Phenol, 4,4'-dithiobis[2,6-bis(1,1-dimethylethyl)-

Base Information

• Chemical Name: Phenol, 4,4'-dithiobis[2,6-bis(1,1-dimethylethyl)-
• CAS No.: 6386-58-9
• Molecular Formula: C28H42O2S2
• Molecular Weight: 474.772
• UNII: F2ZUM2VQ6P
• DSSTox Substance ID: DTXSID60364473
• Nikkaji Number: J60.272H
• Wikidata: Q65653421
• Mol file: 6386-58-9.mol

Synonyms:6386-58-9;Phenol, 4,4'-dithiobis[2,6-bis(1,1-dimethylethyl)-;F2ZUM2VQ6P;2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxyphenyl)disulfanyl]phenol;UNII-F2ZUM2VQ6P;4,4'-(Disulfanediyl)bis(2,6-di-tert-butylphenol;bis(3,5-di-tert-butyl-4-hydroxyphenyl) disulfide;4,4'-Dithiobis(2,6-bis(1,1-dimethylethyl)phenol;Phenol, 4,4'-dithiobis(2,6-bis(1,1-dimethylethyl)-;2,6-Ditert-butyl-4-((3,5-ditert-butyl-4-hydroxyphenyl)disulfanyl)phenol;4,4'-(Disulfanediyl)bis(2,6-di-tert-butylphenol);Bis(3,5-di-tert-butylphen-4-ol) Disulfide;Probucol Related Compound B;SCHEMBL1116345;DTXSID60364473;AKOS002346711;4,4'-dithiobis(2,6-di-t-butylphenol);4,4'-dithiobis(2,6-di-tert-butylphenol);4,4'-Dithio-bis(2,6-di-tert-butylphenol);bis(3,5-ditertiary-butyl-4-hydroxyphenyl)disulfide;Q65653421;Phenol, 4,4/'-dithiobis[2,6-bis(1,1-dimethylethyl)-

Chemical Property of Phenol, 4,4'-dithiobis[2,6-bis(1,1-dimethylethyl)-

Chemical Property:

• PSA: 91.06000
• LogP: 9.08720
• XLogP3: 10
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 474.26262293
• Heavy Atom Count: 32
• Complexity: 503

Purity/Quality:

95% ^*data from raw suppliers

Bis(3,5-di-tert-butylphen-4-ol)Disulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)SSC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C
• Uses: Bis(3,5-di-tert-butylphen-4-ol) Disulfide is a related compound to Probucol (P755100), an antilipemic. Used as an antioxidant in the treatment of atherosclerosis.

Technology Process of Phenol, 4,4'-dithiobis[2,6-bis(1,1-dimethylethyl)-

There total 8 articles about Phenol, 4,4'-dithiobis[2,6-bis(1,1-dimethylethyl)- 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: 30.0%

(4,4'-isopropylidenedithio)bis[2,6-di-tert-butylphenol] (23288-49-5) → 4,4'-dithiobis(2,6-di-tert-butylphenol) (6386-58-9) + bis(4-hydroxy-3,5-di-tert-butylphenyl) trisulfide (6386-61-4) + 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2)

Guidance literature:

With tetraethylammonium perchlorate; In acetonitrile; Electrolysis;

DOI:10.1248/cpb.49.943

Reference yield: 27.0%

1-thiopropane (107-03-9) + 4-hydroxy-3,5-di-tert-butylthiophenol (950-59-4) → 4,4'-dithiobis(2,6-di-tert-butylphenol) (6386-58-9) + 2,6-di-tert-butyl-4-(propyldisulfanyl)-phenol + Dipropyl disulfide (629-19-6)

Guidance literature:

With 4,6-di-tert-butyl-N-(tert-butyl)-o-aminophenol; In acetonitrile; at 20 ℃; for 4h; Electrochemical reaction;

DOI:10.1149/1945-7111/abfe43

Reference yield: 15.5%

4-hydroxy-3,5-di-tert-butylthiophenol (950-59-4) → 4,4'-dithiobis(2,6-di-tert-butylphenol) (6386-58-9) + bis(4-hydroxy-3,5-di-tert-butylphenyl) trisulfide (6386-61-4) + 4,4'-thiobis[2,6-bis(tert-butyl)phenol] (4673-51-2) + bis(4-hydroxy-3,5-di-tert-butylphenyl) tetrasulfide (31121-17-2) + bis(4-hydroxy-3,5-di-tert-butylphenyl) pentasulfide

Guidance literature:

With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; In isopropyl alcohol; at 150 ℃; for 1h; Product distribution;

upstream raw materials:

3,5-di-tert-butyl-4-hydroxyphenylthiocyanate

4-hydroxy-3,5-di-tert-butylthiophenol

2,6-di-tert-butylphenol

(4,4'-isopropylidenedithio)bis[2,6-di-tert-butylphenol]

Downstream raw materials:

Tetraethyl 3,5-ditertiarybutyl-4-hydroxyphenylthio-methylenediphosphonate

3,5-di-tert-butyl-4-hydroxyphenyl S-(hydroxymethyl) sulfide

3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-thiopropionic acid S-(3,5-di-tert-butyl-4-hydroxy-phenyl) ester

S-(3,5-di-tert-butyl-4-hydroxyphenyl)-O,O-diphenyl phosphorothiolate

Refernces

• 1、 Berberova, Nadezhda T.,Burmistrova, Daria A.,Galustyan, Andrey,Smolyaninov, Ivan V.. "Substituted o-Aminophenols as Redox-Mediators in the Thiol Oxidation to Unsymmetrical Disulfides". . . Retrieved 2021/06/17.
• 2、 Bukharov, S. V.,Konoshenko, L. V.,Solov'eva, S. E.,Syakaev, V. V.,Chugunov, Yu. V.,Samuilov, Ya. D.. "Reaction of 2,6-Di-tert-butylphenol with Sulfur in Dimethylformamide in the Presence of Oxygen". . p. 667 - 669. Retrieved 2007/10/03.