617-01-6

Basic information

• Product Name: o-tolyl salicylate
• Synonyms: o-Tolyl salicylate; 2-Methylphenyl 2-hydroxybenzoate; 2-Methylphenyl salicylate; AI3-19490; Benzoic acid, 2-hydroxy-, 2-methylphenyl ester; Cresyl salicylate, o-; FEMA No. 3734; Salicylic acid, o-tolyl ester; Tolyl salicylate, o-
• CAS NO: 617-01-6
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.2433
• EINECS: 210-500-2
• Mol File: 617-01-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 379.3°C at 760 mmHg
• Flash Point: 162.5°C
• Density: 1.216g/cm³
• Vapor Pressure: 2.72E-06mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: o-tolyl salicylate(CAS DataBase Reference)
• NIST Chemistry Reference: o-tolyl salicylate(617-01-6)
• EPA Substance Registry System: o-tolyl salicylate(617-01-6)

Safety Data

• Hazardous Substances Data: 617-01-6(Hazardous Substances Data)

Usage

General Description

o-Tolyl salicylate, also known as 2-hydroxybenzoic acid o-tolyl ester, is a chemical compound with the molecular formula C14H12O3. It is commonly used in the production of sunscreens and cosmetic products due to its UV-absorbing properties. o-Tolyl salicylate works by absorbing and dissipating UV radiation, thereby protecting the skin from sun damage and premature aging. It is a white crystalline solid that is insoluble in water but soluble in organic solvents. As a chemical ingredient in sunscreens, o-Tolyl salicylate plays a critical role in protecting the skin from harmful UV rays and reducing the risk of skin cancer and other sun-related skin conditions.

Upstream product

• 444-30-4 2-(trifluoromethyl)phenol 
• 95-48-7 ortho-cresol 
• 67698-66-2 2-(2-methylphenoxy)benzaldehyde 
• 21905-71-5 1-methyl-2-(2-methylphenoxy)benzoate 
• 6325-68-4 2-(2-methylphenoxy)benzoic acid 
• 69-72-7 salicylic acid 

Downstream Products

• 107410-04-8 2,4'-dihydroxy-3'-methyl-benzophenone 
• 88599-47-7 2-Carbamoyloxy-benzoic acid o-tolyl ester 
• 128916-11-0 2-Allyloxy-benzoic acid o-tolyl 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.

N-Heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement: Synthesis of aryl salicylates from: O -aryl salicylaldehydes

The N-heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement of O-aryl salicylaldehydes was developed. Both electron-deficient and electron-rich aryls worked well as migrating groups, giving the corresponding aryl salicylates in good yields. This reaction features formation of two new C-O bonds and one C-O bond cleavage via metal-free oxidation of the Breslow intermediate using oxygen as the terminal oxidant and following the Smiles rearrangement under photocatalysis.

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.