ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Aromatic hydrocarbons 2,5-Dichlorobenzo-1,4-quinone

2,5-Dichlorobenzo-1,4-quinone

2,5-Dichlorobenzo-1,4-quinone Basic information
Product Name:2,5-Dichlorobenzo-1,4-quinone
Synonyms:2,5-Cyclohexadiene-1,4-dione,2,5-dichloro-;2-(2,5-dichlorophenyl)cyclohexa-2,5-diene-1,4-dione;2,5-Dichloro-1,4-benzoquinone 98%;2,5-Dichlorchinon;2,5-Dichloro-2,5-cyclohexa-diene-1,4-dione;2,5-Dichlorobenzo-1,4-quinone;2,5-Dichlorobenzoquinone;2,5-dichloro-p-benzoquinon
CAS:615-93-0
MF:C6H2Cl2O2
MW:176.98
EINECS:210-453-8
Product Categories:Anthraquinones, Hydroquinones and Quinones;Benzoquinones;C3 to C6;Carbonyl Compounds;Ketones
Mol File:615-93-0.mol
2,5-Dichlorobenzo-1,4-quinone Structure
2,5-Dichlorobenzo-1,4-quinone Chemical Properties
Melting point 160-163 °C(lit.)
Boiling point 251.81°C (rough estimate)
density 1.5138 (rough estimate)
refractive index 1.4595 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility soluble in Methanol
form powder to crystal
color Light yellow to Yellow to Orange
Water Solubility Insoluble in water.
Stability:Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference615-93-0(CAS DataBase Reference)
NIST Chemistry Reference2,5-Cyclohexadiene-1,4-dione, 2,5-dichloro-(615-93-0)
EPA Substance Registry System2,5-Cyclohexadiene-1,4-dione, 2,5-dichloro- (615-93-0)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS DK3990000
TSCA Yes
HS Code 2914698090
MSDS Information
ProviderLanguage
2,5-Dichlorobenzo-1,4-quinone English
SigmaAldrich English
2,5-Dichlorobenzo-1,4-quinone Usage And Synthesis
Chemical Propertiesyellow powder
Uses2,5-Dichloro-1,4-benzoquinone may be used in the following processes:
  • As a starting material in the synthesis of asterriquinone D.
  • As a model to study the utility of a novel photoreactor with LED (light-emitting diode) light source and a fibre-optic CCD (charge-coupled device) spectrophotometer.
  • 2,5-dichloro-3,6-bi(3-indolyl)-1,4-hydroquinone synthesis by palladium catalyzed reaction with indole.
General Description2,5-Dichloro-1,4-benzoquinone (DCBQ) is a halogenated quinone. DCBQs are carcinogenic intermediates.They have benn identified as chlorination disinfection byproducts in drinking water. DCBQ has been reported to increse the decomposition of a model ROOH tert-butylhydroperoxide, via formation of t-butoxyl radicals. The isomers of the DCBQ dimer have been investigated for the non-covalent interactions (NCIs) by quantum chemical calculations. Halogen bond present in 2,5-dichloro-1,4-benzoquinone have been investigated by experimental as well as theoretical charge density analysis. Its reaction with pyrrolidine has been investigated.
Purification MethodsRecrystallise it twice from 95% EtOH to give yellow needles [Beck et al. J Am Chem Soc 108 4018 1986]. The dioxime has m 278o(dec). [Beilstein 7 H 632, 7 I 346, 7 II 580, 7 III 3376, 7 IV 2081.]
2,5-Dichlorobenzo-1,4-quinone Preparation Products And Raw materials
Raw materialsHydrochloric acid-->Diethyl ether-->Hydrogen peroxide-->Acetonitrile-->Sulfuryl chloride-->1,4-Dimethoxybenzene-->Ceric ammonium nitrate-->2,6-DICHLORO-1,4-BENZOQUINONE-->Phenol
Preparation Products2,5-DICHLOROHYDROQUINONE
2,3,5-TRICHLORO-1,4-BENZOQUINONE Dichlorodifluoromethane 3,5-Dichlorobenzoic acid 2,5-diamino-3,6-dichloro-p-benzoquinone BENZAMIDE, N,N'-[(2,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE-1,4-DIYL)BIS(IMINO-4,1-PHENYLENE)]BIS- 2,5-DICHLORO-3,6-DIMETHYL-P-BENZOQUINONE CHLORANILIC ACID THORIUM SALT 2',4'-Dichloroacetophenone 2,3-Dimethoxy-5-methyl-p-benzoquinone 2,5-Dichlorobenzo-1,4-quinone BARIUM CHLORANILATE CHLORANILIC ACID LANTHANUM SALT 2,5-BIS(N-DIETHYLAMINO)-3,6-DICHLORO-P-BENZOQUINONE Terephthalic acid Dichlorodimethylsilane 1,4-Benzoquinone Chloranilic acid 2,5-BIS(1-MORPHOLINO)-3,6-DICHLORO-P-BENZOQUINONE
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