695-99-8

Basic information

• Product Name: 2-CHLORO-1,4-BENZOQUINONE
• Synonyms: benzoquinone,2-chloro-;Chloro-1,4-benzoquinone;Chloro-p-benzoquinone;Chloroquinone;Monochloro-p-benzoquinone;Monochloroquinone;p-Benzoquinone, 2-chloro-;2-CHLORO-1,4-BENZOQUINONE
• CAS NO: 695-99-8
• Molecular Formula: C₆H₃ClO₂
• Molecular Weight: 142.54
• Product Categories: C3 to C6;Carbonyl Compounds;Ketones
• Mol File: 695-99-8.mol

Chemical Properties

• Melting Point: 52-57 °C
• Boiling Point: 210℃
• Flash Point: 83℃
• Appearance: Yellow to brown/Crystals
• Density: 1.40
• Vapor Pressure: 0.196mmHg at 25°C
• Refractive Index: 1.4620 (estimate)
• CAS DataBase Reference: 2-CHLORO-1,4-BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-1,4-BENZOQUINONE(695-99-8)
• EPA Substance Registry System: 2-CHLORO-1,4-BENZOQUINONE(695-99-8)

Safety Data

• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-15-10
• Safety Statements: 26-37/39-43-36-7/8
• WGK Germany: 3
• Hazardous Substances Data: 695-99-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-1,4-benzoquinone is used as a synthetic intermediate for the preparation of various organic compounds, particularly chloro derivatives. Its reactivity allows it to participate in a range of chemical reactions, making it a valuable component in the synthesis of complex molecules.
Used in the Preparation of Prenylnaphthohydroquinone Derivatives:
Specifically, 2-chloro-1,4-benzoquinone may be utilized in the preparation of chloro derivatives of prenylnaphthohydroquinone. This application takes advantage of its chemical properties to produce novel compounds with potential applications in various industries, such as pharmaceuticals or materials science.

InChI:InChI=1/C6H3ClO2/c7-5-3-4(8)1-2-6(5)9/h1-3H

Upstream product

• 106-51-4 p-benzoquinone 
• 108-43-0 3-monochlorophenol 
• 615-67-8 chloro-p-hydroquinone 
• 95-77-2 3,4-dichlorophenol 
• 120-83-2 2,4-dichlorophenol 
• 615-66-7 2-chloro-p-phenylenediamine 
• 100-66-3 methoxybenzene 
• 152506-88-2 (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)palladium(II) acetate 
• 50890-67-0 4,5-Diazafluoren-9-one 
• 3375-31-3 palladium diacetate 
• 89-64-5 p-chloro-o-nitrophenol 
• 56133-30-3 1,4-dihydro-1-(4-methoxybenzyl)pyridine-3-carboxamide 
• 19350-55-1 1-(4-chlorobenzyl)-1,4-dihydronicotinamide 
• 69565-22-6 1-(2,4-dichlorobenzyl)-1,4-dihydronicotinamide 

Downstream Products

• 4733-50-0 2,3-dicyano-1,4-hydroquinone 
• 3962-98-9 chloro-[1,4]benzoquinone; compound with hexamethylbenzene 
• 116571-85-8 chloro-[1,4]benzoquinone-4-semicarbazone 
• 3421-08-7 2,5-bis(phenylamino)-1,4-benzoquinone 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 
• 608-44-6 2,3-dichlorohydroquinone 
• 824-69-1 2,5-dichloro-1,4-hydroquinone 
• 20103-10-0 2,6-dichloro-1,4-benzenediol 
• 13362-35-1 2-chloro-1,4-benzoquinone-4-oxime 
• 57981-99-4 2-chlorohydroquinone diacetate 
• 46008-81-5 tribromo-chloro-[1,4]benzoquinone 
• 30100-39-1 2-bromo-5-chlorohydroquinone 
• 615-67-8 chloro-p-hydroquinone 
• 859033-31-1 1,2,4-triacetoxy-5-chloro-benzene 

