215433-51-5

Basic information

• Product Name: R-3-3'-Bis(3,5-bis(methyl)phenyl)-1,1'-bi-2-naphthol
• Synonyms: (R)-3,3'-Bis(3,5-dimethylphenyl)-1,1'-bi-2-naphthalene]-2,2'-diol;(R)-3-3'-Bis(3,5-dimethyl)phenyl-1,1'-bi-2-naphthol, 99%e.e.;R-3-3'-Bis(3,5-bis(methyl)phenyl)-1,1'-bi-2-naphthol;(R)-3,3'-Bis(3,5-dimethylphenyl)-1,1'-bi-2-napthalene]-2,2'-diol;(R)-3-3'-Bis(3,5-dimethylphenyl)-1,1'-bi-2-naphthol;(R)-3-3'-Bis[3,5-bis(methyl)phenyl]-1,1'-bi-2-naphthol, 98% (99% ee)
• CAS NO: 215433-51-5
• Molecular Formula: C36H30O2
• Molecular Weight: 494.64
• Mol File: 215433-51-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 124-125 °C
• Boiling Point: 597.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.190±0.06 g/cm3(Predicted)
• PKA: 8.07±0.50(Predicted)
• CAS DataBase Reference: R-3-3'-Bis(3,5-bis(methyl)phenyl)-1,1'-bi-2-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: R-3-3'-Bis(3,5-bis(methyl)phenyl)-1,1'-bi-2-naphthol(215433-51-5)
• EPA Substance Registry System: R-3-3'-Bis(3,5-bis(methyl)phenyl)-1,1'-bi-2-naphthol(215433-51-5)

Safety Data

• Hazardous Substances Data: 215433-51-5(Hazardous Substances Data)

Usage

General Description

R-3-3'-Bis(3,5-bis(methyl)phenyl)-1,1'-bi-2-naphthol, also known as BINOL, is a chiral molecule used as a ligand in asymmetric catalysis. It is a popular organic compound in the field of organic synthesis and catalysis due to its ability to facilitate enantioselective reactions, particularly in metal-catalyzed processes. BINOL has two naphthol groups that provide chirality, making it an effective ligand for many types of transition metal catalysts. It is widely used in the production of pharmaceuticals, agrochemicals, and fine chemicals, and its versatile applications make it a valuable tool in synthetic chemistry.

Upstream product

• 556-96-7 5-bromo-1,3-xylene 
• 602-09-5 1,1'-bi-2-naphthol 
• 756491-46-0 (+/-)-3,3'-bis(3,5-dimethylphenyl)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 556-97-8 1-chloro-3,5-dimethylbenzene 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 142010-87-5 (±)?3,3'?dibromo?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 30478-88-7 3-bromo-2-naphthol 
• 68251-77-4 2‐bromo‐3‐methoxynaphthalene 
• 93-04-9 2-Methoxynaphthalene 

Relevant articles and documents

A simple synthetic approach to 3,3′-diaryl BINOLs

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Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.

Fast, Efficient and Low E-Factor One-Pot Palladium-Catalyzed Cross-Coupling of (Hetero)Arenes

The homocoupling of aryl halides and the heterocoupling of aryl halides with either aryl bromides or arenes bearing an ortho-lithiation directing group are presented. The use of a Pd catalyst, in combination with t-BuLi, allows for the rapid and efficient formation of a wide range of polyaromatic compounds in a one pot procedure bypassing the need for the separate preformation of an organometallic coupling partner. These polyaromatic structures are obtained in high yields, in 10 min at room temperature, with minimal waste generation (E-factors as low as 1.5) and without the need for strict inert conditions, making this process highly efficient and practical in comparison to classical methods. As illustration, several key intermediates of widely used BINOL-derived structures are readily prepared.