3,3',5,5'-Tetra-tert-butylbiphenyl-2,2'-diol

Base Information

• Chemical Name: 3,3',5,5'-Tetra-tert-butylbiphenyl-2,2'-diol
• CAS No.: 6390-69-8
• Deprecated CAS: 149419-42-1
• Molecular Formula: C28H42O2
• Molecular Weight: 410.64
• Hs Code.: 2907299090
• European Community (EC) Number: 407-920-5,622-154-3
• NSC Number: 122714
• UNII: L9W97XDT3C
• DSSTox Substance ID: DTXSID10884292
• Nikkaji Number: J336.947A
• Wikidata: Q27282888
• Mol file: 6390-69-8.mol

Synonyms:2,2'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl;2,2-DTTBB

Chemical Property of 3,3',5,5'-Tetra-tert-butylbiphenyl-2,2'-diol

Chemical Property:

• Vapor Pressure: 0-11Pa at 25-141℃
• Melting Point: 194-195℃
• Boiling Point: 469.3 °C at 760 mmHg
• PKA: 10.76±0.48(Predicted)
• Flash Point: 186.8 °C
• PSA: 40.46000
• Density: 0.981 g/cm³
• LogP: 7.95480
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 9.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 410.318480578
• Heavy Atom Count: 30
• Complexity: 513

Purity/Quality:

99.9% ^*data from raw suppliers

3,3'',5,5''-Tetra-tert-butyl-2,2''-dihydroxybiphenyl ^*data from reagent suppliers

Safty Information:

• Statements: 53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=C(C(=C1)C(C)(C)C)O)C2=C(C(=CC(=C2)C(C)(C)C)C(C)(C)C)O
• Uses: 3,3'',5,5''-Tetra-tert-butyl-2,2''-dihydroxybiphenyl is used in the Kolbe-Schmitt synthesis of pharmacologically useful salicylates.

Technology Process of 3,3',5,5'-Tetra-tert-butylbiphenyl-2,2'-diol

There total 53 articles about 3,3',5,5'-Tetra-tert-butylbiphenyl-2,2'-diol 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%

2,4-di-tert-Butylphenol (96-76-4) → 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol (6390-69-8)

Guidance literature:

With C₂₄H₁₃Cu₂F₉N₄O₇; oxygen; In isopropyl alcohol; at 90 ℃; for 12h; under 760.051 Torr;

DOI:10.1039/c1dt11065a

Reference yield: 95.0%

6,6'-bis<2,4-di-tert-butyl-6-chlorocyclohexa-2,4-dien-1-one> (78231-91-1) → 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol (6390-69-8)

Guidance literature:

Raney Ni (W-2); In ethanol; at 50 ℃; for 0.5h;

DOI:10.1021/jo00332a004

Reference yield: 95.0%

2,4-di-tert-butyl-6-((dicyclohexylamino)methyl)phenol → 3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol (6390-69-8)

Guidance literature:

With manganese triacetate; In acetic acid; for 2h;

DOI:10.1007/BF02495927

upstream raw materials:

carbon dioxide

potassium 2,4-di-tert-butylphenolate

2,4-di-tert-Butylphenol

2,4,6-tri-tert-butylphenoxol

Downstream raw materials:

1-bromo-2-ethoxy-4,6,8-tri-tert-butyldibenzofuran

3,3'-bis(1,1-dimethylethyl)-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine>

3,3',5,5'-tetra-tert-butyl-2-<(2,4,8,10-tetra-tert-butyl-12H-dibenzo<1,3,2>dioxaphosphepin-6-yl)oxy>-2'-hydroxy-1,1'-biphenyl

3,3'-dimethyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine>

Refernces

• 1、 Materne, Karolin,Braun-Cula, Beatrice,Herwig, Christian,Frank, Nicolas,Limberg, Christian. "Bismuthanes as Hemilabile Donors in an O2-Activating Palladium(0) Complex". . p. 11797 - 11801. Retrieved 2017.
• 2、 Li, Wei,Song, Feijie,You, Jingsong. "Oxidant-Controlled Catalytic Transformations of Phenols with Unexpected Cleavage of Aromatic Rings". . p. 13913 - 13918. Retrieved 2015.
• 3、 Morimoto, Yuma,Takagi, Yusaku,Saito, Toru,Ohta, Takehiro,Ogura, Takashi,Tohnai, Norimitsu,Nakano, Motohiro,Itoh, Shinobu. "A Bis(μ-oxido)dinickel(III) Complex with a Triplet Ground State". . p. 7640 - 7643. Retrieved 2018.
• 4、 Li,Braun-Cula,Hoof,Limberg. "Copper(i) complexes based on ligand systems with two different binding sites: Synthesis, structures and reaction with O2". . p. 544 - 560. Retrieved 2018.
• 5、 Kushioka, Keiko,Tanimoto, Iwao,Maruyama, Kazuhiro. "Oxidation of 2,4-Di-t-butylphenol with Hydrogen Peroxide Catalyzed by Bis(ethylenediamine)copper(II) Complex". . p. 1147 - 1153. Retrieved 1989.
• 6、 Zaragoza, Jan Paulo T.,Siegler, Maxime A.,Goldberg, David P.. "A Reactive Manganese(IV)-Hydroxide Complex: A Missing Intermediate in Hydrogen Atom Transfer by High-Valent Metal-Oxo Porphyrinoid Compounds". . p. 4380 - 4390. Retrieved 2018.
• 7、 Straub, Bernd F.,Wrede, Michael,Schmid, Karin,Rominger, Frank. "A lipophilic, fluorine-free, thermostable, inexpensive, S 4-Symmetric, highly soluble, weakly coordinating, protolabile aluminate". . p. 1907 - 1911. Retrieved 2010.
• 8、 Pálv?lgyi, ádám Márk,Smith, Jakob,Schnürch, Michael,Bica-Schr?der, Katharina. "Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids". . p. 850 - 860. Retrieved 2021/01/09.
• 9、 -. "Method for synthesizing bisphosphite". Paragraph 0069; 0071; 0075; 0076. . Retrieved 2020/06/02.