(S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL

Base Information

• Chemical Name: (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL
• CAS No.: 101203-31-0
• Molecular Formula: C24H34 O2
• Molecular Weight: 354.533
• Mol file: 101203-31-0.mol

Synonyms:2,2'-Bi-3,4-xylenol,6,6'-di-tert-butyl- (7CI);3,3'-Di-tert-butyl-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diol;3,3'-Di-tert-butyl-5,5',6,6'-tetramethylbiphenyl-2,2'-diol;

Chemical Property of (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL

Chemical Property:

• Vapor Pressure: 1.12E-07mmHg at 25°C
• Melting Point: 170-174 °C
• Refractive Index: 1.545
• Boiling Point: 420.8°Cat760mmHg
• PKA: 10.95±0.50(Predicted)
• Flash Point: 173.5°C
• PSA: 40.46000
• Density: 1.012g/cm³
• LogP: 6.59340
• Storage Temp.: 2-8°C

Purity/Quality:

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

racemic-5,5',6,6'-Tetramethyl-3,3'-di-t-butyl-1,1'-biphenyl-2,2'-diol, 99% rac-BIPHEN H2 ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Cocatalyst in titanium-catalyzed intermolecular hydroaminationReactant in preparation of:Sulfonate phenol ligands via sulfonylationCatalysts for asymmetric olefin hydroamination/cyclization reactionsSingle site catalyst precursors for catalysis of ring-opening reactionsBiphen-Mo complex used for catalysis of enantioselective ring-closing metathesis

Technology Process of (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL

There total 7 articles about (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-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: 85.0%

2-(1,1-dimethylethyl)-4,5-dimethylphenol (1445-23-4) → 3,3'-di-tert-butyl-5,5',6,6'-tetramethylbiphenyl-2,2'-diol (101203-31-0)

Guidance literature:

With N,N'-ethylenebis(3,5-tert-butylsalicylideneiminato)(nitrito)(chloro)ruthenium; oxygen; In 1,2-dichloro-ethane; at 80 ℃; for 72h; Inert atmosphere;

DOI:10.1021/ja500183z

Reference yield: 30.0%

sodium[tetrakis(2-tert-butyl-4,5-dimethylphenoxy)borate] → 3,3'-di-tert-butyl-5,5',6,6'-tetramethylbiphenyl-2,2'-diol (101203-31-0)

Guidance literature:

sodium[tetrakis(2-tert-butyl-4,5-dimethylphenoxy)borate]; In acetonitrile; at 40 ℃; Electrolysis;

With citric acid; In water; acetonitrile; for 0.0833333h;

DOI:10.1002/chem.200600375

Reference yield:

rac-3,3'-bis(tert-butyl)-5,5'6,6'-tetramethyl-1,1'-binphenyl-2,2'-dihydrogenphosphoric acid → 3,3'-di-tert-butyl-5,5',6,6'-tetramethylbiphenyl-2,2'-diol (101203-31-0)

Guidance literature:

With hydrogenchloride; sodium hydrogencarbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; dimethyl sulfate;

DOI:10.1021/ja974353i

upstream raw materials:

2-(1,1-dimethylethyl)-4,5-dimethylphenol

4-t-butyl-o-xylene

3,4-Dimethylphenol

Downstream raw materials:

Mo(1-phenylcyclohexylimido)(CHCMe₂Ph)[(S)-3,3'-di-tert-butyl-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diolate)]

Refernces

• 1、 Alexander,La,Cefalo,Hoveyda,Schrock. "Catalytic enantioselective ring-closing metathesis by a chiral biphen- Mo complex [14]". . p. 4041 - 4042. Retrieved 1998.
• 2、 Niederer, Kyle A.,Gilmartin, Philip H.,Kozlowski, Marisa C.. "Oxidative photocatalytic homo- And cross-coupling of phenols: Nonenzymatic, catalytic method for coupling tyrosine". . p. 14615 - 14623. Retrieved 2020/12/23.