55515-98-5

Basic information

• Product Name: (R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL
• Synonyms: (R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL;(S)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL;3,3'-Dimethyl-1,1'-binaphthalene-2-2'-diol;(1R)-3,3'-diMethyl-1,1'-Binaphthalene]-2,2'-diol;(R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 99%e.e.;(1R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 98% (99% ee)
• CAS NO: 55515-98-5
• Molecular Formula: C₂₂H₁₈O₂
• Molecular Weight: 314.38
• Mol File: 55515-98-5.mol
• Article Data: 30

Chemical Properties

• Melting Point: 201-202 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• Boiling Point: 461.2±40.0 °C(Predicted)
• Appearance: /
• Density: 1.245±0.06 g/cm3(Predicted)
• PKA: 8.61±0.50(Predicted)
• CAS DataBase Reference: (R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL(55515-98-5)
• EPA Substance Registry System: (R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL(55515-98-5)

Safety Data

• Hazardous Substances Data: 55515-98-5(Hazardous Substances Data)

Usage

General Description

(R)-3,3'-Dimethyl-1,1'-binaphthyl-2,2'-diol (DMBINOL) is a chiral organic compound with a binaphthyl backbone. It is widely used as a chiral auxiliary in asymmetric synthesis, particularly in the preparation of chiral ligands for transition metal-catalyzed reactions. DMBINOL is known for its ability to facilitate enantioselective transformations and has been employed in the production of pharmaceuticals, agrochemicals, and fine chemicals. Its unique structural characteristics make it a valuable tool in the field of asymmetric synthesis, and its use continues to expand in various industrial and academic applications.

Upstream product

• 55442-33-6 3,3'-bis(bromomethyl)-2,2'-dihydroxy-1,1'-binaphthyl 
• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 17324-04-8 3-methyl-naphthalen-2-ol 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 77-78-1 dimethyl sulfate 
• 345648-05-7 3,3'-dimethyl-2,2'-dimethoxy-1,1'-dinaphthyl 
• 602-09-5 1,1'-bi-2-naphthol 
• 42167-06-6 3,3'-bis(hydroxymethyl)-2,2'-dihydroxy-1,1'-binaphthyl 
• 55442-34-7 3,3'-dimethyl-1,1'-binaphthalene-2,2'-diol 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 65355-11-5 (Sa)-3,3'-dimethyl-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 142010-89-7 3,3'-Dimethyl-2,2'-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,1']binaphthalenyl 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 74-88-4 methyl iodide 

Downstream Products

• 74292-07-2 C₅₀H₄₄O₆*C₈H₉NO₂*ClHO₄ 
• 39648-71-0 3,3’-dimethyl-[1,1’-binaphthalene]-2,2’-diol 
• 201732-49-2 ((P)-bis-3,3'-dimethyl-naphthaleno[1,2-f;2,1-d]-1,3-dioxa-2-phosphacycloheptan-2-yl)-(R,R)-bis(1-phenylethyl)amine 
• 201732-49-2 ((M)-bis-3,3'-dimethyl-naphthaleno[1,2-f;2,1-d]-1,3-dioxa-2-phosphacycloheptan-2-yl)-(R,R)-bis(1-phenylethyl)amine 
• 57585-09-8 methyl 4-phenylpenta-2,3-dienoate 
• 57585-10-1 4-phenyl-2,3-hexadienoic acid methyl ester 

Relevant articles and documents

Chiral Selenide/Achiral Sulfonic Acid Cocatalyzed Atroposelective Sulfenylation of Biaryl Phenols via a Desymmetrization/Kinetic Resolution Sequence

Enantioselective synthesis of axially chiral sulfur-containing biaryl derivatives through the electrophilic sulfenylation of biaryl phenols has been achieved for the first time. This catalytic asymmetric system, which involves sequential desymmetrization and kinetic resolution, is enabled by a combination of a novel 3,3′-disubstituted BINOL-derived selenide catalyst and an achiral sulfonic acid. Control experiments and computational studies suggest that multiple noncovalent interactions between the cocatalysts and substrate, especially a network of hydrogen bond interactions, play a crucial role in determining the enantioselectivity and reactivity.

An enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide-iron(ii) complexes

An enantioselective oxidative coupling of 2-naphthol derivatives is developed with the use of chiral Fe(ii)-diphosphine oxide complexes. Optically active 1,1-bi-2-naphthol derivatives can be synthesized in high yields when a 2?:?1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is used in the presence of t-butyl hydroperoxide as an oxidant. The non-linear effect, X-ray crystal structure and ESI-MS suggest that a 2?:?1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is a pre-catalyst for a Fe(iii)/Fe(iv) redox cycle.

Photochemical Oxidative Coupling of 2-Naphthols using a Hybrid Reduced Graphene Oxide/Manganese Dioxide Nanocomposite under Visible-Light Irradiation

We describe a simple, cost-effective, efficient, and high-yielding photocatalytic approach for the oxidative self-dimerization of 2-naphthols using a semiconductor–metal hybrid that consists of intercalated manganese dioxide nanoparticles in reduced graphene oxide (rGO/MnO2) under visible-light irradiation. The desired photocatalyst was synthesized in a single step by mixing MnO2 nanoparticles with rGO ultrasonically. The hybrid photocatalyst exhibited a significantly higher activity than neat MnO2 nanoparticles and rGO, which is believed to be because of the synergistic effect of its components. To our knowledge, this hybrid rGO/MnO2 nanocomposite is the first heterogeneous, green photocatalyst for the oxidative coupling of 2-naphthols under mild conditions.