Tetrachlorohydroquinone

Base Information

• Chemical Name: Tetrachlorohydroquinone
• CAS No.: 87-87-6
• Deprecated CAS: 29764-02-1
• Molecular Formula: C6H2 Cl4 O2
• Molecular Weight: 247.893
• Hs Code.: 2908199090
• European Community (EC) Number: 201-779-1
• NSC Number: 100888,4858
• UNII: 5P245C48WP
• DSSTox Substance ID: DTXSID8058958
• Nikkaji Number: J54.019F
• Wikidata: Q27102186
• Metabolomics Workbench ID: 50747
• ChEMBL ID: CHEMBL2074639
• Mol file: 87-87-6.mol

Synonyms:1,4-TCHQ;2,3,5,6-tetrachlorohydroquinone;tetrachloro-1,4-hydroquinone

Chemical Property of Tetrachlorohydroquinone

Chemical Property:

• Appearance/Colour: tan-coloured or yellowish powder
• Vapor Pressure: 0.00156mmHg at 25°C
• Melting Point: 238-240ºC
• Refractive Index: 1.4813 (estimate)
• Boiling Point: 286.2 ºC
• PKA: 5.54±0.33(Predicted)
• Flash Point: 126.9ºC
• PSA: 40.46000
• Density: 1.848 g/cm³
• LogP: 3.71140
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Sparingly), Methanol (Slightly, Heated)
• Water Solubility.: 21.5mg/L(temperature not stated)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 247.877940
• Heavy Atom Count: 12
• Complexity: 134

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tetrachlorohydroquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1(=C(C(=C(C(=C1Cl)Cl)O)Cl)Cl)O
• Description: Tetrachlorohydroquinone (TCHQ) is a metabolite of the organochlorine biocide pentachlorophenol. It is cytotoxic to RTL-W1 rainbow trout liver cells (EC50 = 1.55 μM in a neutral red assay). TCHQ increases production of reactive oxygen species (ROS), inhibits apoptosis, and induces loss of the mitochondrial membrane potential and necrosis in splenocytes. In vivo, TCHQ induces glutathione (GSH) depletion in mouse liver.
• Uses: Tetrachlorohydroquinone is a chlorinated hydroquinone compound used as an analytical standard.

Technology Process of Tetrachlorohydroquinone

There total 125 articles about Tetrachlorohydroquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

chloranil (118-75-2) → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone (4359-97-1)

Guidance literature:

With 4,4'-Methylenebis(2,6-di-tert-butylphenol); In toluene; at 110 ℃; for 2h;

Reference yield: 91.0%

3,4-dihydro-2H-pyran (110-87-2) + chloranil (118-75-2) → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6)

Guidance literature:

With oxygen; toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 83 ℃; for 0.5h; under 760.051 Torr; Reflux;

DOI:10.1039/C6OB02006B

Reference yield: 90.0%

C22H21N + chloranil (118-75-2) → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + 2,4-diphenyl-6-methylquinoline (73402-92-3)

Guidance literature:

In 1,2-dichloro-ethane; at 80 ℃;

DOI:10.1055/s-0039-1691740

upstream raw materials:

2,5-Dichloro-1,4-benzoquinone

phosphoric acid diethyl ester-(2,3,5,6-tetrachloro-4-hydroxy-phenyl ester)

2,6-dichloro-1,4-benzoquinone

2,3,6-trichloro-1,4-benzoquinone

Downstream raw materials:

2,3,5,6-tetrachloro-1,4-bis(benzyloxy)benzene

1,4-diethoxy-2,3,5,6-tetrachloro-benzene

1,4-Bis-acetylcarbamoyloxy-2,3,5,6-tetrachlor-benzol

Tetrachlorohydroquinone monobenzyl ether

Refernces

• 1、 Larionov, S.V.,Kosareva, L.A.,Boguslavskii, E.G.. "OXIDATION OF PALLADIUM(II) CHELATES WITH 1,2-HYDROXYLAMINOOXIMES". . p. 2374 - 2377. Retrieved 1984.
• 2、 Xue, Jie,Xu, Jian-Wei,Yang, Li,Xu, Jian-Hua. "Photoinduced reactions of chloranil with 1,1-diarylethenes and product photochemistry-intramolecular [2 + 2] (ortho-)cycloadditions of excited enedione's C=C double bond with substituted benzene ring". . p. 30 - 40. Retrieved 2000.
• 3、 Cheng, Dongping,Pu, Yueqi,Shen, Jing,Xu, Xiaoliang,Yan, Jizhong,Yan, Xianhang. "Synthesis of 2,4-Diarylquinoline Derivatives via Chloranil-Promoted Oxidative Annulation and One-Pot Reaction". supporting information. p. 1833 - 1840. Retrieved 2020/06/08.
• 4、 -. "HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES". Paragraph 0097. . Retrieved 2018/09/21.