Ethyl 8-bromooctanoate
[CAS# 29823-21-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 8-bromooctanoate
• Molecular Formula: C₁₀H₁₉BrO₂
• Molecular Weight: 251.16
• CAS Registry Number: 29823-21-0
• EC Number: 608-417-5
• SMILES: CCOC(=O)CCCCCCCBr

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.463, Calc.^*
• Boiling Point: 267.1±23.0 ºC (760 mmHg), Calc.^*, 120-123 ºC (3 mmHg) (Expl.)
• Flash Point: 139.5±13.0 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary 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
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Ethyl 8-bromooctanoate is an organic compound belonging to the family of esters, commonly synthesized by the reaction of 8-bromooctanoic acid with ethanol. Its molecular structure consists of an octanoate group, which is a saturated fatty acid chain, bonded to an ethyl ester. The discovery of ethyl 8-bromooctanoate can be traced back to the continued development of ester compounds in the 20th century, which were used extensively in the synthesis of fragrances, pharmaceuticals, and other organic materials. As a specialized chemical, ethyl 8-bromooctanoate gained attention due to its unique chemical properties and applications.

In terms of its chemical properties, ethyl 8-bromooctanoate is a clear liquid at room temperature and exhibits moderate solubility in water and high solubility in organic solvents. It has a distinctive ester-like odor and is widely utilized as a building block in chemical synthesis due to its reactivity. The bromine atom in the compound serves as an important electrophilic site, making it useful in a range of organic reactions, such as nucleophilic substitution reactions and Suzuki coupling, which are valuable in the preparation of other complex organic compounds.

One of the primary applications of ethyl 8-bromooctanoate is in the field of organic synthesis, where it is employed as an intermediate in the production of more complex chemicals. It is particularly useful in the creation of molecules with biologically active properties, such as those needed in the pharmaceutical and agrochemical industries. For example, ethyl 8-bromooctanoate has been used as a precursor in the synthesis of molecules for pest control, with research indicating that brominated fatty acid esters can exhibit antimicrobial and antifungal properties.

In the fragrance industry, ethyl 8-bromooctanoate is used for its ability to modify the scent profile of other compounds, contributing to the production of novel scents. Its long alkyl chain imparts a waxy or floral odor, which can be used in the development of fragrances with longer-lasting properties. Additionally, the compound is also a subject of study in the development of new materials, including those used for drug delivery systems, where its ester functional group can be useful for modifying the solubility and bioavailability of active pharmaceutical ingredients.

The synthetic applications of ethyl 8-bromooctanoate are not limited to the pharmaceutical and fragrance industries. Researchers continue to explore its utility in materials science, particularly in the development of surfactants, polymers, and biodegradable plastics. The versatility of ethyl 8-bromooctanoate, alongside its relatively straightforward synthesis, makes it a valuable tool for developing new materials with varied applications.

In summary, ethyl 8-bromooctanoate is an important ester compound with a range of applications in organic synthesis, the fragrance industry, and material science. Its discovery and continued use reflect the versatility of ester compounds in developing novel chemical products, from pharmaceuticals to materials with unique properties.