11-Bromo-1-undecanol
[CAS# 1611-56-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 11-Bromo-1-undecanol
• Synonyms: Undecamethylene bromohydrin
• Molecular Formula: C₁₁H₂₃BrO
• Molecular Weight: 251.21
• CAS Registry Number: 1611-56-9
• EC Number: 216-554-3
• SMILES: C(CCCCCO)CCCCCBr

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Melting point: 46 - 49 ºC (Expl.)
• Boiling point: 349.6 ºC 760 mmHg (Calc.)^*, 430.3 - 438 ºC (Expl.)
• Flash point: 122.4±10.1 ºC (Calc.)^*, 113 ºC (Expl.)
• Index of refraction: 1.476 (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.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

11-Bromo-1-undecanol is an organic compound characterized by an eleven-carbon linear alkyl chain bearing a hydroxyl group at the first carbon and a bromine atom at the terminal (eleventh) carbon. Its molecular formula is C₁₁H₂₃BrO, classifying it as an ω-bromoalkanol. This bifunctional molecule combines both alcohol and alkyl halide functionalities, rendering it a valuable intermediate in synthetic organic chemistry and materials science.

The synthesis of 11-bromo-1-undecanol typically involves selective functionalization of 1,11-undecanediol. One common approach is the substitution of the terminal hydroxyl group at carbon 11 by bromine using reagents such as phosphorus tribromide (PBr₃), hydrobromic acid, or other brominating agents under controlled conditions to avoid multiple substitutions or degradation. Alternatively, the compound can be prepared by nucleophilic ring-opening of an epoxide intermediate bearing the appropriate carbon chain length.

The dual functionality of 11-bromo-1-undecanol offers versatile reactivity. The primary alcohol group at carbon 1 is reactive toward esterification, etherification, or oxidation, whereas the bromine substituent at carbon 11 is a good leaving group, making it susceptible to nucleophilic substitution reactions. This allows for a wide range of chemical modifications, including the introduction of azide, thiol, amine, or other nucleophilic groups at the terminal position. Such transformations facilitate the synthesis of complex molecules and functionalized materials.

One of the primary applications of 11-bromo-1-undecanol lies in the synthesis of macrocyclic compounds and heterocycles. Intramolecular nucleophilic substitution reactions can induce cyclization to form eleven-membered ring ethers (oxacycloundecanes) or amines, depending on the nucleophile employed. These macrocycles are of interest in host–guest chemistry, supramolecular assemblies, and as building blocks in pharmaceuticals and material science.

In polymer and surface chemistry, 11-bromo-1-undecanol serves as a precursor for modifying polymer end groups or functionalizing surfaces. Its long alkyl chain imparts hydrophobic character, while the reactive termini enable covalent attachment to polymers, nanoparticles, or surfaces through ester, ether, or amide linkages. It is employed in preparing surfactants, lubricants, and coatings where tailored surface properties such as wettability and adhesion are desired.

From a physical standpoint, 11-bromo-1-undecanol is a colorless to pale yellow liquid or low-melting solid under ambient conditions. It exhibits low solubility in water but dissolves readily in organic solvents such as alcohols, ethers, and chlorinated hydrocarbons. Its boiling point and density are elevated relative to non-halogenated alcohols due to the presence of the bromine atom.

The stability of 11-bromo-1-undecanol requires storage under inert conditions to prevent decomposition or elimination reactions, especially when exposed to light or heat. The bromine substituent can act as an alkylating agent and should be handled with appropriate safety precautions.

Although 11-bromo-1-undecanol itself does not have direct pharmacological applications, derivatives synthesized from it are explored in medicinal chemistry for drug design and delivery. Its role as a bifunctional linker facilitates conjugation of bioactive molecules or polymers, contributing to controlled drug release or targeting.

Overall, 11-bromo-1-undecanol is a well-documented bifunctional intermediate in organic synthesis, material science, and polymer chemistry. Its combination of reactive alcohol and bromide groups on a flexible alkyl chain enables diverse chemical transformations and functional applications across various scientific and industrial fields.

References

2017. Selective Aerobic Oxidation of Primary Alcohols to Aldehydes. Synlett, 28(4).
DOI: 10.1055/s-0036-1588155

2012. Synthesis of fluorescent long-chain thiols/disulfides as building-blocks for self-assembled monolayers preparation. Central European Journal of Chemistry, 10(2).
DOI: 10.2478/s11532-011-0140-5

2006. A site-directed spin-labeling study of surfactants in polymer–clay nanocomposites. Colloid and Polymer Science, 284(10).
DOI: 10.1007/s00396-006-1499-2