172877-00-8

Basic information

• Product Name: (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL
• Synonyms: (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL;(S)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL
• CAS NO: 172877-00-8
• Molecular Formula: C22H18O2
• Molecular Weight: 314.38
• Mol File: 172877-00-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL(172877-00-8)
• EPA Substance Registry System: (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL(172877-00-8)

Safety Data

• Hazardous Substances Data: 172877-00-8(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Synthesis:
(R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL is used as a chiral ligand in asymmetric synthesis, particularly for catalytic asymmetric epoxidation reactions. Its ability to selectively interact with other molecules makes it a crucial component in the production of enantiomerically pure compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL is used as a key intermediate in the synthesis of various drugs. Its chiral properties enable the creation of drugs with specific stereochemistry, which can be essential for their efficacy and safety.
Used in Agrochemical Industry:
(R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL also finds applications in the agrochemical industry, where it is utilized in the development of chiral pesticides and other agrochemical products. (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL's ability to influence the stereochemistry of chemical reactions is crucial for creating effective and targeted products.
Used in Materials Science:
In the field of materials science, (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL is used to develop new materials with specific properties. Its chiral nature allows for the creation of materials with unique characteristics, such as improved optical, electronic, or mechanical properties, depending on the desired application.

Upstream product

• 17579-79-2 2-methyl-6-hydroxynaphthalene 
• 7647-01-0 hydrogenchloride 
• 7705-08-0 iron(III) chloride 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 79082-80-7 (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol 
• 74-88-4 methyl iodide 

Relevant articles and documents

Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones

Privileged biaryl frameworks, BINOL and NOBIN, were efficiently constructed with sole 1-DNQs as arylation reagents under one set of reaction conditions. The judicious selection of palladium-catalytic system plays a pivotal role in the excellent selectivities. This transformation accommodated fairly broad substrate generality for both 2-naphthol and N-Boc-2-naphthylamine and afforded the structurally diversified BINOLs and NOBIN derivatives in high efficiency. Notably, the bromo-substituents which cannot survive in conventional palladium-catalyzed reactions were well-compatible with this set of conditions, providing an effective handle for further enriching the library of BINOLs and NOBINs. Preliminary attempts on the asymmetric variant of this reaction were also performed with up to 80:20 er for BINOLs synthesis. [Figure not available: see fulltext.].

Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes

Novel chiral iron phosphate complexes were prepared as catalysts for asymmetric oxidative coupling reactions. These catalysts were applied for the synthesis of enantio-enriched C1- and C2-symmetric BINOLs, in which the 3 and 3′ positions are available for chemical modifications. It was proposed that the reaction takes place via an oxidative radical-anion coupling mechanism. A destructive BINOL racemization that competes with the enantioselective oxidative coupling of 2-naphthols was revealed, thereby offering new insights into this highly important reaction.

Protecting group free synthesis of 6-substituted naphthols and binols

A straightforward route for the preparation of 6-substituted naphthols and 6,6′-disubstituted binols (binol = 2,2′-dihydroxy-1,1′- binaphthyl) is presented. The synthesis has been accomplished by a one-step procedure starting from 6-bromo derivatives via direct lithiation with n-BuLi, followed by the addition of several electrophiles. This C-C functionalization has been successfully achieved with iodomethane, 3-methoxybenzaldehyde, benzophenone, methyl-2-methylbenzoate, methylbenzoate, dimethyl carbonate, ethyl 2-chloro-2-oxoacetate, and 2,2-dimethyloxirane (E). This reactivity offers a useful protecting group free synthetic protocol, toward chiral disubstituted 6,6′-binols with configuration retention of the binol moiety.