100569-82-2

Basic information

• Product Name: DL-1,1'-BI(2-NAPHTHYL DIACETATE)
• Synonyms: (+/-)-2,2'-DIACETOXY-1,1'-BINAPHTHYL;2,2'-DIACETOXY-1,1'-BINAPHTHYL;DL-1,1'-BI(2-NAPHTHYL DIACETATE);(R)-(-)-2,2'-DIACETOXY-1,1'-BINAPHTHYL;(R)-(-)-1,1'-BI-2-NAPHTHOL DIACETATE;(S)-(+)-2,2'-DIACETOXY-1,1'-BINAPHTHYL;1,1'-BI-2-NAPHTHYL DITACETATE;(+)-1,1'-Bi-2-NaphtholDiAcetate
• CAS NO: 100569-82-2
• Molecular Formula: C₂₄H₁₈O₄
• Molecular Weight: 370.4
• Mol File: 100569-82-2.mol

Chemical Properties

• Melting Point: 107-111 °C(lit.)
• Boiling Point: 460.3°C (rough estimate)
• Flash Point: 270.8°C
• Appearance: /
• Density: 1.1610 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• CAS DataBase Reference: DL-1,1'-BI(2-NAPHTHYL DIACETATE)(CAS DataBase Reference)
• NIST Chemistry Reference: DL-1,1'-BI(2-NAPHTHYL DIACETATE)(100569-82-2)
• EPA Substance Registry System: DL-1,1'-BI(2-NAPHTHYL DIACETATE)(100569-82-2)

Safety Data

• Hazard Codes: Xi
• Statements: 41-37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 100569-82-2(Hazardous Substances Data)

Usage

Chemical Properties

white to beige powder

Upstream product

• 75-36-5 acetyl chloride 
• 602-09-5 1,1'-bi-2-naphthol 
• 108-24-7 acetic anhydride 
• 135-19-3 β-naphthol 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 100569-82-2 2,2'-diacetoxy-1,1'-binaphthyl 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 79044-27-2 (±)-1-(2-hydroxynapthalen-1-yl)napthalen-2-yl acetate 

Downstream Products

• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 79044-27-2 (±)-1-(2-hydroxynapthalen-1-yl)napthalen-2-yl acetate 
• 69677-98-1 (R)-[1,1′-binaphthalene]-2,2′-diyl diacetate 
• 169557-36-2 1,1'-bi(2-naphthyl) diacetate 

Relevant articles and documents

Rapid Synthesis of Alkenylated BINOL Derivatives via Rh(III)-Catalyzed C-H Bond Activation

Modification of BINOL units has been well examined via Rh-catalyzed C-H activation and functionalization reactions by using ester carbonyls as directing groups and alkenes as coupling partners. The one-pot strategy was an efficient protocol for the rapid synthesis of BINOL derivatives with retention of optical purity.

Rational design of BINOL-based diimidazolyl ligands: Homochiral channel-like mono-component organic frameworks by hydrogen-bond-directed self-assembly

We have developed a synthetic strategy to selectively incorporate the imidazole ring into the 1,1′-bi-2-naphthol (BINOL) skeleton at the different position. The resulting conformationally rigid BINOL-based diimidazolyl ligands bearing both hydrogen-bond-acceptors and -donators can self-assemble into homochiral channel-like mono-component organic frameworks via intermolecular O-H...N hydrogen bonds between the phenolic hydroxyl group and the N2 or N4 atom of the imidazole ring.

Continuous Flow Preparation of Enantiomerically Pure BINOL(s) by Acylative Kinetic Resolution

A polystyrene-immobilized isothiourea has been applied to the enantioselective acylative kinetic resolution (KR) of monoacylated BINOL(s) with inexpensive isobutyric anhydride in batch and flow. High selectivity values (s=29 at 0 °C) and a remarkable stability of the catalytic system in the operation conditions have been recorded for unsubstituted BINOL. No significant loss of activity/selectivity is recorded after 10 consecutive KR cycles in batch. A continuous flow process has been implemented and operated with a 100 mmol (32.8 g) sample of racemic monoacetylated BINOL in dichloromethane solution in an 84 hours experiment with a packed bed reactor containing 1 g (f=0.37 mmol.g?1) of the functional resin (s=17–21). Residence time can be decreased to 10 min with the same reactor to achieve a conversion of 58% with a selectivity factor s=17 when a more highly functionalized catalyst (f=0.88 mmol.g?1) is used. This translates into a remarkable combined productivity of 5.5 mmolprod ? mmolcat?1 ? h?1.

