH = 5.5-6.5, leads to a mixture of 1,2,3-trihydroxybenzene (II), 1,2,4-trihydroxybenzene (III), 4-nitrosoresorcinol (V) and 4-nitroresorcinol (VII). A secondary formation of 2, 4-dinitrosoresorcinol (VI) was also detected.

Kinetic studies of hydroxyquinone formation from water soluble benzoquinones

The kinetics and mechanisms of the redox reactions between hydrogen peroxide and 1,4-benzoquinone, 2-methyl-1,4-benzoquinone, 2,6-dimethyl-1,4- benzoquinone, 2-chloro-1,4-benzoquinone and 2,6-dichloro-1,4-benzoquinone were studied in aqueous media using spectrophotometric monitoring. The formation and decay of a hydroxylated 1,4-benzoquinone was detected. The formation of the intermediate was first order with respect to the parent 1,4-benzoquinone and hydrogen peroxide, whereas inverse first order dependence was revealed with respect to the hydrogen ion. The decomposition reaction had two parallel pathways: one was first order with respect to the intermediate, while the other showed second-order dependence. The values of the rate constant measured for the formation step were successfully correlated with both the redox potentials of the substituted quinone-hydroquinone systems and the pKa values of the hydroxylated quinone derivatives. Therefore, electronic effects govern the reactivity of the quinones in this process. NMR and GC-MS measurements were carried out to identify the products in the system. Quantum mechanical calculations were also carried out in these systems.

Two-Dimensional Layered Zinc Silicate Nanosheets with Excellent Photocatalytic Performance for Organic Pollutant Degradation and CO2 Conversion

Two-dimensional (2D) photocatalysts are highly attractive for their great potential in environmental remediation and energy conversion. Herein, we report a novel layered zinc silicate (LZS) photocatalyst synthesized by a liquid-phase epitaxial growth route using silica derived from vermiculite, a layered silicate clay mineral, as both the lattice-matched substrate and Si source. The epitaxial growth of LZS is limited in the 2D directions, thus generating the vermiculite-type crystal structure and ultrathin nanosheet morphology with thicknesses of 8–15 nm and a lateral size of about 200 nm. Experimental observations and DFT calculations indicated that LZS has a superior band alignment for the degradation of organic pollutants and reduction of CO2 to CO. The material exhibited efficient photocatalytic performance for 4-chlorophenol (4-CP) degradation and CO2 conversion into CO and is the first example of a claylike 2D photocatalyst with strong photooxidation and photoreduction capabilities.

A combined experimental and computational investigation on the unusual molecular mechanism of the lossen rearrangement reaction activated by carcinogenic halogenated quinones

The classic Lossen rearrangement is a wellknown reaction describing the transformation of an Oactivated hydroxamic acid into the corresponding isocyanate. In this study, we found that chlorinated benzoquinones (CnBQ) serve as a new class of agents for the activation of benzohydroxamic acid (BHA), leading to Lossen rearrangement. Compared to the classic one, this new kind of CnBQ-activated Lossen rearrangement has the following unique characteristics: (1) The stability of CnBQ-activated BHA intermediates was found to depend not only on the degree but also on the position of Cl-substitution on CnBQs, which can be divided into two subgroups. (2) It is the relative energy of the anionic CnBQ-BHA intermediates that determine the rate of this CnBQ-activated rearrangement, which is the rate-limiting step, and the Cl or H ortho to the reaction site at CnBQ is crucial for the stability of the anionic intermediates. (3) A pKa-activation energy correlation was observed, which can explain why the correlation exists between the rate of the rearrangement and the acidity of the conjugate acid of the anionic leaving group, the hydroxlated quinones. These findings may have broad implications for future research on halogenated quinoid carcinogens and hydroxamate biomedical agents.