634-85-5

Basic information

• Product Name: 2,3,5-TRICHLORO-1,4-BENZOQUINONE
• Synonyms: 2,3,5-TRICHLORO-1,4-BENZOQUINONE;2,3,5-Trichloro-2,5-cyclohexadiene-1,4-dione;2,3,5-Trichloro-p-benzoquinone;2,5-Cyclohexadiene-1,4-dione, 2,3,5-trichloro-;2,5-cyclohexadiene-1,4-dione,2,3,5-trichloro-;benzoquinone,2,3,5-trichloro-;p-Benzoquinone, 2,3,5-trichloro-;Trichloro-p-benzoquinone
• CAS NO: 634-85-5
• Molecular Formula: C₆HCl₃O₂
• Molecular Weight: 211.43
• Mol File: 634-85-5.mol

Chemical Properties

• Boiling Point: 303.59°C (rough estimate)
• Flash Point: 105 °C
• Appearance: /
• Density: 1.7291 (rough estimate)
• Vapor Pressure: 0.0164mmHg at 25°C
• Refractive Index: 1.4501 (estimate)
• CAS DataBase Reference: 2,3,5-TRICHLORO-1,4-BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-TRICHLORO-1,4-BENZOQUINONE(634-85-5)
• EPA Substance Registry System: 2,3,5-TRICHLORO-1,4-BENZOQUINONE(634-85-5)

Safety Data

• Hazardous Substances Data: 634-85-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3,5-Trichloro-1,4-benzoquinone is used as a precursor in the synthesis of various chemical compounds, including dyes and pharmaceuticals, due to its strong oxidizing properties.
Used in Research Laboratories:
In research settings, 2,3,5-trichloro-1,4-benzoquinone is utilized for its unique chemical properties, enabling the exploration of new chemical reactions and the development of novel compounds.
Used in Industrial Settings:
2,3,5-Trichloro-1,4-benzoquinone is employed in industrial applications for the production of specific chemical products, leveraging its strong oxidizing capabilities.
However, due to its hazardous nature, which includes potential irritation to the skin, eyes, and respiratory system, as well as possible carcinogenic effects, proper precautions must be taken when handling 2,3,5-trichloro-1,4-benzoquinone.

InChI:InChI=1/C6HCl3O2/c7-2-1-3(10)4(8)5(9)6(2)11/h1H

Upstream product

• 933-78-8 2,3,5-trichlorophenol 
• 58-90-2 2,3,4,6-tetrachlorophenol 
• 78647-87-7 4-bromo-2,3,6-trichloroanisole 
• 7647-01-0 hydrogenchloride 
• 108-95-2 phenol 
• 7664-93-9 sulfuric acid 
• 420133-77-3 2,3,6-trichloro-4-methoxy-aniline 
• 51-78-5 p-aminophenol hydrochloride 
• 7782-50-5 chlorine 
• 64981-10-8 2,3,6-trichloro p-aminophenol 
• 78647-85-5 trichloro-4-ethoxyphthalic acid 
• 64-17-5 ethanol 
• 608-94-6 2,3,5-trichloro-1,4-hydroquinone 
• 7697-37-2 nitric acid 

Downstream Products

• 5030-67-1 2,5-dianilino-3,6-dichloro-1,4-benzoquinone 
• 33876-90-3 anilino-trichloro-[1,4]benzoquinone 
• 877-13-4 5-hydroxyl-2,3,6-trichloro-1,4-benzoquinone 
• 125635-87-2 2,3,5-trichlorohydroquinone diacetate 
• 118-75-2 chloranil 
• 106-34-3 quinhydrone 
• 608-94-6 2,3,5-trichloro-1,4-hydroquinone 
• 118-74-1 hexachlorobenzene 
• 87-87-6 2,3,5,6-tetrachlorobenzene-1,4-diol 
• 87963-48-2 4-Amino-2,3,5-trichloro-4-hydroxy-cyclohexa-2,5-dienone 
• 87963-51-7 1,4-Diamino-2,3,5-trichloro-cyclohexa-2,5-diene-1,4-diol 
• 2235-01-0 dimethoxydiphenylmethane 
• 53692-29-8 N,N'-(2,5-dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,4-diyl)-bis-glycine diethyl ester 
• 5533-10-8 2,3,5,6-tetrachlorohydroquinone diacetate 

Relevant articles and documents

Mesolytic scission of C-C bonds as a probe for photoinduced electron transfer reactions of Quinones

Photoinduced electron transfer reactions of chlorinated benzoquinones are investigated using bibenzylic donors that undergo rapid fragmentation upon oxidation. The fragmentation rates and the quantum yields are used to probe the dynamics of back-electron transfer (BET) in two types of radical ion pairs. The triplet ion pairs formed by interception of excited state quinones give products with high quantum yields. The singlet ion pairs formed by irradiation of the charge-transfer (CT) complexes between the quinones and the donors undergo reactions with significantly lower efficiency. The advantage of the first method (triplet quenching) over the CT-irradiation depends on the energetics of BET. It is large for reactions with relatively small ΔGet for BET and it decreases for reactions with more negative ΔGbet. The indirectly obtained rates of BET are in excellent agreement with literature data for similar, but unreactive systems, and the rates of C-C bond scission in radical cations generated in these systems are consistent with the thermodynamics of these processes.

Selective halogenation of 1,4-benzoquinones and 1,4-naphthoquinones with copper(II) halide adsorbed on alumina

1,4-Benzoquinone or 1,4-naphthoquinone and their derivatives have been halogenated selectively at quinonoid positions with copper(II) halide adsorbed on neutral alumina followed by refluxing in halobenzene to give mono-, di-, tri- and tetra-haloquinones.

CHLORINATION OF 2,4,6-TRICHLOROPHENOL IN ACIDIC AQUEOUS MEDIUM

The course of chlorination of 2,4,6-trichlorophenol (I) in water and approximately 20percent sulfuric and hydrochloric acids has been investigated.In all these media the reaction gives primarily 2,4,6,6-tetrachloro-2,4-cyclohexadienone (II) which is subsequently chlorinated under formation of polychlorinated alicyclic ketones or isomerized to give the more stable 2,4,4,6-tetrachloro-2,5-cyclohexadienone (III), the precursor of further arising chlorinated 1,4-benzoquinones.The ratio of the arising polychlorinated alicyclic ketones to chlorinated 1,4-benzoquinones is significantly influenced by concentration of hydrogen chloride in the reaction medium.On the basis of model experiments, the reaction mechanism of exhaustive chlorination of 2,4,6-trichlorophenol has been suggested.

Nucleophilic Substitution on Perchloroindane; Reactions and Structural Reassignments

Nucleophilic substitution on perchloroindane (1) with ethoxide ion gives nonachloro-5-ethoxyindane (6), heptachloro-1,1,5-triethoxyindane (7), and 3,5,6-trichloro-4-ethoxy-2-trichlorovinylbenzoic acid (8).The results show that in perchloroindane (1) aroma