3,3',5,5'-Tetramethyldiphenoquinone

Base Information

• Chemical Name: 3,3',5,5'-Tetramethyldiphenoquinone
• CAS No.: 4906-22-3
• Deprecated CAS: 141339-04-0,19358-55-5,41395-97-5,83467-99-6,142763-32-4,19358-55-5,41395-97-5,83467-99-6
• Molecular Formula: C16H16O2
• Molecular Weight: 240.302
• Hs Code.: 2914299000
• European Community (EC) Number: 225-535-9
• NSC Number: 93973
• UNII: AEG52T9Y6H
• DSSTox Substance ID: DTXSID6063644
• Nikkaji Number: J262.524E
• Wikidata: Q72507616
• Mol file: 4906-22-3.mol

Synonyms:4906-22-3;3,3',5,5'-Tetramethyldiphenoquinone;3,3',5,5'-Tetramethyl-4,4'-diphenoquinone;Tetramethyldiphenoquinone;3,3'5,5'-Tetramethyl-4,4'-diphenoquinone;Diphenoquinone, 3,3',5,5'-tetramethyl-;(Bi-2,5-cyclohexadien-1-ylidene)-4,4'-dione, 3,3',5,5'-tetramethyl-;2,5-Cyclohexadien-1-one, 4-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-2,6-dimethyl-;4-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-2,6-dimethylcyclohexa-2,5-dien-1-one;3,3',5,5'-Tetramethyldiphenylquinone;AEG52T9Y6H;Tetramethyl-4,4'-biphenylquinone;EINECS 225-535-9;NSC 93973;NSC-93973;3,3,5,5-TETRAMETHYL-4,4-DIPHENOQUINONE;[Bi-2,5-cyclohexadien-1-ylidene]-4,4'-dione, 3,3',5,5'-tetramethyl-;NSC93973;2,6,2',6'-tetramethyldiphenoquinone;UNII-AEG52T9Y6H;SCHEMBL2741115;DTXSID6063644;3,5,5-Tetramethyldiphenoquinone;3,5,5'-Tetramethyldiphenoquinone;3,5,5'-Tetramethyldiphenylquinone;3,3,5,5-Tetramethyldiphenoquinone;AMY39486;MFCD00019448;STK672154;AKOS015902159;Diphenoquinone,3',5,5'-tetramethyl-;3,5,5'-Tetramethyl-4,4'-diphenoquinone;FT-0635476;2,2',6,6'-TETRAMETHYLDIPHENOQUINONE;2,2',6,6'-TETRAMETHYLDIPHENYLQUINONE;[Bi-2,4'-dione, 3,3',5,5'-tetramethyl-;3,3',5,5'-TERTRAMETHYL-4,4'-DIPHENOQUINONE;3,3',5,5'-TETRAMETHYL-4,4'-BIPHENOQUINONE;2, 4-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-2,6-dimethyl-;3,3',5,5'-TETRAMETHYL-[1,1'-BI(CYCLOHEXYLIDENE)]-2,2',5,5'-TETRAENE-4,4'-DIONE;3,3',5,5'-tetramethyl-1,1'-bi(cyclohexa-2,5-dien-1-ylidene)-4,4'-dione;4-(3,5-dimethyl-4-oxo-2,5-cyclohexadienylidene)-2,6-dimethyl-2,5-cyclohexadienone

Chemical Property of 3,3',5,5'-Tetramethyldiphenoquinone

Chemical Property:

• Melting Point: 205-207 °C
• Boiling Point: 375.1 °C at 760 mmHg
• Flash Point: 140.7 °C
• PSA: 34.14000
• Density: 1.123 g/cm³
• LogP: 3.23360
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 240.115029749
• Heavy Atom Count: 18
• Complexity: 503

Purity/Quality:

98%min ^*data from raw suppliers

3,3',5,5'-TETRAMETHYLDIPHENOQUINONE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C2C=C(C(=O)C(=C2)C)C)C=C(C1=O)C

Technology Process of 3,3',5,5'-Tetramethyldiphenoquinone

There total 40 articles about 3,3',5,5'-Tetramethyldiphenoquinone 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: 100.0%

