299188-55-9

Basic information

• Product Name: (S)-2-HYDROXY-2-METHYL(2-NAPHTHALENE)ACETIC ACID
• Synonyms: (S)-2-HYDROXY-2-METHYL(2-NAPHTHALENE)ACETIC ACID;(2S)-2-(1,2-DIHYDRONAPHTHALEN-2-YL)-2-HYDROXYACETIC ACID
• CAS NO: 299188-55-9
• Molecular Formula: C13H12O3
• Molecular Weight: 216.23
• Mol File: 299188-55-9.mol

Chemical Properties

• Boiling Point: 419°C at 760 mmHg
• Flash Point: 221.3°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 9.08E-08mmHg at 25°C
• Refractive Index: 1.616
• PKA: 3.53±0.25(Predicted)
• CAS DataBase Reference: (S)-2-HYDROXY-2-METHYL(2-NAPHTHALENE)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-HYDROXY-2-METHYL(2-NAPHTHALENE)ACETIC ACID(299188-55-9)
• EPA Substance Registry System: (S)-2-HYDROXY-2-METHYL(2-NAPHTHALENE)ACETIC ACID(299188-55-9)

Safety Data

• Hazardous Substances Data: 299188-55-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H12O3/c13-11(12(14)15)10-6-5-8-3-1-2-4-9(8)7-10/h1-6,10-11,13H,7H2,(H,14,15)/t10?,11-/m0/s1

Upstream product

• 863922-58-1 (+/-)-methyl 2-hydroxy-2-(2-naphthyl)propionate 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 299188-57-1 (1R,2S,5R)-(-)-menthyl (S)-2-hydroxy-2-(2-naphthyl)propionate 
• 580-13-2 2-bromonaphthalene 
• 124-38-9 carbon dioxide 
• 93-08-3 methyl 2-naphthyl ketone 

Relevant articles and documents

Influence of magnesium(II) ions on cathodic reactions in aprotic solvents - Carboxylation of methyl aryl ketones

The presence in the medium of free MgII leads to a complete change in the voltammetry for the reduction of 2-acetylnaphthalene in DMF-Bu4NBF4 saturated with carbon dioxide. The mechanism for these changes has been investigated and it is confirmed that the Mg II interacts with the radical anions formed in the initial electron transfer reaction. The relevance of these conclusions to electrocarboxylations carried out in undivided cells with a sacrificial Mg anode is discussed. It is concluded that all the MgII formed at the anode is complexed strongly by the final carboxylated products from the cathode reaction and therefore the cathode reaction occurs in an environment where no free MgII ions are available. On the other hand, the complexation of the carboxylated products stabilises them to unwanted further reactions, thereby improving the selectivity of the electrosynthesis.

Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide

We have developed a new photocatalytic umpolung reaction of carbonyl compounds to generate anionic carbinol synthons. Aromatic aldehydes or ketones reacted with carbon dioxide in the presence of an iridium photocatalyst and 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole (DMBI) as a reductant under visible-light irradiation to furnish the corresponding α-hydroxycarboxylic acids through nucleophilic addition of the resulting carbinol anions to electrophilic carbon dioxide.

Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones

The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me2Zn and aminoalcohol catalyst promoted the aldol addition/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92 %), high enantioselectivities (up to 96 %), and complete diastereoselectivity. The chiral oxazolines were then used to give, after a straightforward acid hydrolysis, enantioenriched building blocks bearing tertiary alcohol motifs such as hydroxylaldehydes, hydroxylacids, and hydroxylesters without racemization.

On the enzymatic hydrolysis of methyl 2-fluoro-2-arylpropionates by lipases

The enzymatic hydrolysis of methyl 2-fluoro-2-arylpropionates was performed using lipases from Candida rugosa and Candida cylindracea (OF-360). A careful analysis of the reaction products revealed that racemic 2-hydroxy-2- arylpropionic acid and traces of 2-arylacrylic acid are formed, in addition to the expected 2-aryl-2-fluoropropionic acid. The presence of powerful electron-releasing groups in the aromatic ring of the substrate increase the amount of 2-hydroxypropionic acid. A mechanistic hypothesis has been formulated according to which the enzyme facilitates the elimination of fluoride ion from the hydrolysed acid with the formation of an α-carboxy-stabilized carbocation which provides 2-hydroxypropionic acids by nucleophilic attack of H2O and 2-arylacrylic acids by a β-elimination process.

Absolute configuration of 2-methoxy-2-(2-naphthyl)propionic acid as determined by the 1H NMR anisotropy method

2-Methoxy-2-(2-naphthyl)propionic acid 1 and 2-hydroxy-2-(2-naphthyl)propionic acid 2 were prepared by the Grignard reaction of 2-naphthylmagnesium bromide with (1R,2S,5R)-(-)-menthyl pyruvate. The absolute configurations of (+)-1 and (+)-2 were determined to be S by the 1H NMR anisotropy method. Copyright (C) 2000 Elsevier Science Ltd.

ELECTROCHEMICAL CARBOXYLATION OF ALDEHYDES AND KETONES WITH SACRIFICIAL ALUMINUM ANODES.

The electrocarboxylation of aldehydes to the corresponding α-hydroxyacids was described as impossible with conventional electrochemical systems.It is reported here that it is possible to realize it in diaphragmless cells making use of sacrificial aluminum anodes.The method can be used also for the electrocarboxylation of ketones with good yields.