55515-99-6

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;(1S)-3,3'-diMethyl-1,1'-Binaphthalene]-2,2'-diol;(S)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 99%e.e.;(1S)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 95% (99% ee)
• CAS NO: 55515-99-6
• Molecular Formula: C₂₂H₁₈O₂
• Molecular Weight: 314.38
• Mol File: 55515-99-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 203-204 °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(55515-99-6)
• EPA Substance Registry System: (R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL(55515-99-6)

Safety Data

• Hazardous Substances Data: 55515-99-6(Hazardous Substances Data)

Usage

General Description

"(R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL, also known as (R)-BINOL, is a well-known chemical compound frequently used as a chiral ligand in the field of synthetic chemistry. It is a white crystalline powder and is soluble in several organic solvents but insoluble in water. Its formula is C22H18O2 and its molecular weight is 322.37 g/mol. The compound is a derivative of 1,1'-binaphthyl and it has been acknowledged for its usefulness in the creation of a variety of catalytic, chiral chemical reactions, particularly in enantioselective synthesis. Its (R) enantiomer configuration denotes the direction of its molecular rotation. Despite being generally stable, it should be stored away from heat, spark, or open flames.

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 
• 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 
• 55442-34-7 3,3'-dimethyl-1,1'-binaphthalene-2,2'-diol 
• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 

Downstream Products

• 55515-98-5 (R)-3,3'-dimethyl-1,1'-binaphthalene-2,2'-diol 
• 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 
• 55442-39-2 Dimethyl-ditosylat 25d' 
• 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 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 149733-66-4 (R*,R*)-(MeC₁₀H₅O)2W(CHPh) 
• 57585-10-1 4-phenyl-2,3-hexadienoic acid methyl ester 
• 57585-09-8 methyl 4-phenylpenta-2,3-dienoate 
• 74292-07-2 C₅₀H₄₄O₆*C₈H₉NO₂*ClHO₄ 

Relevant articles and documents

Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl-based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2) was used. Additionally, one-pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields.

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.