Chloranil

Base Information

• Chemical Name: Chloranil
• CAS No.: 118-75-2
• Deprecated CAS: 142655-99-0,856302-53-9,856302-53-9
• Molecular Formula: C6Cl4O2
• Molecular Weight: 245.877
• Hs Code.: 29147090
• European Community (EC) Number: 204-274-4
• ICSC Number: 0780
• NSC Number: 8432
• UNII: 01W5X7N5XV
• DSSTox Substance ID: DTXSID2020266
• Nikkaji Number: J5.304J
• Wikipedia: Chloranil
• Wikidata: Q629632
• Pharos Ligand ID: Z5DRS12S6CCZ
• Metabolomics Workbench ID: 55466
• ChEMBL ID: CHEMBL192627
• Mol file: 118-75-2.mol

Synonyms:2,3,5,6-Tetrachloro-1,4-benzoquinone;Chloranil;Coversan;Reranil;Spergon;Tetrachloro 1,4 benzoquinone;Tetrachloro-1,4-benzoquinone;Vulklor

Chemical Property of Chloranil

Chemical Property:

• Appearance/Colour: Golden crystals
• Vapor Pressure: 1 hPa (71 °C)
• Melting Point: 295-296 ºC (dec.)
• Boiling Point: 269.5 ºC at 760 mmHg
• Flash Point: 111.7 ºC
• PSA: 34.14000
• Density: 1.8 g/cm³
• LogP: 2.51660
• Storage Temp.: Store below +30°C.
• Solubility.: 0.25g/l practically insoluble
• Water Solubility.: insoluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 245.862290
• Heavy Atom Count: 12
• Complexity: 278

Purity/Quality:

90%,98% ^*data from raw suppliers

Tetrachloro-1,4-benzoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N,Xn
• Hazard Codes: Xi,N,Xn
• Statements: 36/38-50/53-20
• Safety Statements: 37-60-61-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones, Halogenated
• Canonical SMILES: C1(=C(C(=O)C(=C(C1=O)Cl)Cl)Cl)Cl
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. Exposure at high levels could cause unconsciousness.
• Uses: antipsoriatic Tetrachloro-1,4-benzoquinone is a potential intermediate in the process of pentachlorophenol-induced carcinogenicity. Agricultural fungicide, dye intermediate, reagent. manufacture of electrodes for pH measurement. p-Chloranil is used as a dye intermediate, oxidizing agent, vulcanizing agent and dehydrogenation reagent. It is also used to make chloranil electrodes for pH measurements. Further, it serves as a hydrogen acceptor and used for the aromatization reactions such as conversion of cyclohexadienes to the benzene derivatives. It is used to test the secondary amine. In addition to this, it is employed as a precursor to prepare diaziquone, which is used as a cancer chemotherapeutic agent.

Technology Process of Chloranil

There total 376 articles about Chloranil 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: 8.5%

Pentachlorophenol (87-86-5,67471-28-7) → o-tetrachloroquinone (2435-53-2) + chloranil (118-75-2)

Guidance literature:

With ammonium nitrate; trifluoroacetic anhydride; In dichloromethane; at 25 - 30 ℃; for 4h;

DOI:10.1021/jo00328a013

Reference yield: 3.5%

3,5-dichlorosalicylic acid (320-72-9) → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + 3,5,6-Trichloro-2-hydroxybenzoic acid (40932-60-3) + chloranil (118-75-2) + tri(3,5,6-trichlorosalicylide)

Guidance literature:

With sulfuric acid; chlorine; at 80 - 90 ℃; for 15h;

Reference yield:

aniline yellow (60-09-3) → benzene diazonium chloride (100-34-5) + [1,4]benzoquinone; phenoquinone (4370-52-9,20389-02-0,114661-55-1) + chloranil (118-75-2)

Guidance literature:

at 5 ℃;

upstream raw materials:

tetrachloromethane

acetic acid-(2,3,5,6-tetrachloro-N-nitro-anilide)

4-nitro-phenol

Pentachlorophenol

Downstream raw materials:

2,5-dichloro-3,6-bis-(2-methyl-aziridin-1-yl)-[1,4]benzoquinone

trichloro-(2-pyrrolidino-vinyl)-[1,4]benzoquinone

trichloro-(ξ-2-piperidino-vinyl)-[1,4]benzoquinone

2,5-Dichlor-3,6-dipiperidin-p-benzochinon

Refernces

• 1、 Lan, Qing,Cao, Meiyuan,Ye, Zhijun,Zhu, Jishu,Chen, Manjia,Chen, Xuequan,Liu, Chengshuai. "Effect of oxalate and pH on photodegradation of pentachlorophenol in heterogeneous irradiated maghemite System". . p. 198 - 206. Retrieved 2016.
• 2、 Chakraborty, Prateeti,Majumder, Ishani,Kara, Hulya,Chattopadhyay, Shyamal Kumar,Zangrando, Ennio,Das, Debasis. "Azido bridge mediated catecholase activity, electrochemistry and magnetic behavior of a dinuclear copper(II) complex of a phenol based "end-off" compartmental ligand". . p. 139 - 145. Retrieved 2015.
• 3、 Chang. "-". . p. 2921. Retrieved 1962.
• 4、 Labra-Espina, Marietta,Male, Keith B.,Luong, John H. T.. "A flow injection (FI) biosensor system for pentachlorophenol (PCP) using a substance recycling scheme". . p. 3291 - 3295. Retrieved 2000.
• 5、 Fukuzumi, Shunichi,Hong, Young Hyun,Lee, Yong-Min,Nam, Wonwoo. "Photocatalytic Hydrogen Evolution from Plastoquinol Analogues as a Potential Functional Model of Photosystem I". . p. 14838 - 14846. Retrieved 2020.
• 6、 Hofmann,A. W.. "-". . . Retrieved 1845.
• 7、 Denis. "". . . Retrieved 1926.
• 8、 Kazunga, Chikoma,Aitken, Michael D.,Gold, Avram. "Primary product of the horseradish peroxidase-catalyzed oxidation of pentachlorophenol". . p. 1408 - 1412. Retrieved 1999.
• 9、 Ho, Te-Fu L.,Bolton, James R.. "Toxicity changes during the UV treatment of pentachlorophenol in dilute aqueous solution". . p. 489 - 497. Retrieved 1998.
• 10、 Kawai et al.. "". . p. 77,81. Retrieved 1972.