3,5-Di-tert-butyl-o-benzoquinone

Base Information

• Chemical Name: 3,5-Di-tert-butyl-o-benzoquinone
• CAS No.: 3383-21-9
• Molecular Formula: C14H20O2
• Molecular Weight: 220.312
• Hs Code.: 29146990
• European Community (EC) Number: 222-189-0
• NSC Number: 149061
• DSSTox Substance ID: DTXSID70187478
• Nikkaji Number: J80.711G
• Wikidata: Q83059179
• Pharos Ligand ID: UZSWPYFPN7FV
• ChEMBL ID: CHEMBL365161
• Mol file: 3383-21-9.mol

Synonyms:3,5-di-t-butyl-o-benzoquinone;3,5-di-tert-butyl-1,2-benzoquinone;3,5-DTBBQ

Chemical Property of 3,5-Di-tert-butyl-o-benzoquinone

Chemical Property:

• Appearance/Colour: dark red crystals or powder
• Vapor Pressure: 0.000976mmHg at 25°C
• Melting Point: 112-114°C(lit.)
• Refractive Index: 1.504
• Boiling Point: 302.7 °C at 760 mmHg
• Flash Point: 120.6 °C
• PSA: 34.14000
• Density: 1.027 g/cm³
• LogP: 3.08320
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Methanol (Very Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 220.146329876
• Heavy Atom Count: 16
• Complexity: 395

Purity/Quality:

3,5-Di-tert-butyl-o-benzoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: CC(C)(C)C1=CC(=O)C(=O)C(=C1)C(C)(C)C
• General Description: 3,5-DI-TERT-BUTYL-O-BENZOQUINONE (DTBQ) is a quinone derivative formed through the oxygen transfer reaction from the peroxy anion of N5-ethyl-4a-hydroperoxy-3-methyllumiflavin (4a-FlEtO2-) to the 3,5-di-tert-butylcatechol anion. This reaction highlights its role as an oxidation product in biomimetic flavoenzyme dioxygenase processes, demonstrating the efficient transfer of oxygen atoms facilitated by the flavin intermediate. The formation of DTBQ underscores its significance in studying oxygen transfer mechanisms and reactive intermediates in chemical and biochemical systems.

Technology Process of 3,5-Di-tert-butyl-o-benzoquinone

There total 153 articles about 3,5-Di-tert-butyl-o-benzoquinone 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: 89.0%

2,4-di-tert-Butylphenol (96-76-4) → 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol (6390-69-8) + 3,5-di-tert-butyl-o-benzoquinone (3383-21-9)

Guidance literature:

(2+) (tip:tetraimidazolylmethyl-substituted pyridine ligands); In nitromethane; for 24h; Ambient temperature;

DOI:10.1246/bcsj.64.165

Reference yield: 61.0%

3,5-Di-tert-butylcatechol (1020-31-1,122983-47-5,881376-69-8) → 3,5-di-tert-butyl-muconic acid anhydride (24289-60-9) + 2,4-di-tert-butyl muconolactone (22802-86-4) + 3-tert-butylfuran-2,5-dione (18261-07-9) + 3,5-di-tert-butyl-o-benzoquinone (3383-21-9)

Guidance literature:

With water; oxygen; iron(III) chloride; In tetrahydrofuran; at 25 ℃; for 24h; under 760 Torr;

DOI:10.1246/cl.1987.719

Reference yield: 52.0%

3,5-Di-tert-butylcatechol (1020-31-1,122983-47-5,881376-69-8) → 2,4-di-tert-butyl muconolactone (22802-86-4) + 3-tert-butylfuran-2,5-dione (18261-07-9) + 3,5-di-tert-butyl-o-benzoquinone (3383-21-9) + 3,5-di-tert-butyl-5-(formyl)-2-furanone (87221-87-2)

Guidance literature:

With pyridine; 1,1'-bipyridyl; oxygen; iron(III) chloride; In tetrahydrofuran; at 25 ℃; for 24h; under 760 Torr; Further byproducts given;

DOI:10.1246/cl.1987.719

upstream raw materials:

3,5-Di-tert-butylcatechol

2,4,6-tri-t-butyl-4-nitrocyclohexa-2,5-dien-1-one

2-methoxy-4,6-di-tert-butylphenol

methanol

Downstream raw materials:

2,3,5-triacetoxy-tert-butylbenzene

3,5-di-tert-butyl-o-benzosemiquinone radical anion

3,5-di-tert-butylcatechol radical

2,4,6-trimethylpyrylium tetrafluoroborate

Refernces

Dioxygen Transfer from 4a-Hydroperoxyflavin Anion. 2. Oxygen Transfer to the 10 Position of 9-Hydroxyphenanthrene Anions and to 3,5-Di-tert-butylcatechol Anion

10.1021/ja00533a028

The research investigates the reaction mechanisms of oxygen transfer from the peroxy anion of N5-ethyl-4a-hydroperoxy-3-methyllumiflavin (4a-FlEtO2-) to various phenolate anions, aiming to understand the underlying processes and provide insights into biomimetic reactions of flavoenzyme dioxygenase. The study found that 4a-FlEtO2- can transfer both oxygen atoms to phenolate anions, leading to the formation of specific products and regeneration of reduced flavin. Key chemicals involved include 4a-FlEtO2-, phenolate anions such as 3,5-di-tert-butylcatechol (VIII), 10-methyl-9-phenanthrol (Ib), and 10-ethoxy-9-phenanthrol (Ia), and their respective products like 3,5-di-tert-butyl-o-quinone (IX), 10-hydroxy-10-methyl-9,10-dihydro-9-phenanthrone (IIIb), and 9,10-phenanthrenequinone (V). The research concludes that the oxygen-donating intermediate formed from 4a-FlEtO2- is likely a dioxetane or an oxygen molecule loosely associated with the flavin, and the reaction efficiency of 4a-FlEtO2- exceeds that of molecular oxygen by a significant margin, indicating a unique and efficient oxygen transfer mechanism.