Prop-2-en-1-yl 4-aminobenzoate
[CAS# 62507-78-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Prop-2-en-1-yl 4-aminobenzoate
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.20
• CAS Registry Number: 62507-78-2
• SMILES: C=CCOC(=O)C1=CC=C(C=C1)N

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

Prop-2-en-1-yl 4-aminobenzoate is an ester compound in which the carboxyl group of 4-aminobenzoic acid is esterified with an allyl alcohol (prop-2-en-1-ol). The molecule combines an aromatic amine functional group with an allyl ester moiety, providing both nucleophilic and electrophilic reactivity. This structural arrangement allows it to serve as a versatile intermediate in organic synthesis, particularly for the preparation of substituted amides, carbamates, and other functionalized derivatives.

The synthesis of prop-2-en-1-yl 4-aminobenzoate typically involves esterification of 4-aminobenzoic acid with allyl alcohol under acidic or catalytic conditions. Common methods include the use of acid catalysts or carbodiimide-mediated coupling to promote ester formation while preserving the amino group. Careful control of temperature and stoichiometry is required to avoid side reactions such as over-acylation or polymerization. The product is usually isolated through crystallization or chromatographic purification to yield a solid or viscous liquid suitable for further transformations.

In synthetic chemistry, prop-2-en-1-yl 4-aminobenzoate is used as an intermediate for constructing various amide, carbamate, or ester derivatives. The allyl ester provides a reactive handle for subsequent transformations, including palladium-catalyzed cross-coupling, Claisen rearrangement, or selective hydrolysis. The aromatic amino group can be acylated, alkylated, or converted into diazonium salts, enabling diverse functionalization and incorporation into more complex molecules.

In medicinal chemistry, derivatives of this compound are explored for potential bioactivity. The aromatic amine can engage in hydrogen bonding and receptor interactions, while the ester functionality allows modification of lipophilicity, solubility, and metabolic stability. The allyl group can serve as a precursor for further functionalization to tune pharmacokinetic properties, facilitating the design of small-molecule drug candidates or prodrugs.

The compound is also relevant in materials science and polymer chemistry. The allyl ester can undergo polymerization or participate in cross-linking reactions, allowing incorporation into polymer backbones or surface coatings. The combination of aromatic and allylic functionalities makes it suitable for preparing functionalized monomers, resins, or photoactive materials.

Physically, prop-2-en-1-yl 4-aminobenzoate is typically obtained as a solid or viscous liquid with moderate solubility in polar organic solvents such as ethanol, dichloromethane, and dimethylformamide. It is generally stable under ambient conditions but should be protected from strong acids, bases, and oxidizing agents that could hydrolyze the ester or modify the amino group. Proper storage ensures its utility in synthetic, medicinal, and material applications.

Overall, prop-2-en-1-yl 4-aminobenzoate is a multifunctional ester combining an allyl moiety with an aromatic amine. Its dual reactivity and structural versatility make it a valuable intermediate for organic synthesis, functionalization, drug design, and polymer applications.

References

2011. Poly(dimethylsiloxane-urethane) membranes: effect of linear siloxane chain and caged silsesquioxane on gas transport properties. Journal of Polymer Research, 18(6).
DOI: 10.1007/s10965-011-9592-8