9-Bromo-1-nonanol
[CAS# 55362-80-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: 9-Bromo-1-nonanol
• Molecular Formula: C₉H₁₉BrO
• Molecular Weight: 223.15
• CAS Registry Number: 55362-80-6
• EC Number: 611-262-6
• SMILES: C(CCCCO)CCCCBr

Properties

• Melting point: 33-35 °C
• Boiling point: 125-126 °C (2 mmHg)
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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

Discovery and Applications

9-Bromo-1-nonanol is a chemical compound with notable applications in synthetic organic chemistry. It is categorized as a brominated alcohol, where a bromine atom is attached to the nonanol backbone, a nine-carbon chain with an alcohol group at the terminal position. This compound is primarily utilized in chemical synthesis and material science due to its versatile reactivity and functional properties.

The discovery of 9-bromo-1-nonanol can be traced back to research on brominated alcohols, which are important intermediates in organic synthesis. The compound is produced through the bromination of 1-nonanol, a non-branching alcohol with nine carbon atoms. The process typically involves the reaction of 1-nonanol with bromine or brominating agents under controlled conditions to introduce the bromine atom at the 9th position of the carbon chain.

One of the significant applications of 9-bromo-1-nonanol is in the synthesis of more complex organic molecules. The presence of the bromine atom in the molecule makes it a valuable intermediate for further chemical transformations. For instance, 9-bromo-1-nonanol can undergo various substitution reactions to introduce different functional groups, making it useful in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

In material science, 9-bromo-1-nonanol has been used in the development of functionalized polymers and materials. The bromine atom in the compound serves as a reactive site for polymerization and cross-linking reactions, allowing for the creation of polymers with specific properties and functionalities. This application is particularly relevant in the field of polymer chemistry, where precise control over the polymer structure is essential.

The compound also finds use in the preparation of liquid crystals and other electronic materials. The long carbon chain of 9-bromo-1-nonanol, combined with its bromine functionality, can influence the alignment and properties of liquid crystal phases. This makes it a valuable component in the development of advanced display technologies and other electronic applications.

Additionally, 9-bromo-1-nonanol has potential applications in medicinal chemistry. The ability to introduce and modify functional groups through bromination provides a pathway for the development of novel bioactive compounds. Researchers have explored its use as an intermediate in the synthesis of various pharmaceuticals, where the bromine atom can be strategically utilized to enhance biological activity or selectivity.

In summary, 9-bromo-1-nonanol is a versatile chemical compound with significant applications in organic synthesis, material science, and medicinal chemistry. Its discovery has enabled advancements in the development of complex organic molecules, functionalized polymers, and electronic materials. The ability to use 9-bromo-1-nonanol as an intermediate highlights its importance in various fields of chemical research and industry.

References

2018. Redox-responsive ferrocene-containing poly(ionic liquid)s for antibacterial applications. Science China Chemistry.
DOI: 10.1007/s11426-018-9348-5

2005. A Synthetic Approach to Sporotricale Methylether. Synlett.
DOI: 10.1055/s-2005-917096