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

• 74292-07-2 C₅₀H₄₄O₆*C₈H₉NO₂*ClHO₄ 
• 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 
• 57585-09-8 methyl 4-phenylpenta-2,3-dienoate 
• 57585-10-1 4-phenyl-2,3-hexadienoic acid methyl ester 
• 55442-39-2 Dimethyl-ditosylat 25d' 
• 149733-66-4 (R*,R*)-(MeC₁₀H₅O)2W(CHPh) 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 1220514-89-5 C₅₇H₅₄O₃P₂ 
• 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 
• 201732-49-2 C₃₈H₃₄NO₂P 

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.

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.