Chloranilic acid

Base Information

• Chemical Name: Chloranilic acid
• CAS No.: 87-88-7
• Deprecated CAS: 260353-37-5
• Molecular Formula: C6H2Cl2O4
• Molecular Weight: 208.985
• Hs Code.: 29147000
• European Community (EC) Number: 201-780-7
• NSC Number: 6108
• UNII: YJ8L3BB7Y4
• DSSTox Substance ID: DTXSID3058959
• Nikkaji Number: J1.055.803D,J9.875B
• Wikipedia: Chloranilic_acid
• Wikidata: Q3277941
• Mol file: 87-88-7.mol

Synonyms:2,5-dichloro-3,6-dihydroxy-p-benzoquinone;chloranilic acid

Chemical Property of Chloranilic acid

Chemical Property:

• Appearance/Colour: orange or red crystals or powder
• Vapor Pressure: 0.000111mmHg at 25°C
• Melting Point: ≥300 °C(lit.)
• Refractive Index: 1.654
• Boiling Point: 300.3 °C at 760 mmHg
• PKA: pK1:1.09;pK2:2.42 (25°C)
• Flash Point: 135.4 °C
• PSA: 74.60000
• Density: 1.93 g/cm³
• LogP: 1.15500
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in hot water and methanol. Insoluble in organic solvents.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 207.9330139
• Heavy Atom Count: 12
• Complexity: 306

Purity/Quality:

99% ^*data from raw suppliers

Chloranilic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

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)O)Cl)O
• Uses: Chloranilic acid is the reactant involved in:Acting as a proton donor in reactions studying dimensionality controlSynthesis of dimethylbipyridyl complexesSynthesis of (nonylbenzimidazolylmethyl)benzene for preparation of neutral altitudinal rotor-shaped dirhenium metallacyclesCharge-transfer reactions with metoprolol tartrateSalt formation with organic basesSynthesis of osmium metalla-rectangles with anticancer activity Chloranilic acid is a strong dibasic organic acid which exhibits electron-acceptor properties on one hand and acidic properties leading to formation of hydrogen bonds on the other hand.Chloranilic acid is used in spectrophotometry. It reacts with metal ions to form stable complexes. It is also used as a reactant in the preparation of dimethylbipyridyl complexes and (nonylbenzimidazolylmethyl)benzene. Further, it is used in charge-transfer reactions with metoprolol tartrate. It is also employed in the synthesis of osmium metalla-rectangles with anticancer activity. In addition to this, it has potential antibacterial activities against methicillin-resistant Staphylococcus aureus. Reacts with metal cations to form stable salts. Used in spectrophotometry: Hart, organic. Chem. Bull. 33, no. 3 (1961).

Technology Process of Chloranilic acid

There total 33 articles about Chloranilic acid 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:

chlorosulfonic acid (7790-94-5) + hydroquinone (123-31-9,8027-02-9) → Pentachlorophenol (87-86-5,67471-28-7) + 3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone (87-88-7) + chloranil (118-75-2)

Guidance literature:

at 150 - 160 ℃;

DOI:10.1007/BF01525572

Reference yield:

chloranil (118-75-2) → 3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone (87-88-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; Product distribution; Mechanism; Rate constant; various concentrattions of alkaline solutions;

DOI:10.1002/(SICI)1097-4601(1997)29:5<385::AID-KIN9>3.0.CO;2-Q

Reference yield:

dipotassium dichloro(chloranilato)palladate(II) (115185-75-6) → tetrachloropalladium anion (14349-67-8) + 3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone (87-88-7)

Guidance literature:

With hydrogenchloride; In hydrogenchloride; decomn. of K2(Pd(C-CA)Cl2) in aq. HCl;

upstream raw materials:

o-tetrachloroquinone

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

2-Hydroxy-3,5,6-tribrom-1,4-benzochinon

chloranil

Downstream raw materials:

pentachloroacetone

hudrochloranilic acid

3,7-Bis-(4-nitro-phenyl)-1H,5H-4,8-dioxa-1,2,5,6-tetraaza-anthraquinone

3,7-Bis-(3-nitro-phenyl)-1H,5H-4,8-dioxa-1,2,5,6-tetraaza-anthraquinone

Refernces

• 1、 Lafis,Konidari,Veltsistas,Tzerpos,Karayannis. "Kinetic study of the fast step of the alkaline hydrolysis of p-chloranil using stopped flow technique". . p. 385 - 391. Retrieved 1997.
• 2、 Refat, Moamen S.,Killa, Hamada M.A.,El-Sayed. "IR, 1H-NMR, UV-Vis and thermal studies on the rhodamine 6G chargetransfer complexes". experimental part. p. 137 - 146. Retrieved 2012/05/31.