Relevant articles and documents

Glutathione Conjugation and Protein Adduction by Environmental Pollutant 2,4-Dichlorophenol in Vitro and in Vivo

2,4-Dichlorophenol (2,4-DCP), an environmental pollutant, was reported to cause hepatotoxicity. The biochemical mechanisms of 2,4-DCP induced liver injury remain unknown. The present study showed that 2,4-DCP is chemically reactive and spontaneously react

Photochemical transformations of 2, 6-dichlorophenol and 2-chlorophenol with superoxide ions in the atmospheric aqueous phase

The possible photochemical transformation pathways of chlorophenols (2, 6-dichlorophenol and 2-chlorophenol) with superoxide anion radical (O2·?) were studied by steady-state irradiation and 355 nm laser flash photolysis technique. O

Surface decorated coral-like magnetic BiFeO3 with Au nanoparticles for effective sunlight photodegradation of 2,4-D and E. coli inactivation

In this report, gold nanoparticle-decorated on the coral-like magnetic BiFeO3 (Au-BiFeO3) composite has been successfully fabricated by facile two-steps hydrothermal technique. Incorporation of Au nanoparticles on the BiFeO3/su

Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels–Alder Reactions

An efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene-1,4-diols by a chiral phosphoric acid catalyzed quinone Diels–Alder reaction with dienecarbamates is reported. The nature of the protecting group on the diene is key to the success of achieving high enantioselectivity. The divergent “redox” selectivity is controlled by using an adequate amount of quinones. Reversible redox switching without erosion of enantioselectivity was possible from individual redox isomers.

Can Donor Ligands Make Pd(OAc)2a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria

Palladium(II)-catalyzed oxidation reactions represent an important class of methods for selective modification and functionalization of organic molecules. This field has benefitted greatly from the discovery of ancillary ligands that expand the scope, reactivity, and selectivity in these reactions; however, ancillary ligands also commonly poison these reactions. The different influences of ligands in these reactions remain poorly understood. For example, over the 60-year history of this field, the PdII/0 redox potentials for catalytically relevant Pd complexes have never been determined. Here, we report the unexpected discovery of (L)PdII(OAc)2-mediated oxidation of hydroquinones, the microscopic reverse of quinone-mediated oxidation of Pd0 commonly employed in PdII-catalyzed oxidation reactions. Analysis of redox equilibria arising from the reaction of (L)Pd(OAc)2 and hydroquinones (L = bathocuproine, 4,5-diazafluoren-9-one), generating reduced (L)Pd species and benzoquinones, provides the basis for determination of (L)PdII(OAc)2 reduction potentials. Experimental results are complemented by density functional theory calculations to show how a series of nitrogen-based ligands modulate the (L)PdII(OAc)2 reduction potential, thereby tuning the ability of PdII to serve as an effective oxidant of organic molecules in catalytic reactions.

Degradation of substituted phenols with different oxygen sources catalyzed by Co(II) and Cu(II) phthalocyanine complexes

Research on substituted phenol degradations has received substantial attention. In this work, effective Co(II) and Cu(II) phthalocyanine complexes as catalysts were studied to degrade toxic phenols to harmless products. The effect of various process parameters, such as initial concentration of phenol, catalyst, oxygen sources, and temperature on the degradation reaction was investigated to achieve maximum degradation efficiency. The catalytic activities of Co(II) and Cu(II) phthalocyanines were evaluated for oxidation of phenolic compounds such as p-nitrophenol, o-chlorophenol, 2,3-dichlorophenol, and m-methoxyphenol. Co(II) phthalocyanine displayed good catalytic performance in degradation of 2,3-dichlorophenol to 2,3-dichlorobenzaldehyde and 2,3-dichloro-1,4-benzoquinone with the highest TON and TOF values within 3 h at 50 °C. The fate of catalyst during the degradation process was followed by UV–Vis spectroscopy.

