(S)-(+)-Benzyl glycidyl ether
[CAS# 16495-13-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: (S)-(+)-Benzyl glycidyl ether
• Synonyms: (S)-(-)-2-(Benzyloxymethyl)oxirane
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20
• CAS Registry Number: 16495-13-9
• EC Number: 605-380-7
• SMILES: C1[C@H](O1)COCC2=CC=CC=C2

Properties

• Density: 1.072 g/mL (20 °C) (Expl.)
• Boiling point: 130 °C (0.1 mmHg) (Expl.)
• alpha: 5.1 ° (c=5 in toluene) (Expl.)
• Refraction index: 1.517 (Expl.)
• Flash point: 110 °C (Expl.)

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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(S)-(+)-Benzyl glycidyl ether is an organic compound that belongs to the class of glycidyl ethers, which are notable for their role in various chemical and industrial applications. This compound has a glycidyl ether structure, consisting of a benzyl group (C6H5CH2) attached to an epoxide group (a three-membered oxygen-containing ring). The (S)-(+)-configuration indicates that this compound is optically active, meaning it can rotate plane-polarized light in a specific direction, a property that is important for its reactivity and application in asymmetric synthesis. The chemical structure of (S)-(+)-benzyl glycidyl ether can be described as C9H10O2, with the oxygen atom bridging the two carbon atoms of the epoxide ring.

The discovery of (S)-(+)-benzyl glycidyl ether is part of the broader exploration of glycidyl ethers, which are widely studied due to their versatile reactivity and ability to undergo various chemical transformations. Glycidyl ethers like (S)-(+)-benzyl glycidyl ether are of particular interest because of their ability to participate in nucleophilic substitution reactions, making them valuable intermediates in organic synthesis. The (S)-enantiomer, in particular, is important in the development of chiral compounds, which are essential in the pharmaceutical industry and in the synthesis of fine chemicals.

One of the primary applications of (S)-(+)-benzyl glycidyl ether is in the field of asymmetric synthesis. The chiral nature of this compound allows it to be used as a building block for the creation of enantiomerically pure compounds. The ability to control the stereochemistry in reactions involving (S)-(+)-benzyl glycidyl ether is crucial in the production of various chiral molecules, which are essential for drug development and the production of specialty chemicals. This compound is used in the synthesis of chiral intermediates, which are often required in the preparation of pharmaceutical drugs, agrochemicals, and other biologically active molecules.

In addition to its role in asymmetric synthesis, (S)-(+)-benzyl glycidyl ether is also utilized in the production of epoxy resins. The epoxide group present in the molecule can undergo ring-opening reactions with various nucleophiles, such as amines, alcohols, and thiols, leading to the formation of crosslinked polymers. Epoxy resins, which are known for their strong adhesive properties, chemical resistance, and electrical insulating capabilities, are widely used in the coatings industry, electronics, and aerospace applications. The use of (S)-(+)-benzyl glycidyl ether in the formulation of epoxy resins helps enhance the properties of the final materials, such as their flexibility, thermal stability, and resistance to degradation.

(S)-(+)-benzyl glycidyl ether is also valuable in the synthesis of surfactants and other functional materials. Due to its ability to undergo nucleophilic substitution, it can be used to prepare functionalized surfactants, which are important in the formulation of detergents, emulsifiers, and dispersants. These surfactants are employed in a variety of industries, including personal care products, agriculture, and food processing. By modifying the structure of (S)-(+)-benzyl glycidyl ether, it is possible to design surfactants with specific properties, such as improved foaming characteristics, better wetting ability, or enhanced emulsifying power.

Another application of (S)-(+)-benzyl glycidyl ether is in the preparation of functional polymers. The epoxide group allows it to be incorporated into polymer chains, either as a monomer or as a functional group, to modify the properties of the polymer. These functionalized polymers can be used in a wide range of applications, including coatings, adhesives, and sealants. The ability to fine-tune the polymer properties by incorporating (S)-(+)-benzyl glycidyl ether makes it an important tool in materials science and engineering.

Furthermore, (S)-(+)-benzyl glycidyl ether has been explored for its potential use in drug delivery systems. The compound’s ability to form stable complexes with certain drugs or therapeutic agents opens avenues for targeted drug delivery. By attaching drugs to (S)-(+)-benzyl glycidyl ether, researchers are able to improve the solubility, stability, and bioavailability of drugs, as well as control the release rates, which is especially beneficial in the treatment of chronic diseases or conditions that require sustained drug release.

In conclusion, (S)-(+)-benzyl glycidyl ether is a versatile compound with a wide range of applications in the fields of asymmetric synthesis, polymer chemistry, surfactant production, and drug delivery. Its chiral nature and ability to undergo various chemical transformations make it an important intermediate for the synthesis of enantiomerically pure compounds, as well as a useful building block for the creation of functional materials. As research in the fields of organic chemistry and materials science continues to evolve, the importance of (S)-(+)-benzyl glycidyl ether is likely to grow, providing new opportunities for its use in both industrial and pharmaceutical applications.

References

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2008. A Straightforward Synthesis of Enantiopure 2,6-Disubstituted Morpholines by a Regioselective O-Protection/Activation Protocol. Synlett, 2008(16), 2455-2458.
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