824-69-1

Basic information

• Product Name: 2,5-DICHLOROHYDROQUINONE
• Synonyms: 2,5-DICHLOROHYDROQUINONE;2,5-Dichloro-1,4-benzenediol;2,5-Dichloro-1,4-dihydroxybenzene;2,5-Dichloro-1,4-hydroquinone;2,5-dichloro-4-benzenediol;2,5-Dichloro-p-benzohydroquinone;2,5-Dichloro-p-hydroquinone;Hydroquinone, 2,5-dichloro-
• CAS NO: 824-69-1
• Molecular Formula: C₆H₄Cl₂O₂
• Molecular Weight: 179
• EINECS: 212-533-8
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 824-69-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: 168-171 °C(lit.)
• Boiling Point: 255.02°C (rough estimate)
• Flash Point: 119.5 °C
• Appearance: almost white to pink-brown crystalline powder
• Density: 1.4512 (rough estimate)
• Vapor Pressure: 0.00332mmHg at 25°C
• Refractive Index: 1.4420 (estimate)
• PKA: 7.96±0.23(Predicted)
• CAS DataBase Reference: 2,5-DICHLOROHYDROQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DICHLOROHYDROQUINONE(824-69-1)
• EPA Substance Registry System: 2,5-DICHLOROHYDROQUINONE(824-69-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 824-69-1(Hazardous Substances Data)

Usage

Description

2,5-Dichlorohydroquinone (2,5-DCHQ) is a hydroquinone derivative characterized by the presence of chloro groups at the 2 and 5 positions. It is an almost white to pink-brown crystalline powder that can be synthesized by reducing 2,5-dichloroquinone using sodium dithionite (Na2S2O4). 2,5-DICHLOROHYDROQUINONE has been studied for its chemical reactions and transformations, such as its conversion to 2-chloromaleylacetate using PcpA protein isolated from Escherichia coli. Additionally, 2,5-DCHQ is reported to be a degradation product of 2,4,5-trichlorophenoxyacetic acid and γ-hexachlorocyclohexane.

Uses

Used in Chemical Synthesis:
2,5-Dichlorohydroquinone is used as a chemical intermediate in the synthesis of various organic compounds. Its unique structure with chloro substitutions at specific positions allows for targeted functionalization and the formation of diverse chemical products.
Used in Environmental Research:
As a degradation product of certain chlorinated compounds, 2,5-DCHQ plays a role in environmental research, particularly in understanding the fate and transformation of pollutants in the environment. This knowledge can contribute to the development of strategies for pollution control and remediation.
Used in Material Science:
The properties of 2,5-Dichlorohydroquinone, such as its crystalline nature and chemical reactivity, may find applications in material science. For instance, it could be utilized in the development of new materials with specific characteristics, such as improved stability or reactivity, for various industrial applications.
Please note that the specific applications of 2,5-Dichlorohydroquinone in different industries are not provided in the materials. The uses listed above are inferred based on the general properties and characteristics of the compound. Further research and information would be required to confirm these applications and identify additional uses in various industries.

InChI:InChI=1/C6H4Cl2O2/c7-3-1-5(9)4(8)2-6(3)10/h1-2,9-10H

Upstream product

• 64-17-5 ethanol 
• 57165-98-7 2,5,6-trichloro-cyclohex-2-ene-1,4-dione 
• 123-31-9 hydroquinone 
• 1221-72-3 Bis(p-methoxyphenyl)diazomethan 
• 1143-91-5 bis(4-methylphenyl)diazomethane 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 
• 150-76-5 4-methoxy-phenol 
• 908093-98-1 diazodiphenylmethane 
• 92-85-3 Thianthrene 
• 67-66-3 chloroform 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 

Downstream Products

• 71155-99-2 2,5-dichlorohydroquinone diacetate 
• 114446-88-7 1,4-bis-(10-bromo-decyloxy)-2,5-dichloro-benzene 
• 2675-77-6 1,4-dichloro-2,5-dimethoxybenzene 
• 105640-75-3 1,4-dichloro-2,5-bis-(2,3-epoxy-propoxy)-benzene 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 
• 3225-29-4 p-benzosemiquinone radical anion 
• 74-31-7 N,N'-diphenyl-1,4-phenylenediamine 
• 122-37-2 4-anilinophenol 
• 130442-28-3 4-tetradecyloxy-2,5-dichlorophenol 
• 134044-81-8 2,5-dichloro-4-hydroxyphenoxyl radical 
• 34865-89-9 p-hydroxydiphenylamine radical 
• 89284-69-5 2-chloro-5-hydroxy-1,4-benzoquinone 
• 6172-33-4 1,4-diallyloxy-2,5-dichlorobenzene 
• 144092-24-0 (tetrachloro-p-phenylenedioxy)-di-acetic acid 

Relevant articles and documents

Mechanisms of hydride abstractions by quinones

The kinetics of the hydride abstractions by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) from 13 C-H hydride donors (acyclic 1,4-dienes, cyclohexa-1,4-dienes, dihydropyridines), tributylstannane, triphenylstannane, and five borane complexes (amine-boranes, carbene-boranes) have been studied photometrically in dichloromethane solution at 20 °C. Analysis of the resulting second-order rate constants by the correlation log k2(20°C) = sN(E + N) (J. Am. Chem. Soc. 2001, 123, 9500) showed that the hydride abstractions from the C-H donors on one side and the Sn-H and B-H hydride donors on the other follow separate correlations, indicating different mechanisms for the two reaction series. The interpretation that the C-H donors transfer hydrogen to the carbonyl oxygen of DDQ while Sn-H and B-H hydride donors transfer hydride to a cyano-substituted carbon of DDQ is supported by quantum-chemical intrinsic reaction coordinate calculations and isotope labeling experiments of the reactions of D8-cyclohexa-1,4-diene, Bu3SnD, and pyridine·BD3 with 2,5-dichloro-p-benzoquinone. The second-order rate constants of the reactions of tributylstannane with different quinones correlate linearly with the electrophilicity parameters E of the quinones, which have previously been derived from the reactions of quinones with -nucleophiles. The fact that the reactions of Bu3SnH with quinones and benzhydrylium ions are on the same log k2 vs E (electrophilicity) correlation shows that both reaction series proceed by the same mechanism and illustrates the general significance of the reactivity parameters E, N, and sN for predicting rates of polar organic reactions.

Reactivity of iPrPCPIrH4 with para-benzoquinones

In the interest of investigating new hydrogen acceptors for pincer–iridium catalyzed dehydrogenations with the ability to be catalytically recycled, a series of para-benzoquinones have been reacted with iPrPCPIrH4 in various solvents and conditions. Preliminary results indicate that a wide range of quinones are capable of dehydrogenating iPrPCPIrH4, and that several turn-overs in alcohol dehydrogenation by iPrPCPIr are possible at room temperature using benzoquinone acceptors. However, strong acceptor–catalyst interactions are inhibitory toward catalysis when the acceptor is used in excess. A new class of (bis)-η2 pi-adducts, formed between iPrPCPIr and benzoquinones, nicknamed “barber-chairs”, has been identified and 3 examples have been characterized.

Diels-Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid

This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids. The products were accomplished by the Diels-Alder cycloaddition reaction and their mechanistic pathways have been formulated. The impact of C2 and C2,5 substituents of the p-quinones on the cycloaddition reaction has been explored. Remarkably, it is the first report to explore this kind of in situ generated diene for the Diels-Alder cycloaddition reaction.