(E)-4-(4-(3-(2-fluoro-5-(trifluoromethyl)phenyl)acryloyl)phenoxy)Substituted Co(II)and Cu(II)phthalocyanines and their catalytic activities on the oxidation of phenols

Phenols from various man-made activities pose threats to public health and aquatic ecosystems. A number of technologies (e.g., adsorption, oxidation, and biological methods)have been proposed and tested to remove phenolic compounds from different sources. Among these technologies, oxidation process is considered one of the most efficient tools for abating phenolic compounds because of low cost, easy scalability, and ecofriendly production. In this work, we aim to synthesize and characterize potential catalysts (Co(II)and Cu(II)phthalocyanines 6 and 7)for phenolic compounds oxidation. Different parameters influenced the oxidation process were determined and phenolic compounds oxidize to the less harmful products with high conversion and yield in the presence of Co(II)and Cu(II)phthalocyanine catalysts.

Activated Carbon-Promoted Dehydrogenation of Hydroquinones to Benzoquinones, Naphthoquinones, and Anthraquinones under Molecular Oxygen Atmosphere

We found that the activated carbon-molecular oxygen system promotes the conversion of hydroquinones to benzoquinones, naphthoquinones, and anthraquinones, which are often found in natural products and pharmaceuticals. In particular, the one-pot synthesis of naphthoquinones and anthraquinones involving a Diels-Alder reaction is a useful protocol for this purpose.

The impact of an isoreticular expansion strategy on the performance of iodine catalysts supported in multivariate zirconium and aluminum metal-organic frameworks

Iodine functionalized variants of DUT-5 (Al) and UiO-67 (Zr) were prepared as expanded-pore analogues of MIL-53 (Al) and UiO-67 (Zr). They were prepared using a combination of multivariate and isorecticular expansion strategies. Multivariate MOFs with a 25% iodine-containing linker was chosen to achieve an ideal balance between a high density of catalytic sites and sufficient space for efficient diffusion. Changes to the oxidation potential of the catalyst as a result of the pore-expansion strategy led to a decrease in activity with electron rich substrates. On the other hand, these larger frameworks proved to be more efficient catalysts for substrates with higher oxidation potentials. Recyclability tests for these larger MOFs showed sustained catalytic activity over multiple recycles.

New peripherally tetra-[trans-3,7-dimethyl-2,6-octadien-1-ol] substituted metallophthalocyanines: synthesis, characterization and catalytic activity studies on the oxidation of phenolic compounds

In this paper, we elucidated the synthesis, characterization, and investigation of catalytic activity studies of new metallophthalocyanines 4 and 5 as the catalyst for phenolic compounds oxidation by trying different types of oxygen sources. The structural characterization of the products was made by a combination of elemental analysis, FT-IR, LC-MS/MS (for phthalonitrile derivative?3), MALDI-TOF mass spectral data (for metallophthalocyanines 4–7), UV–vis spectroscopy (for metallophthalocyanines 4–7), 1H NMR and 13C NMR spectroscopies (for compounds 3 and 6). The synthetic routes for the (trans-3,7-dimethyl-2,6-octadien-1-ol) substituted phthalonitrile derivative 3 and corresponding metallophthalocyanines 4–7 are outlined in Scheme 1. The MPc complexes 4–7 were synthesized via cyclotetramerization of compound 3 in the presence of the corresponding anhydrous metal salts (CoCl2 for 4, CuCl2 for 5, Zn(CH3COO)2 for 6 and MnCl2 for 7) in dry n-pentanol as solvent and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as strong base at reflux temperature under nitrogen gas. Phthalocyanines and their metal complexes, in general, display poor solubility in most of the organic solvents, however, the synthesized metallophthalocyanine complexes 4–7 were highly soluble in common organic solvents because of the introduction of the methyl groups on alkyl chains of peripheral arms. The catalytic activity of compounds 4 and 5 was evaluated for the oxidation of phenolic compounds such as 4-nitrophenol, o-chlorophenol, 2,3-dichlorophenol, and p-methoxyphenol. CoPc 4 displayed good catalytic performance with a full oxidation of 4-nitrophenol into the corresponding benzoquinone and hydroquinone with the highest TON and TOF values within 3?h.