172170-94-4

Basic information

• Product Name: (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL
• Synonyms: (S)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL;(R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL;6,6'-Dimethyl-1,1'-bi-2-naphthol
• CAS NO: 172170-94-4
• Molecular Formula: C22H18O2
• Molecular Weight: 314.38
• Mol File: 172170-94-4.mol
• Article Data: 3

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(172170-94-4)
• EPA Substance Registry System: (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL(172170-94-4)

Safety Data

• Hazardous Substances Data: 172170-94-4(Hazardous Substances Data)

Usage

General Description

(R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL is a chemical compound that belongs to the class of biaryl compounds. It is a chiral molecule, meaning it has a non-superimposable mirror image. (R)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL is commonly used as a chiral ligand in asymmetric catalysis and organic synthesis. It is known for its ability to catalyze a variety of reactions with high enantioselectivity, making it an important tool in the production of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and reactivity make it a valuable tool in the field of organic chemistry.

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.].

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.