101203-31-0

Basic information

• Product Name: (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL
• Synonyms: (S) BIPHEN H2;(S)-(-)-BIPHEN H2;(R) BIPHEN H2;(R)-(+)-BIPHEN H2;(S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL;(S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-T-BUTYL-1,1'-BIPHENYL-2,2'-DIOL;(S)-(-)-3,3'-DI-T-BUTYL-5,5',6,6'-TETRAMETHYL-1,1'-BIPHENYL-2,2'-DIOL;(R)-(+)-5,5',6,6'-TETRAMETHYL-3,3'-DI-T-BUTYL-1,1'-BIPHENYL-2,2'-DIOL
• CAS NO: 101203-31-0
• Molecular Formula: C₂₄H₃₄O₂
• Molecular Weight: 354.53
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis;Other Ligands;BIPHEN Series;Achiral Oxygen
• Mol File: 101203-31-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 170-174 °C
• Boiling Point: 420.8°Cat760mmHg
• Flash Point: 173.5°C
• Appearance: white to off-white/crystal
• Density: 1.012g/cm³
• Vapor Pressure: 1.12E-07mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: 2-8°C
• PKA: 10.95±0.50(Predicted)
• CAS DataBase Reference: (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL(101203-31-0)
• EPA Substance Registry System: (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL(101203-31-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 101203-31-0(Hazardous Substances Data)

Usage

Description

(S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL is a complex organic compound with a unique molecular structure that features two biphenyl rings connected by two hydroxyl groups. It is characterized by the presence of four methyl groups and two tert-butyl groups, which contribute to its stability and reactivity. (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL has found applications in various chemical reactions and processes, making it a valuable component in the field of organic chemistry.

Uses

Used in Catalyst Synthesis:
(S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL is used as a cocatalyst in titanium-catalyzed intermolecular hydroamination reactions. Its unique structure allows it to facilitate the reaction process, leading to the formation of desired products with improved yields and selectivity.
Used in Ligand Preparation:
In the field of asymmetric catalysis, (S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL serves as a reactant in the preparation of sulfonate phenol ligands via sulfonylation. These ligands are crucial for the development of efficient and selective catalysts for various organic transformations.
Used in Catalyst Development:
(S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL is utilized in the development of catalysts for asymmetric olefin hydroamination/cyclization reactions. Its presence in the catalyst structure enhances the enantioselectivity and reactivity of the catalyst, enabling the synthesis of chiral compounds with high enantiomeric excess.
Used in Single Site Catalyst Precursors:
(S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL also serves as a precursor for single site catalysts used in the catalysis of ring-opening reactions. Its unique structure allows for the design of highly active and selective catalysts that can efficiently convert various substrates into valuable products.
Used in Biphen-Mo Complex Synthesis:
(S)-(-)-5,5',6,6'-TETRAMETHYL-3,3'-DI-TERT-BUTYL-1,1'-BIPHENYL-2,2'-DIOL is employed in the synthesis of a Biphen-Mo complex, which is used for the catalysis of enantioselective ring-closing metathesis reactions. This complex allows for the formation of cyclic compounds with high enantiomeric purity, making it a valuable tool in the synthesis of biologically active molecules and pharmaceuticals.

Reaction

Used as a ligand backbone for metathesis catalysts. ?2. Used as a ligand backbone in catalytic asymmetric hydrogenation. ?3. Used as a ligand backbone for asymmetric hydroformylation of allyl cyanide. ?4. Used as a ligand backbone for phosphoramidite ligands in the asymmetric ?Rh-catalyzed [2+2+2] cycloaddition. ?5. Used as a ligand backbone for the ring-opening polymerization of cyclic esters.

InChI:InChI=1/C24H34O2/c1-13-11-17(23(5,6)7)21(25)19(15(13)3)20-16(4)14(2)12-18(22(20)26)24(8,9)10/h11-12,25-26H,1-10H3

Upstream product

• 1445-23-4 2-(1,1-dimethylethyl)-4,5-dimethylphenol 
• 7397-06-0 4-t-butyl-o-xylene 
• 95-65-8 3,4-Dimethylphenol 

Downstream Products

• 874911-38-3 2,2'-(3,3',4,4'-tetramethyl-6,6'-di-tert-butyl)biphenyl 3-(N,N-dimethylamino)phenyl phosphite 
• 214264-65-0 [molybdenum(dimethylphenylimido)(CHC(CH₃)2C₆H₅)(OC₆H(CH₃)2C(CH₃)3)2] 
• 205815-80-1 [molybdenum(diisopropylphenylimido)(CHC(CH₃)2C₆H₅)(OC₆H(CH₃)2C(CH₃)3)2] 
• 205815-80-1 (2,6-diisopropylphenylimide){3,3′-di(t-butyl)-5,5′,6,6′-tetramethyl-2,2′-biphenoxy}neophylidenemolybdenum(VI) 
• 929212-06-6 Mo(1-phenylcyclohexylimido)(CHCMe₂Ph)[(S)-3,3'-di-tert-butyl-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diolate)] 

Relevant articles and documents

Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights

The evolution of a more reactive chiral vanadium catalyst for enantioselective oxidative coupling of phenols is reported, ultimately resulting in a simple monomeric vanadium species combined with a Br?nsted or Lewis acid additive. The resultant vanadium complex is found to effect the asymmetric oxidative ortho-ortho coupling of simple phenols and 2-hydroxycarbazoles with good to excellent levels of enantioselectivity. Experimental and quantum mechanical studies of the mechanism indicate that the additives aggregate the vanadium monomers. In addition, a singlet to triplet crossover is implicated prior to carbon-carbon bond formation. The two lowest energy diastereomeric transition states leading to the enantiomeric products differ substantially with the path to the minor enantiomer involving greater torsional strain between the two phenol moieties.

Visible-Light-Driven di-t-Butyl Peroxide-Promoted the Oxidative Homo- and Cross-Coupling of Phenols

The visible-light-induced oxidative homo- and cross-coupling of phenols by di-t-butyl peroxide (DTBP) are described. These reactions occur with metal-free process and feature high chemo- and regioselectivity under mild reaction conditions. DTBP is an inexpensive, benign, stable at room temperature, and commercially available oxidizer. It can be irradiated by blue LEDs to generate tert-butoxyl radical (tBuO?), which induces the oxidative homo-coupling of phenols and the cross-coupling of phenols with naphthols, respectively.

Method for preparing 2-hydroxy-4-methyltetrahydropyran

The invention relates to a method for preparing 2-hydroxy-4-methyltetrahydropyran (MHP) from using 3-methyl-3-buten-1-ol (IPEA) as a raw material under the catalysis of a rhodium compound and a tertiary phosphine ligand. After a reaction is finished, water extraction is performed for separating products from catalysts, wherein the rhodium catalyst and the tertiary phosphine ligand are reserved in an organic phase, the products are reserved in an aqueous phase, the conversion rate of IPEA can be as high as 99.7%, and the MHP selectivity of the products can be up tp 85.9%. The method solves the difficult problem that the costly rhodium catalyst is difficult to recover in a hydroformylation reaction process, and is favorable for industrial application.