8-Bromo-1-octanol
[CAS# 50816-19-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 8-Bromo-1-octanol
• Molecular Formula: C₈H₁₇BrO
• Molecular Weight: 209.12
• CAS Registry Number: 50816-19-8
• EC Number: 256-785-7
• SMILES: C(CCCCBr)CCCO

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*, 1.22 g/mL (Expl.)
• Boiling point: 282.1 °C 760 mmHg (Calc.)^*, 379.7 - 381.5 °C (Expl.)
• Flash point: 105.2±12.3 °C (Calc.)^*, 110 °C (Expl.)
• Index of refraction: 1.477 (Calc.)^*, 1.48 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

8-Bromo-1-octanol is an organic compound featuring an eight-carbon linear alkyl chain with a hydroxyl group at the first carbon and a bromine atom at the eighth carbon. Its molecular formula is C₈H₁₇BrO. As an ω-bromoalkanol, it contains both an alcohol and a bromide functional group on opposite ends of the molecule, which imparts bifunctionality and makes it a versatile intermediate in organic synthesis and materials chemistry.

The synthesis of 8-bromo-1-octanol is typically performed by selective bromination of 1,8-octanediol, converting one terminal hydroxyl group into a bromide. This transformation is commonly achieved using reagents such as phosphorus tribromide (PBr₃), hydrobromic acid (HBr), or other brominating agents under controlled conditions to ensure substitution at only one terminus. Alternative synthetic routes include nucleophilic substitution of corresponding tosylates or mesylates or via ring-opening of epoxides.

The bifunctional nature of 8-bromo-1-octanol, possessing both a reactive hydroxyl and bromide group, enables diverse chemical transformations. The hydroxyl group can undergo esterification, etherification, or oxidation, while the bromine atom acts as a good leaving group, making the molecule susceptible to nucleophilic substitution. This allows for the introduction of various functional groups such as amines, thiols, azides, or cyanides at the brominated terminus.

8-Bromo-1-octanol is widely utilized as a building block in the synthesis of macrocycles, surfactants, polymers, and other functional materials. Intramolecular nucleophilic substitution can lead to the formation of eight-membered ring ethers or amines, which are significant in supramolecular chemistry and medicinal chemistry. Additionally, its bifunctionality enables cross-linking or chain extension in polymer synthesis, impacting mechanical and thermal properties.

In materials science, 8-bromo-1-octanol is employed for surface functionalization of nanoparticles, polymers, and other substrates. The hydroxyl group facilitates covalent attachment to surfaces, while the bromine terminus provides sites for further chemical modification, enabling fine control over surface characteristics such as hydrophobicity, adhesion, and molecular organization.

Physically, 8-bromo-1-octanol is typically a colorless to pale yellow liquid or low-melting solid. It has limited solubility in water but dissolves well in organic solvents such as ethers, alcohols, and chlorinated hydrocarbons. The bromine substitution increases molecular weight and boiling point compared to non-halogenated octanols.

Handling requires caution due to its potential alkylating activity and irritant effects. It is sensitive to heat and light, which may promote decomposition or elimination reactions, thus it should be stored in a cool, dry, and dark environment.

Although 8-bromo-1-octanol itself has limited direct pharmaceutical applications, derivatives synthesized from it are explored in drug design and biomaterials science. Its bifunctional structure facilitates conjugation reactions important in drug delivery and nanotechnology.

In summary, 8-bromo-1-octanol is a versatile bifunctional intermediate featuring a hydroxyl and bromide group on an eight-carbon chain. Its chemical reactivity and structural features enable diverse applications in organic synthesis, polymer chemistry, and materials science.

References

2021. Continuous synthesis of bromoalkyl glycosides by Fischer glycosylation in a microreactor. Journal of Flow Chemistry, 11(3).
DOI: 10.1007/s41981-021-00202-0

2009. New synthesis of nematocidal natural products dithiocynates thiocyanatin A and 1,8,16-trihydroxyhexadecane. Natural Product Research, 23(10).
DOI: 10.1080/14786410802587073

1982. New synthesis of royal jelly acid. Journal of Chemical Ecology, 8(4).
DOI: 10.1007/bf00988312