291772-40-2

Basic information

• Product Name: (R)-1,1'-BI-2-NAPHTHOL DIBENZOATE
• Synonyms: (R)-1,1'-BI-2-NAPHTHOL DIBENZOATE;(S)-1,1'-BI-2-NAPHTHOL DIBENZOATE;(R)-1,1'-Bi-2-naphthol dibenzoate,98%;[1,1'-Binaphthalene]-2,2'-diol,dibenzoate, (1S)- (9CI)
• CAS NO: 291772-40-2
• Molecular Formula: C34H22O4
• Molecular Weight: 494.54
• Mol File: 291772-40-2.mol

Chemical Properties

• Melting Point: 163-166 °C
• Boiling Point: 729.2°Cat760mmHg
• Flash Point: 380.6°C
• Appearance: /
• Density: 1.268g/cm³
• CAS DataBase Reference: (R)-1,1'-BI-2-NAPHTHOL DIBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1,1'-BI-2-NAPHTHOL DIBENZOATE(291772-40-2)
• EPA Substance Registry System: (R)-1,1'-BI-2-NAPHTHOL DIBENZOATE(291772-40-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 291772-40-2(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Upstream product

• 98-88-4 benzoyl chloride 
• 602-09-5 1,1'-bi-2-naphthol 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 

Relevant articles and documents

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols

An operationally simple isothiourea-catalysed acylative kinetic resolution of unprotected 1,1′-biaryl-2,2′-diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high s values; ii) the use of an α,α-disubstituted mixed anhydride (2,2-diphenylacetic pivalic anhydride) was critical to minimize diacylation and give high selectivity; iii) the presence of substituents in the 3,3′-positions of the diol hindered effective acylation. This final observation was exploited for the highly regioselective acylative kinetic resolution of unsymmetrical biaryl diol substrates bearing a single 3-substituent. Based on the key observations identified, acylation transition state models have been proposed to explain the atropselectivity of this kinetic resolution.

Catalyst components for the polymerization of olefins

A solid catalyst component for the polymerization of olefins comprising Mg, Ti, Cl and at least an electron donor compound which is the reaction product obtained by bringing into contact a Mg compound and a Ti compound having at least a Ti-halogen bond with an electron donor selected from specific diphenol derivatives.

Efficient routes to racemic and enantiomerically pure (s)-binol diesters

A systematic study for esterification procedures to the synthesis of BINOL diesters is described. Reaction conditions with trifluoracetic acid anhydride (TFAA) and 85% H3PO4 were selected as the best procedure to prepare enantiomeric

Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)3

Bi(OTf)3-catalyzed acylation of alcohols with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)3/acid anhydride protocol was so powerful that sterically demanding or tertiary alcohols could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technology was developed in order to overcome difficulty in separation of the acylated product from the remaining acylating reagent: methanolysis of the unreacted anhydride into easily separable methyl ester realized quite easy separation of the desired acylation product. The Bi(OTf)3/acid anhydride protocol was applicable to a wide spectrum of alcohols bearing various functionalities. Acid-labile THP- or TBS-protected alcohol, furfuryl alcohol, and geraniol could be acylated as well as base-labile alcohols. Even acylation of functionalized tertiary alcohols was effected at room temperature.