Ethyl butylacetylaminopropionate
[CAS# 52304-36-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphonate / phosphonate
• Name: Ethyl butylacetylaminopropionate
• Synonyms: Ethyl N-acetyl-N-butyl-beta-alaninate
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.29
• Protein Sequence: X
• CAS Registry Number: 52304-36-6
• EC Number: 257-835-0
• SMILES: CCCCN(CCC(=O)OCC)C(=O)C

Properties

• Density: 1.0$+/-$0.1 g/cm³ Calc.^*
• Boiling point: 314.8$+/-$25.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 144.2$+/-$23.2 $degree$C (Calc.)^*
• Index of refraction: 1.45 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Ethyl butylacetylaminopropionate is an ester derivative of an amino acid-like structure, in which a propionate backbone is substituted with an acetylated amino group and esterified with an ethyl moiety. The molecule combines ester functionality with an acylated amino group, providing both lipophilic and reactive characteristics. This structural arrangement allows the compound to act as an intermediate in the synthesis of biologically active molecules and specialized chemical products.

The molecular structure consists of a three-carbon propionate chain with a nitrogen atom bonded to an acetyl group, forming an amide linkage. The terminal carboxyl group of the propionate is esterified with an ethyl group, producing the ethyl ester. The butyl group attached to the nitrogen increases hydrophobicity, which can influence solubility, partitioning behavior, and reactivity in chemical or biological systems. The combination of ester and amide functionalities provides sites for hydrolysis, acylation, or substitution reactions, making it versatile in synthetic chemistry.

Synthesis of ethyl butylacetylaminopropionate typically involves the acylation of the corresponding amino propionate with butylacetyl chloride or an equivalent acylating agent, followed by esterification of the carboxylic acid with ethanol. Reaction conditions are controlled to avoid over-acylation or side reactions, ensuring high-purity product suitable for further applications. The ester and amide groups are stable under standard storage conditions, facilitating handling and use in downstream processes.

One major application of this compound is as an intermediate in the preparation of pharmaceuticals, bioactive molecules, or fragrance compounds. Its structural features, including the lipophilic butyl group and polar amide linkage, allow it to serve as a building block for molecules designed to interact with biological systems or chemical formulations where controlled solubility and reactivity are required. It can also be modified through hydrolysis or further acylation to produce derivatives with specific properties.

In addition, ethyl butylacetylaminopropionate is used in chemical synthesis as a versatile reagent for constructing more complex molecules. The reactive amide and ester functionalities allow for participation in condensation reactions, nucleophilic substitutions, and hydrolytic transformations. This versatility makes it suitable for research in organic chemistry and industrial applications where functionalized propionate derivatives are needed.

Overall, ethyl butylacetylaminopropionate is a multifunctional ester-amide compound with important utility in organic synthesis, pharmaceutical intermediate chemistry, and functional molecule development. Its combination of ester, amide, and lipophilic substituents provides both reactivity and solubility versatility, making it a valuable building block for complex chemical and biologically active compounds.

References

2025. Investigating the role of mosquito repellents in atopic dermatitis. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
DOI: 10.1016/j.fct.2025.115571

2024. Study of sorption properties of zirconia, alumina, and silica in relation to repellents. Colloid and Polymer Science.
DOI: 10.1007/s00396-024-05260-z

2022. 3D-printing of the polymer/insect-repellent system poly(l-lactic acid)/ethyl butylacetylaminopropionate (PLLA/IR3535). International Journal of Pharmaceutics.
DOI: 10.1016/j.ijpharm.2022.122023