Ethyl 10-bromodecanoate
[CAS# 55099-31-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 10-bromodecanoate
• Molecular Formula: C₁₂H₂₃BrO₂
• Molecular Weight: 279.21
• CAS Registry Number: 55099-31-5
• EC Number: 678-091-7
• SMILES: CCOC(=O)CCCCCCCCCBr

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.464, Calc.^*
• Boiling Point: 305.8±15.0 °C (760 mmHg), Calc.^*
• Flash Point: 160.3±10.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Ethyl 10-bromodecanoate is a versatile organic compound that plays a crucial role in synthetic chemistry, particularly as an intermediate for the production of diverse functional molecules. Its structure, consisting of a decanoate backbone with a bromine atom attached to the 10th carbon and an ethyl ester group, makes it highly reactive and suitable for various chemical transformations.

The synthesis of ethyl 10-bromodecanoate dates back to the exploration of brominated long-chain esters in organic synthesis. It is commonly prepared by brominating ethyl decanoate, a fatty acid ester, under controlled conditions using bromine or other brominating agents. Advances in synthesis have focused on improving yield, selectivity, and environmental sustainability, minimizing the production of byproducts.

Ethyl 10-bromodecanoate is widely used as a building block in pharmaceuticals, polymers, and specialty chemicals. Its bromine atom makes it highly reactive, enabling it to undergo substitution and coupling reactions, which are essential for creating more complex molecules. In pharmaceutical research, it is used to synthesize intermediates for drugs with antimicrobial, antifungal, or anticancer properties. The compound's long aliphatic chain contributes to lipophilicity, a critical factor in drug development.

In materials science, ethyl 10-bromodecanoate serves as a precursor in the manufacture of surfactants, lubricants, and polymers. For example, its transformation into alcohols, amines, or amides allows the design of molecules tailored for industrial applications, such as detergents and plasticizers. Additionally, it is utilized in radical polymerization processes to create high-performance materials.

Recent innovations have expanded the use of ethyl 10-bromodecanoate in green chemistry. Researchers have explored its potential in biodegradable polymer synthesis and environmentally friendly surfactant production, aiming to reduce ecological impact. Sustainable methods for its synthesis, such as using renewable feedstocks and minimizing halogenated waste, align with these goals.

The compound continues to be an indispensable tool for chemists, providing a foundation for the development of new materials and bioactive substances. Its versatility and reactivity ensure its relevance in diverse fields, from pharmaceuticals to advanced materials.

References

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