53408-43-8

Basic information

• Product Name: methyl 2-(2,3-dihydroxypropoxy)benzoate
• CAS NO: 53408-43-8
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.2259
• Mol File: 53408-43-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 409.6°C at 760 mmHg
• Flash Point: 160.2°C
• Density: 1.258g/cm³
• Vapor Pressure: 1.92E-07mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: methyl 2-(2,3-dihydroxypropoxy)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(2,3-dihydroxypropoxy)benzoate(53408-43-8)
• EPA Substance Registry System: methyl 2-(2,3-dihydroxypropoxy)benzoate(53408-43-8)

Safety Data

• Hazardous Substances Data: 53408-43-8(Hazardous Substances Data)

Upstream product

• 69-72-7 salicylic acid 
• 119-36-8 methyl salicylate 
• 6282-42-4 methyl 2-allyloxybenzoate 
• 556-52-5 oxiranyl-methanol 

Relevant articles and documents

A Structure-Reactivity Relationship of the Tandem Asymmetric Dihydroxylation on a Biologically Relevant Diene: Influence of Remote Stereocenters on Diastereofacial Selectivity

The Sharpless asymmetric dihydroxylation (AD) finds widespread use in natural product and drug molecule syntheses, in part, due to its efficiency and predictability. However, the tandem AD of dienes is much less studied, but important in complex molecular synthesis. Herein, a biologically relevant tandem AD is reported, and several anomalies are discovered with the accepted model. These include the formation of unpredicted diastereoisomers, with matched and mismatched stereocenters contradicting the Sharpless mnemonic device. From a structural analysis of the tandem AD, we present a strategy to improve asymmetric induction in sterically hindered alkenes using double diastereodifferentiation from a 9-bond distant stereocenter. A theoretical justification for the unpredicted stereoselectivity, accounting for the influence of steric hindrance and pre-installed chirality, is proposed.