1,12-Dibromododecane
[CAS# 3344-70-5]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1,12-Dibromododecane
• Synonyms: Dodecamethylene dibromide
• Molecular Formula: C₁₂H₂₄Br₂
• Molecular Weight: 328.13
• CAS Registry Number: 3344-70-5
• EC Number: 222-096-5
• SMILES: C(CCCCCCBr)CCCCCBr

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Melting point: 38 - 42 °C (Expl.)
• Boiling point: 362.8 °C 760 mmHg (Calc.)^*, 390.8 °C (Expl.)
• Flash point: 180.2±18.2 °C (Calc.)^*, 113 °C (Expl.)
• Index of refraction: 1.49 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

1,12-Dibromododecane is an organic compound consisting of a twelve-carbon linear alkyl chain with bromine atoms attached at both terminal carbons. Its molecular formula is C₁₂H₂₄Br₂, classifying it as a dihalogenated alkane, specifically a α,ω-dibromoalkane. The presence of two bromine atoms at the termini confers significant chemical reactivity, making 1,12-dibromododecane a valuable intermediate in organic synthesis and materials science.

The typical synthesis of 1,12-dibromododecane involves the conversion of 1,12-dodecanediol into the corresponding dibromide. This transformation is usually achieved using brominating reagents such as phosphorus tribromide (PBr₃) or hydrobromic acid under carefully controlled conditions to selectively replace hydroxyl groups without causing side reactions. Alternative synthetic pathways include halogenation of terminal alkenes or nucleophilic substitution reactions starting from other functionalized dodecane derivatives.

Due to its bifunctional bromine groups, 1,12-dibromododecane readily undergoes nucleophilic substitution reactions, allowing the introduction of a wide range of functional groups such as amines, thiols, azides, or cyanides. This versatility enables its use as a difunctional alkylating agent in the preparation of macrocycles, polymers, and cross-linked materials.

In macrocyclic chemistry, intramolecular nucleophilic displacement of the bromine atoms can lead to the formation of twelve-membered ring compounds. Such macrocycles have applications in supramolecular chemistry, molecular recognition, and as building blocks in pharmaceutical research.

In polymer science, 1,12-dibromododecane serves as a chain extender or cross-linker. Reactions with bifunctional nucleophiles like diamines or dithiols can produce polyamides, polythioethers, and other polymers. The twelve-carbon alkyl spacer contributes flexibility, hydrophobicity, and thermal stability to the polymer backbones, affecting their mechanical and physical properties.

The compound is also employed in materials science for surface modification and functionalization. Its bifunctional nature allows covalent attachment to various substrates, influencing surface properties such as adhesion, wettability, and molecular organization. These properties are valuable in coatings, adhesives, and nanotechnology applications.

Physically, 1,12-dibromododecane is typically a colorless to pale yellow liquid or low-melting solid. It has limited solubility in water but dissolves readily in organic solvents including ethers, alcohols, and chlorinated hydrocarbons. The bromine atoms increase its molecular weight and polarizability, leading to higher boiling points and densities compared to non-halogenated alkanes of similar chain length.

Handling of 1,12-dibromododecane requires caution due to its potential alkylating activity and irritant effects. It is sensitive to heat and light, which can induce decomposition or elimination reactions, necessitating storage in a cool, dry place protected from light.

While 1,12-dibromododecane itself is not pharmacologically active, it serves as a versatile intermediate for synthesizing derivatives explored in medicinal chemistry and biomaterials development. Its bifunctional bromide groups facilitate the design of linkers and scaffolds useful in drug delivery and molecular engineering.

In summary, 1,12-dibromododecane is a valuable bifunctional intermediate widely applied in organic synthesis, polymer chemistry, and materials engineering. Its reactive bromine termini and flexible alkyl chain enable diverse chemical transformations and functionalities across multiple scientific and industrial fields.

References

2014. Features of the synthesis of isatins and isoindigo derivatives bearing long-chain haloalkyl substituents. Monatshefte für Chemie - Chemical Monthly, 145(12).
DOI: 10.1007/s00706-014-1356-9

2013. 1-((12-Bromododecyl)oxy)-4-((4-(4-pentylcyclohexyl)phenyl)ethynyl) benzene: Liquid crystal with aggregation-induced emission characteristics. Science China Chemistry, 56(12).
DOI: 10.1007/s11426-013-4950-5

2015. Three gemini cationic surfactants as biodegradable corrosion inhibitors for carbon steel in HCl solution. Research on Chemical Intermediates, 41(12).
DOI: 10.1007/s11164-015-2076-4