69677-98-1

Basic information

• Product Name: (S)-(+)-1,1'-Bi(2-naphthyl diacetate)
• Synonyms: (R)-(-)-2,2'-DIACETOXY-1,1'-BINAPHTHYL;(R)-(-)-1,1'-BI-2-NAPHTHOL DIACETATE;(S)-(+)-2,2'-DIACETOXY-1,1'-BINAPHTHYL;(S)-(+)-1,1'-BI(2-NAPHTHYL DIACETATE);DL-1,1'-BI(2-NAPHTHYL DIACETATE);(+/-)-2,2'-DIACETOXY-1,1'-BINAPHTHYL;2,2'-DIACETOXY-1,1'-BINAPHTHYL;(S)-(+)-1,1'-Bi(2-naphthyl diacetate),98%
• CAS NO: 69677-98-1
• Molecular Formula: C₂₄H₁₈O₄
• Molecular Weight: 374.43
• Product Categories: API intermediates
• Mol File: 69677-98-1.mol
• Article Data: 23

Chemical Properties

• Melting Point: 107-111 °C(lit.)
• Boiling Point: 532.2 °C at 760 mmHg
• Flash Point: 270.8 °C
• Appearance: white crystalline powder
• Density: 1.242 g/cm³
• Water Solubility: Insoluble
• CAS DataBase Reference: (S)-(+)-1,1'-Bi(2-naphthyl diacetate)(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1,1'-Bi(2-naphthyl diacetate)(69677-98-1)
• EPA Substance Registry System: (S)-(+)-1,1'-Bi(2-naphthyl diacetate)(69677-98-1)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 69677-98-1(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Upstream product

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

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

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.

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