336185-31-0

Basic information

• Product Name: R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol
• Synonyms: R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol;(R)-BIMBOL;(R)-2,2'-Dihydroxy-α,α,α',α'-tetraphenyl-[1,1'- binaphthalene]-3,3'-dimethanol, 99%e.e.;(R)-2,2'-Dihydroxy-α;'-tetraphenyl-[1,1'-binaphthalene]-3,3'-dimethanol, 95% (99% ee)
• CAS NO: 336185-31-0
• Molecular Formula: C46H34O4
• Molecular Weight: 650.75976
• Mol File: 336185-31-0.mol

Chemical Properties

• Boiling Point: 820.1±65.0 °C(Predicted)
• Appearance: /
• Density: 1.297±0.06 g/cm3(Predicted)
• PKA: 8.20±0.50(Predicted)
• CAS DataBase Reference: R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol(CAS DataBase Reference)
• NIST Chemistry Reference: R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol(336185-31-0)
• EPA Substance Registry System: R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol(336185-31-0)

Safety Data

• Hazardous Substances Data: 336185-31-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol serves as a chiral ligand in asymmetric catalysis reactions, which is crucial for the synthesis of enantiomerically pure compounds. This application is vital in the pharmaceutical industry, where the production of single-enantiomer drugs is essential to ensure safety, efficacy, and to avoid potential side effects associated with the unwanted enantiomer.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol is utilized as a chiral ligand to facilitate the synthesis of enantiomerically pure pesticides and other agrochemicals. This ensures that only the desired enantiomer with the intended biological activity is produced, reducing environmental impact and improving the safety and effectiveness of these chemicals.
Used in Fine Chemicals Production:
R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol is also employed in the synthesis of various fine chemicals, which are high-purity chemicals used in a wide range of applications, including fragrances, flavors, dyes, and more. Its chiral properties allow for the creation of specific enantiomers, which can be critical for the desired properties and performance of these fine chemicals.
Used in Material Science:
R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol's unique structure and chiral properties make it a candidate for the development of new materials with specific characteristics, such as optical activity or selectivity in interactions with other molecules. This can lead to advancements in areas like sensors, catalysts, and other specialized materials.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, R-2,2'-dihydroxy-α,α,α',α'-tetraphenyl-[1,1'-Binaphthalene]-3,3'-diMethanol plays a role in the design and synthesis of novel chiral molecules with potential therapeutic applications. Its use in asymmetric catalysis can facilitate the production of new drug candidates with improved pharmacological properties and reduced side effects.

Upstream product

• 602-09-5 1,1'-bi-2-naphthol 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 263744-23-6 Dimethyl 2,2'-bis(methoxymethoxy)-1,1'-binaphthalene-3,3'-dicarboxylate 
• 18531-92-5 (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxylic acid 
• 100-58-3 phenylmagnesium bromide 
• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 55426-75-0 3-(hydroxydiphenylmethyl)naphthalen-2-ol 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 

Relevant articles and documents

Desymmetrization of Symmetrical Triarylcarbinols: Synthesis of 7-Arylfluorenes and a C 2 -Symmetric Chiral BIFOL Phosphoric Acid

A simple and an efficient method for the synthesis of 7-arylfluorenes by intramolecular cyclization of the corresponding triarylcarbinols in the presence of the solid-acid catalyst NaHSO 4 /SiO 2 has been developed. By using this method, a new chiral diol with a C 2 -symmetric bisfluorenyl unit, 7,7′-diphenyl-7 H,7′ H -5,5′-bibenzo[ c ]fluorene-6,6′-diol (BIFOL), having central chirality was synthesized in an optically active form from (S)-(-)-BINOL-3,3′-dicarboxylic acid. The absolute configuration of the chiral bisfluorene derivative BIFOL was ascertained by single-crystal X-ray analysis. Furthermore, a new chiral phosphoric acid was synthesized from BIFOL and evaluated for enantioselective transfer hydrogenation.

Synthesis, characterization and application of some axially chiral binaphthyl phosphoric acids in asymmetric mannich reaction

Two novel chiral Bronsted acids 3b and 3c were prepared without involving the complexity of Suzuki coupling. Catalyst 3c bearing two additional hydroxyl groups at 3 and 3′ positions of axially chiral 1,1-binaphthalene-2,2′-diol phosphoric acid was applied

Enantioselective fluorescent recognition of amino alcohols by a chiral tetrahydroxyl 1,1′-binaphthyl compound

The tetrahydroxyl derivative of BINOL, (S)- or (R)-1, and its analogues are synthesized. (S)- or (R)-1 can be used to conduct the enantioselective recognition of chiral amino alcohols. In comparison with BINOL, the two additional hydroxyl groups of (S)- o

Synthesis of new bifunctional BINOL derivatives

A series of new 3,3′-disubstituted BINOL derivatives have been synthesised. In a preliminary study, the asymmetric induction of these ligands was investigated in the addition of diethyl zinc to benzaldehyde in the absence of Ti(Oi-Pr)4. This showed different enantioselectivity and activity from those of the unsubstituted BINOL.

Enantioselective br?nsted acid catalyzed addition reactions of methyleneaminopyrrolidine to imines

A new series of BINOL-derived multidentate Br?nsted acid catalysts has been developed for the enantioselective addition of the d 1-synthon, methyleneaminopyrrolidine, to N-Boc imines, yielding the versatile, protected α-aminohydrazone intermedi

Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: Efficient formation of chiral functionalized BINOL derivatives

Chiral 1,5-diaza-cis-decalins have been examined as ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol % of a 1,5-diaza-cis-decalin copper(II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3-substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. The relationship between the substitution of the naphthalene starting materials and reactivity/selectivity is determined by several factors which act in concert: (1) the effect of substituents on the oxidation potential of the substrate, (2) the ability of the substrate to participate in a chelated copper complex which depends on (a) the inherent coordinating ability of the 3-substituent and (b) substituent steric interactions that affect chelation between the 2-hydroxyl and 3-substituent, (3) the effect of substituents on dissociation of the product from the copper catalyst.

Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates

(Matrix presented) A series of oxovanadium(IV) complexes derived from tridentate N-ketopinidene-α-amino acids were synthesized. They serve as efficient catalysts for the enantioselective oxidative couplings of various 3-, 6-, or 7-substituted 2-naphthols. The best scenario involves the use of a vanadyl complex arising from L-tert-leucine in CCl4. The asymmetric couplings of 2-naphthols can be conducted smoothly at 40-45 °C under a stream of gaseous oxygen, leading to 2,2′dihydroxy-1,1′-binaphthyls in good yields (61-99%) and with enantioselectivities of up to 87%.