Arthrobacter sp. lipase catalyzed kinetic resolution of BINOL: The effect of substrate immobilization

(S)-1,1′-Binaphthyl-2,2′-diol was prepared in high optical purity (～98%) via Arthrobacter sp. lipase (MTCC No. 5125) catalyzed kinetic resolution. The immobilization of the substrate on a solid inert support significantly improved the enantioselectivity factor (E) by almost sixfolds, i.e. from ～27 to >180. The effect of acyl substituents and co-solvents were also studied.

N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) as an efficient catalyst for acetylation of alcohols, phenols, amines, and thiols under solvent-free conditions

N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) (NIBTS) is a highly efficient catalyst for the acetylation of alcohols, phenols, amines, and thiols under solvent-free conditions. Primary, secondary, tertiary alcohols; phenols; amines; and thiols can be easily acetylated in good to excellent yields at 80 C. Copyright Taylor & Francis Group, LLC.

Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols

Herein we report a dramatic acceleration of the lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols by the addition of sodium carbonate. This result likely originates from the increased nucleophilicity of the phenolic hydroxyl group toward the acyl-enzyme intermediate. Under these conditions, various substituted C2-symmetric and non-C2-symmetric binaphthols and biphenols were efficiently resolved with ～50% conversion in only 13-30 h with excellent enantioselectivity.

Efficient acetylation of alcohols and phenols catalyzed by recyclable lithium bis(perfluoroalkylsulfonyl)imide

An efficient acetylation of alcohols and phenols catalyzed by lithium bis(perfluoroalkylsulfonyl)-imide was developed. This acetylation features good yields, mild reaction condtions, and simple workup procedures. Furthermore, the catalyst bearing a long perfluoroalkyl chain is recoverable and readily reusable without losing any activity. Copyright

Convenient method for the synthesis of 6,6′-diacyl-1,1′-bi-2- naphthyl ethers

Acylation of 1,1′-bi-2-naphthol (BINOL) ethers using Lewis acids aluminum(III) chloride and titanium(IV) chloride gave the corresponding 6,6′-diacyl derivatives in good yields. Georg Thieme Verlag Stuttgart.

Ultrasonic speed and related acoustical parameters of 1,1'-Binaphthalene-2, 2'-diyl diacetate solutions at 308.15 K

The density (ρ), viscosity (η) and ultrasonic speed (U) (2MHz) of chloroform, THF, ethyl alcohol, ethyl acetate, 1,4-dioxane and 1,1'-binaphthalene-2,2'-diyl diacetate (DBNA) solutions have been determined at 308.15 K. Various acoustical parameters namely specific acoustical impedance (Z), adiabatic compressibility (ka), Van der Waals constant (b), intermolecular path length (Lf), internal pressure (π), Rao's molar sound function (R), relaxation time (τ), classical absorption coefficient (α/f2)cl and solvation number (Sn) have been derived from ρ, η and U data and correlated with concentration (C). A fairly good to excellent correlation has been observed between a particular parameter and C. Linear increase of Z, R, b, (α/f2) Cl and τ (except EA) (R2 = 0.90 - 0.999) and linear decrease of ks, π and Lf (R2 = 0.947 - 0.995) with C supported existence of powerful molecular interactions in the solutions and further supported by nonlinear increase of Sn with C. A fairly constant Gibbs free energy of activation has been observed in all the solvent systems studied.

Zeolite HSZ-360 as a new reusable catalyst for the direct acetylation of alcohols and phenols under solventless conditions

Alcohols and phenols were efficiently acylated with acetic anhydride without solvent over zeolite HSZ-360. The catalyst can be reused with no activity loss.