87-16-1

Basic information

• Product Name: 2-methoxyphenyl salicylate
• Synonyms: 2-methoxyphenyl salicylate;Guaiacol salol;Salicylic acid 2-methoxyphenyl ester
• CAS NO: 87-16-1
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24268
• EINECS: 201-726-2
• Mol File: 87-16-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 400.3°C at 760 mmHg
• Flash Point: 152.5°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 5.54E-07mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: 2-methoxyphenyl salicylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxyphenyl salicylate(87-16-1)
• EPA Substance Registry System: 2-methoxyphenyl salicylate(87-16-1)

Safety Data

• Hazardous Substances Data: 87-16-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12O4/c1-17-12-8-4-5-9-13(12)18-14(16)10-6-2-3-7-11(10)15/h2-9,15H,1H3

Upstream product

• 90-05-1 2-methoxy-phenol 
• 69-72-7 salicylic acid 
• 79365-16-5 2-(2'-methoxyphenoxy)benzonitrile 
• 444-30-4 2-(trifluoromethyl)phenol 
• 21905-73-7 2-carboxy-2'-methoxydiphenyl ether 

Downstream Products

• 55482-89-8 Guaiaspir 
• 1245937-10-3 C₁₇H₁₆O₄ 

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.

Preparation method for guacetisal

The invention discloses a preparation method for guacetisal. The preparation method comprises the following steps: with salicylic acid as a starting material, activating salicylic acid with N,N'-carbonyldiimidazole; then reacting activated salicylic acid with guaiacol so as to obtain guaiacol salicylate; and carrying out hydroxyacetylation so as to obtain guacetisal. The preparation method provided by the invention has the following advantages: the preparation method is formulated via improvement of conventional synthetic routes; the preparation method avoids usage of reagents with great toxicity and strong irritation, such as phosphorous oxychloride, thionyl chloride and phosgene; reaction temperature is substantially lowered; reaction conditions are mild; and the method is simple to operate. It is unexpectedly discovered in the invention that a novel crystal form of guacetisal is prepared by using the preparation method; and compared with conventional crystal forms, the novel crystal form improves the water-solubility and stability of guacetisal, allows the contents of related substances to be substantially reduced, and greatly improved medication security.

Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis

We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature. Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C?O bond cleavage, we developed a novel approach to the C?O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a one-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.