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

• 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 
• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 55442-34-7 3,3'-dimethyl-1,1'-binaphthalene-2,2'-diol 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 42167-06-6 3,3'-bis(hydroxymethyl)-2,2'-dihydroxy-1,1'-binaphthyl 
• 602-09-5 1,1'-bi-2-naphthol 
• 345648-05-7 3,3'-dimethyl-2,2'-dimethoxy-1,1'-dinaphthyl 
• 55442-33-6 3,3'-bis(bromomethyl)-2,2'-dihydroxy-1,1'-binaphthyl 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 74-88-4 methyl iodide 
• 142010-89-7 3,3'-Dimethyl-2,2'-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,1']binaphthalenyl 

Downstream Products

• 39648-71-0 3,3’-dimethyl-[1,1’-binaphthalene]-2,2’-diol 
• 57585-09-8 methyl 4-phenylpenta-2,3-dienoate 
• 57585-10-1 4-phenyl-2,3-hexadienoic acid methyl ester 
• 201732-49-2 C₃₈H₃₄NO₂P 
• 201732-49-2 (2,6-dimethyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 
• 1220514-89-5 C₅₇H₅₄O₃P₂ 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 

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.

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.