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87-87-6 Usage


Tetrachlorohydroquinone (TCHQ) is a chlorinated hydroquinone compound and a metabolite of the organochlorine biocide pentachlorophenol. It is characterized by its light beige crystalline powder appearance and exhibits cytotoxic properties, particularly to RTL-W1 rainbow trout liver cells. TCHQ is known to increase reactive oxygen species (ROS) production, inhibit apoptosis, and induce loss of mitochondrial membrane potential and necrosis in splenocytes. Additionally, it causes glutathione (GSH) depletion in mouse liver.


Used in Analytical Chemistry:
Tetrachlorohydroquinone is utilized as an analytical standard in various chemical and environmental analyses. Its properties and reactivity make it a valuable reference compound for the development and calibration of analytical methods and instruments.
Used in Environmental Research:
TCHQ's cytotoxic and reactive characteristics are relevant in environmental research, particularly in studies focused on the effects of organochlorine compounds on aquatic life and ecosystems. Understanding its impact can help in the development of strategies to mitigate the harmful effects of such pollutants.
Used in Pharmaceutical Research:
Due to its cytotoxic properties, Tetrachlorohydroquinone may be studied in pharmaceutical research for its potential applications in drug development. Its effects on cellular processes like apoptosis and ROS production could provide insights into the mechanisms of action for new therapeutic agents.
Used in Material Science:
The chemical properties of TCHQ, such as its light beige crystalline powder form, may be of interest in material science for the development of new materials with specific properties or for use in various industrial applications.

Purification Methods

Crystallise the quinone from EtOH or AcOH/EtOH. Sublime it at 77o/0.6x10-3mm. The dibenzoyl derivative has m 233o. [Conant & Fieser J Am Chem Soc 45 2207 1923, Rabideau et al. J Am Chem Soc 108 8130 1986, Beilstein 6 H 851, 6 I 417, 6 II 846, 6 III 4436, 6 IV 5775.]

Check Digit Verification of cas no

The CAS Registry Mumber 87-87-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 87-87:
76 % 10 = 6
So 87-87-6 is a valid CAS Registry Number.



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017


1.1 GHS Product identifier

Product name tetrachlorohydroquinone

1.2 Other means of identification

Product number -
Other names Tetrachlorohydroquinone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:87-87-6 SDS

87-87-6Relevant articles and documents


, p. 1229 (1966)

Synthetic Photochemistry. XXX. The Addition Reactions of Cycloheptatriene with Some Aromatic p-Quinones

Mori, Akira,Takeshita, Hitoshi

, p. 1581 - 1584 (1985)

The photochemical reactions of cycloheptatriene with p-benzoquinone and 1,4-naphthoquinone yielded the spirocyclic ethers, which had 7-oxabicyclonona-2,4-diene structures, by the characteristic (6+2)? cycloaddition process.The latter quinone further produced the carboxylic (2+2)? and (6+2)? cycloadducts.

Pentachlorophenol hydroxylase, a poorly functioning enzyme required for degradation of pentachlorophenol by sphingobium chlorophenolicum

Hlouchova, Klara,Rudolph, Johannes,Pietari, Jaana M. H.,Behlen, Linda S.,Copley, Shelley D.

, p. 3848 - 3860 (2012)

Several strains of Sphingobium chlorophenolicum have been isolated from soil that was heavily contaminated with pentachlorophenol (PCP), a toxic pesticide introduced in the 1930s. S. chlorophenolicum appears to have assembled a poorly functioning pathway for degradation of PCP by patching enzymes recruited via two independent horizontal gene transfer events into an existing metabolic pathway. Flux through the pathway is limited by PCP hydroxylase. PCP hydroxylase is a dimeric protein that belongs to the family of flavin-dependent phenol hydroxylases. In the presence of NADPH, PCP hydroxylase converts PCP to tetrachlorobenzoquinone (TCBQ). The kcat for PCP (0.024 s -1) is very low, suggesting that the enzyme is not well evolved for turnover of this substrate. Structure-activity studies reveal that substrate binding and activity are enhanced by a low pKa for the phenolic proton, increased hydrophobicity, and the presence of a substituent ortho to the hydroxyl group of the phenol. PCP hydroxylase exhibits substantial uncoupling; the C4a-hydroxyflavin intermediate, instead of hydroxylating the substrate, can decompose to produce H2O2 in a futile cycle that consumes NADPH. The extent of uncoupling varies from 0 to 100% with different substrates. The extent of uncoupling is increased by the presence of bulky substituents at position 3, 4, or 5 and decreased by the presence of a chlorine in the ortho position. The effectiveness of PCP hydroxylase is additionally hindered by its promiscuous activity with tetrachlorohydroquinone (TCHQ), a downstream metabolite in the degradation pathway. The conversion of TCHQ to TCBQ reverses flux through the pathway. Substantial uncoupling also occurs during the reaction with TCHQ.

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones

Baschieri, Andrea,Amorati, Riccardo,Valgimigli, Luca,Sambri, Letizia

, p. 13655 - 13664 (2019/10/28)

Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.

Calix[4]pyrrole Hydridosilicate: The Elusive Planar Tetracoordinate Silicon Imparts Striking Stability to Its Anionic Silicon Hydride

Ebner, Fabian,Greb, Lutz

supporting information, p. 17409 - 17412 (2019/01/04)

Anionic hydridosilicates are highly reactive and strong hydride donors. In contrast, calix[4]pyrrole hydridosilicate is an entirely water-stable, anionic silicon hydride, which does not show hydridic reactivity. However, it still acts as an electron donor and enables the detection of a single electron transfer process in the reduction chemistry with hydridosilicates. Most important, these unusual properties are imparted by the unique planar structure of its elusive parent neutral silane-substantiating the effect of planar tetracoordinate silicon for the first time.

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