Benzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetate
[CAS# 142504-42-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Benzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetate
• Molecular Formula: C₁₅H₂₂O₆
• Molecular Weight: 298.33
• CAS Registry Number: 142504-42-5
• EC Number: 810-282-4
• SMILES: C1=CC=C(C=C1)COC(=O)COCCOCCOCCO

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Benzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetate, also known by its chemical structure as a benzyl ester derivative of an ethoxy-substituted acetic acid, is an organic compound with a complex structure that includes both ether and ester functional groups. The molecule consists of a benzyl group attached to the acetic acid derivative, which features multiple ethoxy groups. These ethoxy groups play a significant role in the compound's solubility and reactivity, while the benzyl group adds to its potential for further chemical modifications.

The discovery of benzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetate is part of the broader field of research into multifunctional esters and ether derivatives, which are often synthesized for their unique chemical properties. Benzyl esters, in particular, are known for their versatility in organic synthesis, providing a stable and reactive functional group that can undergo hydrolysis, esterification, and nucleophilic substitution reactions. The presence of multiple ethoxy groups in the structure enhances the compound's solubility in polar solvents and makes it valuable in various chemical applications.

One of the primary applications of this compound is in the synthesis of pharmaceuticals and agrochemicals. The presence of the ester group makes it useful as an intermediate in the preparation of more complex organic molecules, while the ethoxy groups contribute to the compound's hydrophilic nature, improving its performance in certain formulations. In drug discovery, molecules with ether and ester linkages are often explored for their bioactivity, including their ability to interact with various biological targets.

Benzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetate is particularly valuable in the design and synthesis of prodrugs. Prodrugs are pharmacologically inactive compounds that undergo metabolic conversion in the body to release the active drug. The ester groups in this compound are prone to hydrolysis, which can release active pharmacophores upon administration. This property makes the compound useful in creating controlled-release formulations for drugs that require gradual activation in the body.

In addition to its applications in the pharmaceutical industry, this compound is also used in the synthesis of surfactants and emulsifiers. The presence of both hydrophobic (benzyl) and hydrophilic (ethoxy) groups in the structure allows the molecule to act as a bridge between different phases, making it effective in stabilizing emulsions and formulations. This makes it valuable in the production of personal care products, cleaning agents, and industrial formulations where surfactants are required to improve solubility, stability, and dispersion of active ingredients.

The compound's ability to function as a versatile building block is not limited to pharmaceuticals and surfactants. It is also used in polymer chemistry, where it serves as a precursor for the synthesis of polymers with specific solubility and mechanical properties. The modification of the benzyl ester group can lead to polymers that have applications in coatings, adhesives, and other materials that require specific solubility profiles.

Overall, benzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetate is an important compound in organic synthesis, offering a variety of applications in drug development, surfactant formulation, and materials science. Its ability to undergo various chemical reactions and its functional versatility make it a valuable intermediate in the creation of complex molecules for pharmaceutical and industrial use.

References

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