2.6-dimethylphenol (576-26-1,25134-01-4) → 3,3',5,5'-tetramethyldiphenoquinone (4906-22-3)

Guidance literature:

With phosphovanadomolybdic acid; oxygen; under 750.075 Torr;

DOI:10.1016/j.molcata.2011.12.033

Reference yield: 100.0%

3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl (2417-04-1,60133-38-2) → 3,3',5,5'-tetramethyldiphenoquinone (4906-22-3)

Guidance literature:

With C₂₄H₁₃Cu₂F₉N₄O₇; dihydrogen peroxide; oxygen; In isopropyl alcohol; at 90 ℃; under 760.051 Torr;

DOI:10.1039/c1dt11065a

Reference yield: 98.0%

2.6-dimethylphenol (576-26-1,25134-01-4) → 3,3',5,5'-tetramethyldiphenoquinone (4906-22-3) + poly(2,6-dimethyl-1,4-phenyleneoxide), Mn 13E3, Mw/Mn 1.8; monomer(s): 2,6-dimethylphenol

Guidance literature:

With sodium hydroxide; sodium dodecyl-sulfate; potassium hexacyanoferrate(III); In water; at 50 ℃; for 6h;

DOI:10.1002/anie.200352764

upstream raw materials:

2.6-dimethylphenol

chloroform

3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl

2,6-di-tert-butylphenol

Downstream raw materials:

3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl

5,3',5'-Trimethyl-3-morpholin-4-ylmethyl-biphenyl-4,4'-diol

3-Dibutylaminomethyl-5,3',5'-trimethyl-biphenyl-4,4'-diol

3-Diethylaminomethyl-5,3',5'-trimethyl-biphenyl-4,4'-diol

Refernces

• 1、 Finkbeiner et al.. "". . p. 549. Retrieved 1966.
• 2、 Zombeck, Alan,Drago, Russell S.,Corden, Barry B.,Gaul, John H.. "Activation of Molecular Oxygen. Mechanistic Studies of the Oxidation of Hindered Phenols with Cobalt-Dioxygen". . p. 7580 - 7585. Retrieved 1981.
• 3、 Murugavel, Ramaswamy,Pothiraja, Ramasamy,Gogoi, Nayanmoni,Clerac, Rodolphe,Lecren, Lollita,Butcher, Ray J.,Nethaji, Munirathinam. "Synthesis, magnetic behaviour, and X-ray structures of dinuclear copper complexes with multiple bridges. Efficient and selective catalysts for polymerization of 2,6-dimethylphenol". . p. 2405 - 2410. Retrieved 2007.
• 4、 Saunders,Stark. "Studies in peroxidase action-XVII. Some general observations". . p. 1867 - 1872. Retrieved 1967.
• 5、 Zhang, Erpeng,Hou, Hongwei,Han, Huayun,Fan, Yaoting. "Syntheses, crystal structures of a series of copper(II) complexes and their catalytic activities in the green oxidative coupling of 2,6-dimethylphenol". . p. 1927 - 1937. Retrieved 2008.
• 6、 Engelmann, Claudia,Illner, Sabine,Kragl, Udo. "Laccase initiated C-C couplings: Various techniques for reaction monitoring". . p. 1591 - 1599. Retrieved 2015.
• 7、 Ar, Deniz,Kilpatrick, Alexander F. R.,Cula, Beatrice,Herwig, Christian,Limberg, Christian. "Transformation of Formazanate at Nickel(II) Centers to Give a Singly Reduced Nickel Complex with Azoiminate Radical Ligands and Its Reactivity toward Dioxygen". supporting information. p. 13844 - 13853. Retrieved 2021/05/04.
• 8、 -. "Method for synthesizing high-purity 3,3',5,5'-tetramethyl-4,4'-biphenyl diquinone through Cu-BTC catalysis". Paragraph 0018-0043. . Retrieved 2018/04/01.