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Sigma-Aldrich

2,5-Dichloro-1,4-benzoquinone

98%

Synonyme(s) :

2,5-Dichloro-2,5-cyclohexadiene-1,4-dione, 2,5-Dichloro-p-benzoquinone

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About This Item

Formule empirique (notation de Hill):
C6H2Cl2O2
Numéro CAS:
615-93-0
Poids moléculaire :
176.98
Numéro CE :
210-453-8
Numéro MDL:
MFCD00041736
Code UNSPSC :
12352100
ID de substance PubChem :
24867059
Nomenclature NACRES :
NA.22

Pureté

98%

Pf

160-163 °C (lit.)

Chaîne SMILES 

ClC1=CC(=O)C(Cl)=CC1=O

InChI

1S/C6H2Cl2O2/c7-3-1-5(9)4(8)2-6(3)10/h1-2H

Clé InChI

LNXVNZRYYHFMEY-UHFFFAOYSA-N

Description générale

2,5-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.

Application

2,5-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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

B Vijaya Pandiyan et al.
Physical chemistry chemical physics : PCCP, 16(37), 19928-19940 (2014-08-15)
The competition between non-covalent interactions (NCIs), such as C-H∙∙∙O, C-H∙∙∙Cl, C-Cl∙∙∙O, C-Cl∙∙∙Cl-C, C-O∙∙∙C, C-Cl∙∙∙C and C-O∙∙∙π, in the isomers of the 2,5-dichloro-1,4-benzoquinone (DCBQ) dimer were investigated by quantum chemical calculations to study the properties of the ground and excited states.
Halogen bonding in 2, 5-Dichloro-1, 4-benzoquinone: Insights from experimental and theoretical charge density analysis.
Hathwar VR, et al.
Crystal Growth & Design, 11(5), 1855-1862 (2011)
Chun-Hua Huang et al.
Chemical research in toxicology, 28(5), 831-837 (2015-03-20)
Halogenated quinones (XQ) are a class of carcinogenic intermediates and newly identified chlorination disinfection byproducts in drinking water. Organic hydroperoxides (ROOH) can be produced both by free radical reactions and enzymatic oxidation of polyunsaturated fatty acids. ROOH have been shown
Virág Kiss et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 16(4), 519-526 (2016-12-13)
Substituted 1,4-benzoquinone (QR) derivatives are photosensitive in aqueous solution and form hydroquinones (QR-H
Construction of a photochemical reactor combining a CCD spectrophotometer and a LED radiation source.
Gombar M, et al.
Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology, 11(10), 1592-1595 (2012)
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