550-97-0

Basic information

• Product Name: 2-Naphthol salicylate
• Synonyms: 2-Naphthol salicylate;Salicylic acid 1-naphtyl ester;1-Naphthyl Salicylate
• CAS NO: 550-97-0
• Molecular Formula: C₁₇H₁₂O₃
• Molecular Weight: 264.28
• Mol File: 550-97-0.mol

Chemical Properties

• Melting Point: 83°C
• Boiling Point: 367.51°C (rough estimate)
• Flash Point: 179.8°C
• Appearance: /
• Density: 1.1852 (rough estimate)
• Vapor Pressure: 9.27E-08mmHg at 25°C
• Refractive Index: 1.5490 (estimate)
• PKA: 7.88±0.30(Predicted)
• CAS DataBase Reference: 2-Naphthol salicylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthol salicylate(550-97-0)
• EPA Substance Registry System: 2-Naphthol salicylate(550-97-0)

Safety Data

• Hazardous Substances Data: 550-97-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H12O3/c18-15-10-4-3-9-14(15)17(19)20-16-11-5-7-12-6-1-2-8-13(12)16/h1-11,18H

Upstream product

• 90-15-3 α-naphthol 
• 69-72-7 salicylic acid 
• 444-30-4 2-(trifluoromethyl)phenol 
• 66691-27-8 2-(naphthalen-2-yloxy)-benzoic acid 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 613669-18-4 2-(naphthalen-1-yloxy)-benzoic acid 
• 118-55-8 phenyl Salicylate 

Downstream Products

• 155388-82-2 2-hydroxy-5-nitro-benzoic acid-[1]naphthyl ester 

Relevant articles and documents

Synthesis of salicylates from anionically activated aromatic trifluoromethyl group

An efficient approach to salicylates via a novel transformation of anionically activated aromatic trifluoromethyl group is described. Anionically activated trifluoromethyl group can react with phenols/alcohols under alkaline conditions to afford aryl/alkyl salicylates in high yields. Mechanism studies indicate that the carbonyl oxygen atom of ester is from the H2O in the solvent.

Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids

We report herein a cerium photocatalyzed aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement. This operationally simple protocol utilizes inexpensive CeCl3as a photocatalyst and converted a variety of 2-aryloxybenzoic acids into aryl-2-hydroxybenzoates in good yields.

A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids

We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.

Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement

We report herein, a silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C-O or C-S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.

Acylation of Phenols with Salicylic Acid Using Polyphosphoric Acid

Acylation of 2-naphthol (2), 1-naphthol (6) and resorcinol (11) with salicylic acid (1) in the presence of PPA affords salicylate esters (4, 7, 13 and 14), 1,2-benzoxanthone (5), 3,4-benzoxanthone (8), 3-hydroxyxanthone (12), 2-salicoyl-1-naphthol (9) and 11-hydroxy-12H-benzoxanthen-12-one (10).Compounds (4, 5, 7, 8, 12, 13 and 14) are identical with those obtained by heating a mixture of phenyl salicylate (3) and phenols (2, 6 and 11).

Thermal Conversion of Salol into Xanthone: A Mechanistic Study

The thermal conversion of salol (1) into xanthone has been rationalized as proceeding via the keto-ketene intermediate (7) which is trapped by phenols (9, 12 and 15).