Duroquinone

Base Information

• Chemical Name: Duroquinone
• CAS No.: 527-17-3
• Molecular Formula: C10H12 O2
• Molecular Weight: 164.204
• Hs Code.: 2914690090
• European Community (EC) Number: 208-409-8
• NSC Number: 2068
• UNII: X0Q8791R69
• DSSTox Substance ID: DTXSID50200659
• Nikkaji Number: J11.876A
• Wikipedia: Duroquinone
• Wikidata: Q2423089
• Metabolomics Workbench ID: 52302
• ChEMBL ID: CHEMBL151604
• Mol file: 527-17-3.mol

Synonyms:2,3,5,6-tetramethylbenzoquinone;duroquinone

Chemical Property of Duroquinone

Chemical Property:

• Appearance/Colour: YELLOW POWDER
• Vapor Pressure: 0.0672mmHg at 25°C
• Melting Point: 110-112 ºC(lit.)
• Refractive Index: 1.5220 (estimate)
• Boiling Point: 230.1 ºC at 760 mmHg
• Flash Point: 83.6 ºC
• PSA: 34.14000
• Density: 1.039 g/cm³
• LogP: 1.81100
• Storage Temp.: under inert gas (Argon)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 268

Purity/Quality:

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

Tetramethyl-1,4-benzoquinone ^*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

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)C)C)C
• Uses: Tetramethyl-1,4-benzoquinone is an antioxidant.

Technology Process of Duroquinone

There total 98 articles about Duroquinone 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%

Durohydroquinone (527-18-4) → Duroquinone (527-17-3,70128-24-4)

Guidance literature:

With oxygen; Nitrogen dioxide; In dichloromethane; at -10 ℃; for 6h; Rate constant; Mechanism; further nitrogen oxides as catalysts, other temp., also with labeled hydroquinones;

DOI:10.1021/jo00088a039

Reference yield: 99.7%

2,3,6-trimethylphenol (2416-94-6) + acetic acid (64-19-7,77671-22-8) → 2,3,5-Trimethyl-1,4-benzoquinone (935-92-2) + Duroquinone (527-17-3,70128-24-4) + pentamethylphenol (2819-86-5) + 1-methoxy-2,3,6-trimethylbenzene (21573-36-4) + 2,3,5-trimethyl-1,4-hydroquinone diacetate (7479-28-9) + 2,3,6-trimethylphenyl acetate (62687-45-0)

Guidance literature:

With peracetic acid; at 50 ℃; for 0.25h; Product distribution; Kinetics; Thermodynamic data;

Reference yield: 96.0%

4-Benzenesulfinyl-2,3,5,6-tetramethyl-phenol (169216-70-0) + trifluoroacetic anhydride (407-25-0) → Duroquinone (527-17-3,70128-24-4) + O-Trifluoracetyl-tetramethyl-hydrochinon (25181-90-2) + diphenyldisulfane (882-33-7)

Guidance literature:

In dichloromethane; at 0 ℃; for 0.0833333h; Yield given. Yields of byproduct given;

DOI:10.1039/c39950001013

upstream raw materials:

methylene chloride

1,2,4-Trimethylbenzene

2,3-Pentanedione

diacetyl peroxide

Downstream raw materials:

Durohydroquinone

phosphoric acid-(4-ethoxy-2,3,5,6-tetramethyl-phenyl ester)-diethyl ester

tetramethyl-1,4-benzoquinone-tetramethyl-1,4-hydroquinone

4-(triethylsilyloxy)-2,3,5,6-tetramethylphenoxy

Refernces

• 1、 Wieland,Baeuerlein. "-". . p. 1381. Retrieved 1967.
• 2、 Levanon, Haim,Regev, Ayelet,Galili, Tamar,Hugerat, Muhamad,Chang, Chi K.,Fajer, Jack. "Photoelectron Transfer between a Magnesium-Free-Base Porphyrin Heterodimer and Duroquinone. Selective Excitation and Time-Resolved EPR Studies". . p. 13198 - 13205. Retrieved 1993.
• 3、 James,Weissberger. "-". . p. 98,99, 103. Retrieved 1938.
• 4、 Cheong, Choon Boon,Frost, James R.,Donohoe, Timothy J.. "Pentamethylphenyl (Ph*) and Related Derivatives as Useful Acyl Protecting Groups for Organic Synthesis: A Preliminary Study". . p. 1828 - 1832. Retrieved 2020/10/06.