12-Bromododecanol
[CAS# 3344-77-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 12-Bromododecanol
• Synonyms: 12-Bromo-1-dodecanol
• Molecular Formula: C₁₂H₂₅BrO
• Molecular Weight: 265.23
• CAS Registry Number: 3344-77-2
• EC Number: 962-500-3
• SMILES: C(CCCCCCBr)CCCCCO

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Melting point: 34 - 36 ºC (Expl.)
• Boiling point: 299.5 ºC 760 mmHg (Calc.)^*, 362 ºC (Expl.)
• Flash point: 125.9±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: H302-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-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
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

12-Bromododecanol is an organic compound featuring a twelve-carbon linear alkyl chain with a hydroxyl group at one end (carbon 1) and a bromine atom at the opposite terminal carbon (carbon 12). Its molecular formula is C₁₂H₂₅BrO, classifying it as an ω-bromoalkanol. This bifunctional molecule contains both an alcohol and an alkyl halide functional group, making it a versatile intermediate in organic synthesis and materials science.

The synthesis of 12-bromododecanol is often performed by selective bromination of 1,12-dodecanediol, where one terminal hydroxyl group is converted to a bromide. Common brominating agents include phosphorus tribromide (PBr₃), hydrobromic acid (HBr), or other brominating reagents under controlled conditions to ensure selective substitution without affecting the other hydroxyl group. Alternative routes include nucleophilic substitution on terminal alkenes or via epoxide ring-opening reactions.

12-Bromododecanol's combination of hydroxyl and bromide functional groups allows for diverse chemical transformations. The hydroxyl group is reactive toward esterification, etherification, or oxidation, while the bromine atom acts as a good leaving group, making it susceptible to nucleophilic substitution reactions. These properties facilitate the introduction of various functional groups such as azides, amines, or thiols at the brominated terminus.

This compound is widely used as a building block in the synthesis of macrocycles, surfactants, polymers, and other functional materials. Intramolecular nucleophilic substitution can lead to the formation of twelve-membered ring ethers or amines, important structures in supramolecular chemistry and drug design. Additionally, its bifunctionality enables cross-linking or chain extension in polymer synthesis, impacting the mechanical and thermal properties of the resulting materials.

In surface chemistry and materials science, 12-bromododecanol is employed for functionalization of surfaces, nanoparticles, and polymers. The hydroxyl group can covalently attach to substrates, while the bromine terminus allows further chemical modification, enabling control over surface properties such as hydrophobicity, adhesion, and molecular arrangement.

Physically, 12-bromododecanol is typically a colorless to pale yellow liquid or low-melting solid at room temperature. It is sparingly soluble in water but dissolves readily in organic solvents including alcohols, ethers, and chlorinated solvents. The bromine substitution increases molecular weight and boiling point compared to non-halogenated analogs.

The compound requires careful handling due to its potential as an alkylating agent and irritant. It is sensitive to heat and light, which may promote decomposition or elimination reactions, so storage under inert atmosphere and away from moisture is recommended.

While 12-bromododecanol itself has limited direct pharmaceutical applications, derivatives synthesized from it are used in medicinal chemistry and biomaterials for linker design and molecular scaffolding. Its bifunctional nature facilitates conjugation reactions important in drug delivery and nanotechnology.

In summary, 12-bromododecanol is a versatile bifunctional intermediate widely used in organic synthesis, polymer chemistry, and materials science. Its reactive hydroxyl and bromide groups on a flexible alkyl chain provide chemical adaptability for diverse applications in industrial and academic fields.

References

2011. Synthesis of 15-(4-[11C]methylphenyl)pentadecanoic acid (MePPA) via Stille cross-coupling reaction. Journal of Radioanalytical and Nuclear Chemistry, 288(3).
DOI: 10.1007/s10967-011-1022-1

2016. SnCl4: An efficient and inexpensive promoter for synthesis of ω-functionalized alkyl 1,2-trans-glycosides from 1-O-pivaloyl donor. Russian Journal of General Chemistry, 86(1).
DOI: 10.1134/s1070363216010266

2001. Synthesis and Absolute Configuration of MQ-A3[1-(14'-Methylhexadecanoyl) pyrrolidine], a Novel Aliphatic Pyrrolidine Amide from the Tropical Convolvulaceous Species. Bioscience, Biotechnology, and Biochemistry, 65(2).
DOI: 10.1271/bbb.65.463