144371-23-3

Basic information

• Product Name: (S)-2-(2-NAPHTHYL)GLYCOLIC ACID
• Synonyms: (S)-2-(2-NAPHTHYL)GLYCOLIC ACID;(S)-2-(2-NAPHTHYL)GLYCOLIC
• CAS NO: 144371-23-3
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• Mol File: 144371-23-3.mol

Chemical Properties

• Boiling Point: 428.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.354±0.06 g/cm3(Predicted)
• PKA: 3.42±0.30(Predicted)
• CAS DataBase Reference: (S)-2-(2-NAPHTHYL)GLYCOLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(2-NAPHTHYL)GLYCOLIC ACID(144371-23-3)
• EPA Substance Registry System: (S)-2-(2-NAPHTHYL)GLYCOLIC ACID(144371-23-3)

Safety Data

• Hazardous Substances Data: 144371-23-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-2-(2-NAPHTHYL)GLYCOLIC ACID is utilized as a key intermediate in the synthesis of various organic compounds. Its unique molecular structure, which includes a naphthalene moiety and a carboxylic acid group, allows for a wide range of chemical reactions and transformations, making it a versatile building block in the preparation of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-2-(2-NAPHTHYL)GLYCOLIC ACID is employed as a starting material for the development of novel drug candidates. Its chiral nature and the presence of a carboxylic acid group enable the formation of diverse chemical entities with potential therapeutic applications. Researchers can exploit its reactivity to design and synthesize new molecules with improved pharmacological properties, such as enhanced bioavailability, selectivity, and efficacy.
Used in Material Science:
(S)-2-(2-NAPHTHYL)GLYCOLIC ACID also finds applications in the field of material science, where it is used as a precursor for the synthesis of advanced materials with unique properties. Its incorporation into polymers, for instance, can lead to the development of new materials with improved mechanical strength, thermal stability, and other desirable characteristics. This makes it a valuable component in the creation of innovative materials for various industrial applications.
Used in Analytical Chemistry:
In analytical chemistry, (S)-2-(2-NAPHTHYL)GLYCOLIC ACID can be employed as a chiral reference compound or a derivatizing agent for the analysis of enantiomers. Its distinct stereochemistry allows for the differentiation between enantiomers in various analytical techniques, such as chromatography and spectroscopy. This makes it a useful tool in the study of chiral compounds and their properties, as well as in the development of enantioselective methods for the analysis of complex mixtures.

Upstream product

• 14289-44-2 (RS)-2-naphthylglycolic acid 
• 62-76-0 sodium oxalate 
• 66-99-9 β-naphthaldehyde 
• 20862-03-7 2-naphthyl cyanohydrin 
• 580-13-2 2-bromonaphthalene 
• 170166-53-7 methyl 2'-naphthoylformate 
• 14289-45-3 2-(naphthalen-2-yl)-2-oxoacetic acid 
• 93-08-3 methyl 2-naphthyl ketone 
• 91395-22-1 2,2-dichloro-1-(naphthalen-2-yl)ethan-1-one 

Relevant articles and documents

Oxalyl-CoA Decarboxylase Enables Nucleophilic One-Carbon Extension of Aldehydes to Chiral α-Hydroxy Acids

The synthesis of complex molecules from simple, renewable carbon units is the goal of a sustainable economy. Here we explored the biocatalytic potential of the thiamine-diphosphate-dependent (ThDP) oxalyl-CoA decarboxylase (OXC)/2-hydroxyacyl-CoA lyase (HACL) superfamily that naturally catalyzes the shortening of acyl-CoA thioester substrates through the release of the C1-unit formyl-CoA. We show that the OXC/HACL superfamily contains promiscuous members that can be reversed to perform nucleophilic C1-extensions of various aldehydes to yield the corresponding 2-hydroxyacyl-CoA thioesters. We improved the catalytic properties of Methylorubrum extorquens OXC by rational enzyme engineering and combined it with two newly described enzymes—a specific oxalyl-CoA synthetase and a 2-hydroxyacyl-CoA thioesterase. This enzymatic cascade enabled continuous conversion of oxalate and aromatic aldehydes into valuable (S)-α-hydroxy acids with enantiomeric excess up to 99 %.

The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation

A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX?Ru) catalyzed asymmetric hydrogenation of α-aryl keto acids has been successfully developed, affording the corresponding chiral α-aryl α-hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed to several chiral building blocks, biologically active compounds and chiral drugs. (Figure presented.).

