10-Bromodecanol
[CAS# 53463-68-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 10-Bromodecanol
• Synonyms: 10-Bromo-1-decanol
• Molecular Formula: C₁₀H₂₁BrO
• Molecular Weight: 237.18
• CAS Registry Number: 53463-68-6
• EC Number: 258-572-4
• SMILES: C(CCCCCBr)CCCCO

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*, 1.19 g/mL (Expl.)
• Boiling point: 288.6±13.0 °C 760 mmHg (Calc.)^*, 340.4 - 345.8 °C (Expl.)
• Flash point: 118.3±9.5 °C (Calc.)^*
• Index of refraction: 1.476 (Calc.)^*, 1.476 (Expl.)

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

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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

10-Bromodecanol is an organic compound consisting of a ten-carbon linear alkyl chain bearing a hydroxyl group at one end (carbon 1) and a bromine atom at the opposite end (carbon 10). Its molecular formula is C₁₀H₂₁BrO. This bifunctional molecule belongs to the class of ω-bromoalkanols and features both alcohol and alkyl bromide functional groups, which confer significant chemical versatility and reactivity.

The synthesis of 10-bromodecanol is commonly achieved by selective bromination of 1,10-decanediol, where one terminal hydroxyl group is converted to a bromide while the other remains intact. Brominating reagents such as phosphorus tribromide (PBr₃) or hydrobromic acid (HBr) are typically employed under controlled reaction conditions to ensure selective monobromination. Alternative synthetic pathways include nucleophilic substitution of corresponding tosylate or mesylate derivatives or ring-opening reactions of epoxides.

10-Bromodecanol’s bifunctionality allows for diverse chemical modifications. The hydroxyl group is reactive toward esterification, etherification, and oxidation, whereas the bromine atom acts as a good leaving group in nucleophilic substitution reactions. This dual reactivity enables the introduction of a variety of nucleophiles such as amines, thiols, azides, or cyanides at the brominated terminus.

This compound is widely utilized as an intermediate in the synthesis of macrocycles, polymers, surfactants, and other functional materials. Intramolecular nucleophilic substitution involving the bromine and hydroxyl groups can lead to the formation of ten-membered ring ethers or amines, which have significance in supramolecular chemistry and medicinal chemistry. Additionally, 10-bromodecanol can serve as a cross-linker or chain extender in polymer chemistry, influencing the mechanical and thermal properties of the resulting polymers.

In materials science, 10-bromodecanol is employed for surface functionalization of nanoparticles, polymers, and substrates. The hydroxyl group facilitates covalent attachment to surfaces, while the bromine terminus allows further chemical modification, enabling control over surface properties such as adhesion, hydrophobicity, and molecular ordering.

Physically, 10-bromodecanol is typically a colorless to pale yellow liquid or low-melting solid. It is sparingly soluble in water but dissolves well in organic solvents including ethers, alcohols, and chlorinated hydrocarbons. The presence of bromine increases the molecular weight, boiling point, and density relative to non-halogenated decanols.

Handling 10-bromodecanol requires caution due to its potential alkylating properties and irritant effects. It is sensitive to light and heat, which can promote decomposition or elimination reactions. Therefore, it should be stored in cool, dry, and dark conditions to maintain stability.

While 10-bromodecanol itself has limited direct pharmaceutical activity, its derivatives are explored in drug design, biomaterials, and nanotechnology. Its bifunctional structure facilitates conjugation reactions important in drug delivery systems and molecular engineering.

In summary, 10-bromodecanol is a versatile bifunctional intermediate with hydroxyl and bromide groups at opposite ends of a ten-carbon chain. Its chemical reactivity and structural features enable diverse applications in organic synthesis, polymer chemistry, and materials science.

References

2022. Like Visiting an Old Friend: Fischer Glycosylation in the Twenty-First Century: Modern Methods and Techniques. Topics in current chemistry (Cham), 380(4).
DOI: 10.1007/s41061-022-00383-9

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 (11Z,13Z)-11,13-Hexadecadienal, the Female Sex Pheromone of the Navel Orangeworm. Bioscience, Biotechnology, and Biochemistry, 73(12).
DOI: 10.1271/bbb.90611