169557-36-2

Basic information

• Product Name: (S)-(+)-1,1''-BI-2-NAPHTHOL DIACETATE
• Synonyms: (S)-(+)-1,1'-BI-2-NAPHTHOL DIACETATE
• CAS NO: 169557-36-2
• Molecular Formula: C24H18O4
• Molecular Weight: 370.4
• Mol File: 169557-36-2.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-(+)-1,1''-BI-2-NAPHTHOL DIACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1,1''-BI-2-NAPHTHOL DIACETATE(169557-36-2)
• EPA Substance Registry System: (S)-(+)-1,1''-BI-2-NAPHTHOL DIACETATE(169557-36-2)

Safety Data

• Hazardous Substances Data: 169557-36-2(Hazardous Substances Data)

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 

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 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