Asymmetric hydrogenation reaction of alpha-ketoacids compound

The invention relates to the technical field of organic chemistry, especially to an asymmetric hydrogenation reaction of an alpha-ketoacids compound. The asymmetric hydrogenation reaction comprises a scheme shown in the description. In the scheme, R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, C1-C6 alkyl, or aralkyl; a substituent group is C1-C6 alkyl, C1-C6 alkoxy, or halogen; and the number of the substituent group is 1-3. In the scheme, M is a chiral spiro-pyridylamino phosphine ligand iridium complex having a structure shown in the description. In the structure, R is hydrogen, 3-methyl, 4-tBu, or 6-methyl.

Direct asymmetric hydrogenation of α-keto acids by using the highly efficient chiral spiro iridium catalysts

A new efficient and highly enantioselective direct asymmetric hydrogenation of α-keto acids employing the Ir/SpiroPAP catalyst under mild reaction conditions has been developed. This method might be feasible for the preparation of a series of chiral α-hydroxy acids on a large scale.

Hydrogen-bonding sheets in crystals for chirality recognition: synthesis and application of (2S,3S)-2,3-dihydroxy- and (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butanes

Two enantiopure bis(hydroxyamino) compounds were successfully prepared from dialkyl tartrate by a chiral-pool method and applied as basic resolving agents in the enantioseparation of 2-arylpropanoic acids and arylglycolic acids. (2S,3S)-2,3-Dihydroxy-1,4-bis(hydroxyamino)butane (2S,3S)-1a could moderately recognize the chirality of the 2-arylpropanoic acids, while (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butane (2S,3S)-1b could not due to the low crystallinity of both the corresponding diastereomeric salts. On the other hand, (2S,3S)-1b showed a similar chirality-recognition ability for the arylglycolic acids. The ability of (2S,3S)-1b was different from those generally observed for widely used primary amine-type resolving agents with regard to the relationship between the resolution efficiency and the similarity in the relative molecular length of a resolving agent and a target racemate. The X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that in the salts (2S,3S)-1a formed a supramolecular sheet, of which the distance was variable to make the resultant dissymmetric space fit to the shape of the target acids, and that (2S,3S)-1b was constructed from a robust supramolecular sheet, consisting of hydrogen-bonding 21 columns, with the participation of the hydroxy group of the arylglycolic acids. These X-ray crystallographic analyses also suggested that for the formation of a supramolecular sheet, the coexistence of two hydroxyamino groups is essential.

Process for preparing optically active amines and optically active carboxylic acids, and intermediates for preparation

Disclosed is a process for preparing an optically active 1-aryl- or 2-aryl-alkylamines of formulas Ia, Ib and Ic with high optical purity and high yield. The process uses an optically active 1- or 2-naphthylglycolic acid of the general formula II as a resolving agent. Also disclosed is a process for praparing an optically active 1- or 2-naphthylglycolic acid of formula II using an optically active 1-aryl- or 2-aryl-alkylamines of formulas Ia, Ib and Ic as the resolving agents

A high-performance, tailor-made resolving agent: Remarkable enhancement of resolution ability by introducing a naphthyl group into the fundamental skeleton1

A novel resolving agent, 2-naphthylglycolic acid (2-NGA), was designed for p-substituted 1-arylethylamines on the basis of the consideration that a rigid and large naphthyl group would be favorable for the close packing of supramolecular hydrogen-bond sheets formed between the carboxy groups of 2-NGA and the amino groups of p-substituted 1-arylethylamines. Racemic 2-NGA was readily available from commercially available raw materials, and both enantiopure forms could be obtained by simple diastereomeric resolution with enantiopure 1-phenyl-ethylamine. Thus-prepared enantiopure 2-NGA was found to have an excellent resolution ability not only for p-substituted 1-arylethylamines, but also for a wide variety of chiral primary amines. X-Ray crystallographic analyses of the less- and more-soluble diastereomeric salts revealed that this excellent resolution ability of 2-NGA arose from the formation of a supramolecular hydrogen-bond sheet with the primary amine, as we had expected, and also from the possible achievement of an infinite chain of CH... π interaction between its naphthyl group and the aromatic group of the amine, which was formed in the hydrophobic region of the supramolecular hydrogen-bond sheet.

(2-naphthyl)glycolic acid: A tailored resolving agent for p-substituted 1-arylethylamines

A tailored resolving agent for p-substituted l-arylethylamines, which was designed on the basis of a criterion derived from our crystal-structure study, namely that the racemate and the resolving agent should have similar molecular lengths, is described. The designed enantiopure (2- naphthyl)glycolie acid (2-NGA) showed excellent resolving ability for a wide variety of p-substituted l-arylethylamines.