25258-16-6

Basic information

• Product Name: (2S)-2-(naphthalen-2-yloxy)propanoic acid
• Synonyms: (2S)-2-(2-Naphthyloxy)propanoic acid; propanoic acid, 2-(2-naphthalenyloxy)-, (2S)-
• CAS NO: 25258-16-6
• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.2326
• Mol File: 25258-16-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 389.7°C at 760 mmHg
• Flash Point: 152.1°C
• Density: 1.231g/cm³
• Vapor Pressure: 9.05E-07mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: (2S)-2-(naphthalen-2-yloxy)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-(naphthalen-2-yloxy)propanoic acid(25258-16-6)
• EPA Substance Registry System: (2S)-2-(naphthalen-2-yloxy)propanoic acid(25258-16-6)

Safety Data

• Hazardous Substances Data: 25258-16-6(Hazardous Substances Data)

Upstream product

• 149880-48-8 (R)-2-(2-Naphthoxy)propionsaeure-ethylester 
• 135-19-3 β-naphthol 
• 10470-82-3 2-(2-naphthalenyloxy)propanoic acid 
• 62784-66-1 bis(1-naphthyl)methanol 
• 30406-75-8 2-(naphthalen-2-yloxy)-propionic acid methyl ester 
• 51-64-9 dexamfetamine 

Relevant articles and documents

A new method for production of chiral 2-aryloxypropanoic acids using effective kinetic resolution of racemic 2-aryloxycarboxylic acids

We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv2O) as an activating agent, bis(a-naphthyl)methanol ((α-Np)2CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.

Substitution of 2-(Sulfonyloxy)carboxylates with Oxygene and Sulfur Nucleophiles without Racemization

The ethyl 2-(sulfonyloxy)propionates (S)-1a-c react with phenolates formed from 2 and with carboxylates 8 to give the respective 2-(aryloxy)- (R)-3 and 2-(acyloxy)propionates (R)-9 with inversion of configuration.Due to the high leaving tendency of the triflate group, (S)-1a generally give higher yields of substitution products under milder conditions than the corresponding mesylate (S)-1b and tosylate (S)-1c.In the case of the reaction of malic and succinic acid derivatives only the triflate (S)-10a is converted to the acyloxy compounds (R)-12 with carboxylates 8 atlow temperature (-45 deg C); with the mesylates 10b and the bromide 10d only elimination is observed.Mercaptides and thiophenolates formed from 17 react with (S)-1a-c analogously.With potassium thiocyanate 1a,b react almost exclusively to give the thiocyanate 19; only traces of the corresponding isothiocyanate 20 are obtained.