111058-32-3

Basic information

• Product Name: (R)-Methyglycidate
• Synonyms: (2r)-oxirane-2-carboxylic acid methyl ester;methyl (2r)-oxirane-2-carboxylate;(r)-methyglycidate;METHYL (2R)-GLYCIDATE 97% (94% EE/GLC);methyl (r)-oxiranecarboxylate;R-METHYL OXIRANECARBOXYLATE;(R)-Methyl oxirane-2-carboxylate;(R)-Methyclycidate
• CAS NO: 111058-32-3
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09
• EINECS: 1592732-453-0
• Mol File: 111058-32-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 97.45 °C at 760 mmHg
• Flash Point: 162 °F
• Appearance: Clear colorless or slightly yellow liquid
• Density: 1.166 g/mL at 25 °C(lit.)
• Vapor Pressure: 41.693mmHg at 25°C
• Refractive Index: n20/D 1.42(lit.)
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Chloroform (Soluble), Ethyl Acetate (Slightly)
• Stability: Volatile
• CAS DataBase Reference: (R)-Methyglycidate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Methyglycidate(111058-32-3)
• EPA Substance Registry System: (R)-Methyglycidate(111058-32-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 111058-32-3(Hazardous Substances Data)

Usage

Description

(R)-Methyglycidate, also known as (R)-Methoxyacetaldehyde, is an organic compound with the chemical formula C3H6O2. It is a white solid that exhibits unique chemical properties, making it a versatile building block in the synthesis of various pharmaceuticals and other organic compounds.

Uses

Used in Pharmaceutical Industry:
(R)-Methyglycidate is used as a key intermediate in the synthesis of antibacterial oxazolidinones. These oxazolidinones are a class of antibiotics that are effective against a wide range of gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). The unique structure of (R)-Methyglycidate allows for the development of new and potent antibacterial agents to combat drug-resistant infections.
In addition to its use in the pharmaceutical industry, (R)-Methyglycidate can also be utilized in other applications, such as:
Used in Chemical Synthesis:
(R)-Methyglycidate is used as a versatile building block in the synthesis of various organic compounds. Its reactivity and functional groups make it suitable for use in the preparation of a wide range of chemical products, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Research and Development:
(R)-Methyglycidate serves as an important compound in research and development efforts, particularly in the field of organic chemistry. Its unique properties and reactivity make it a valuable tool for studying reaction mechanisms, developing new synthetic methods, and exploring the potential applications of novel compounds.

InChI:InChI=1/C4H6O3/c1-6-4(5)3-2-7-3/h3H,2H2,1H3/t3-/m1/s1

Upstream product

• 4538-50-5 methyl glycidate 
• 473-81-4 D-glyceric acid 
• 77-78-1 dimethyl sulfate 
• 56-45-1 L-serin 
• 82044-23-3 R-oxiranecarboxylic acid potassium salt 
• 82079-45-6 potassium de l'acide (S)-(-)-epoxy-2,3 propionique 

Downstream Products

• 124980-98-9 (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate 
• 114990-90-8 glycidic acid 
• 82079-45-6 potassium de l'acide (S)-(-)-epoxy-2,3 propionique 
• 54814-41-4 3-(3,4-dimethoxy-phenyl)-2-hydroxy-propionic acid methyl ester 

Relevant articles and documents

Synthesis of the fungal macrolide berkeleylactone A and its inhibition of microbial biofilm formation

The fungal macrolide berkeleylactone A was synthesised in 13 steps and 24% yield using (R)-propylene oxide and an asymmetric Noyori hydrogenation of a β-ketoester to install the stereogenic centres. A domino addition-Wittig olefination of a 13-hydroxytetradecanal intermediate with the cumulated ylide Ph3PCCO closed the macrocyle by establishing the α,β-unsaturated ester group, necessary for the attachment of the sidechain thiol via a thia-Michael reaction. The synthetic berkeleylactone A inhibited the formation of Staphylococcus aureus biofilms and showed significant dispersive effects on preformed biofilms of Candida albicans by at least 45% relative to untreated controls at concentrations as low as 1.3 μg mL-1.

Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides

Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.

A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions

The (salen)Co catalyst (4a) can be prepared as a mixture of cyclic oligomers in a short, chromatography-free synthesis from inexpensive, commercially available precursors. This catalyst displays remarkable enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen)Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of water and carbamates; and the desymmetrization of oxetanes by intramolecular ring opening with alcohols and phenols. The favorable solubility properties of complex 4a under the catalytic conditions facilitated mechanistic studies, allowing elucidation of the basis for the beneficial effect of oligomerization. Finally, a catalyst selection guide is provided to delineate the specific advantages of oligomeric catalyst 4a relative to (salen)Co monomer 1 for each reaction class.