(R)-4-Benzyl-2-oxazolidinone
[CAS# 102029-44-7]

Identification

• Classification: Biochemical >> Peptide
• Name: (R)-4-Benzyl-2-oxazolidinone
• Synonyms: (4R)-4-benzyl-1,3-oxazolidin-2-one
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.20
• CAS Registry Number: 102029-44-7
• EC Number: 600-264-2
• SMILES: C1[C@H](NC(=O)O1)CC2=CC=CC=C2

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 88-90 °C (Expl.)
• alpha: 62 ° (C=1, CHCl3) (Expl.)
• Index of Refraction: 1.552, Calc.^*
• Boiling Point: 398.8±9.0 °C (760 mmHg), Calc.^*
• Flash Point: 195.0±18.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(R)-4-Benzyl-2-oxazolidinone is a chiral heterocyclic compound that has gained prominence in organic synthesis due to its utility as a chiral auxiliary and intermediate. Its structure consists of a five-membered oxazolidinone ring with a benzyl group at the 4-position, providing both stability and functionality in asymmetric synthesis.

The discovery of (R)-4-benzyl-2-oxazolidinone arose from the need for efficient chiral auxiliaries in the preparation of enantiomerically pure compounds. Early research on oxazolidinones highlighted their potential for inducing stereocontrol in reactions such as aldol condensations and Michael additions. The (R)-enantiomer, in particular, became a focus due to its superior ability to direct asymmetric transformations. Its synthesis is commonly achieved through the reaction of amino alcohols with benzyl halides, followed by cyclization with phosgene or phosgene substitutes.

One of the primary applications of (R)-4-benzyl-2-oxazolidinone is in the synthesis of chiral building blocks for pharmaceuticals and agrochemicals. By acting as a temporary chiral auxiliary, it facilitates the selective formation of one enantiomer over the other in complex molecules. The oxazolidinone ring provides rigidity, while the benzyl group enhances reactivity and stability in various chemical environments.

In the field of materials science, (R)-4-benzyl-2-oxazolidinone is explored as a precursor for the preparation of functionalized polymers and copolymers. Its ability to introduce chiral centers into polymer chains is valuable for developing advanced materials with specific optical and mechanical properties. These materials have potential applications in enantioselective catalysis, sensors, and drug delivery systems.

This compound is also studied in the development of sustainable chemical processes. Its efficient synthesis and recyclability make it a promising candidate for use in green chemistry. Researchers continue to investigate its role in reducing the environmental impact of asymmetric synthesis by minimizing waste and improving reaction efficiency.

While (R)-4-benzyl-2-oxazolidinone offers significant advantages, safe handling is essential due to its potential irritant properties. Careful adherence to safety guidelines ensures its effective use in both laboratory and industrial settings.

The compound remains an active area of research, with ongoing efforts to expand its applications and enhance its performance in various chemical and material contexts. Its contributions to the synthesis of enantiomerically pure compounds underscore its importance in advancing the fields of chemistry and materials science.

References

2018. Asymmetric Synthesis of Netarsudil: A New Therapeutic for Open-Angle Glaucoma. Synthesis, 51(06).
DOI: 10.1055/s-0037-1610310