1,13-Dibromotridecane
[CAS# 31772-05-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Alkane
• Name: 1,13-Dibromotridecane
• Molecular Formula: C₁₃H₂₆Br₂
• Molecular Weight: 342.15
• CAS Registry Number: 31772-05-1
• SMILES: C(CCCCCCBr)CCCCCCBr

Properties

• Density: 1.3 g/cm³ Calc.^*
• Boiling point: 350.0 ºC 760 mmHg (Calc.)^*
• Flash point: 192.7 ºC (Calc.)^*
• Index of refraction: 1.489 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Danger
• Hazard Statements: H302-H315-H318-H410
• Precautionary Statements: P280-P301+P312+P330-P305+P351+P338+P310
• Transport Information: UN 3082

Discovory and Applicatios

1,13-Dibromotridecane is an organic compound featuring a linear thirteen-carbon alkyl chain substituted with bromine atoms at both terminal positions. Its molecular formula is C₁₃H₂₆Br₂, classifying it as a dihalogenated alkane, specifically a dibromo derivative of tridecane. The presence of two bromine atoms at opposite ends of the molecule imparts significant reactivity, making it a valuable intermediate in synthetic organic chemistry and materials science.

The compound is commonly synthesized via the halogenation of 1,13-tridecanediol or through the dibromination of terminal alkenes possessing a thirteen-carbon backbone. One established synthetic route involves the conversion of terminal hydroxyl groups in 1,13-tridecanediol to bromides using reagents such as phosphorus tribromide (PBr₃) or hydrobromic acid under controlled reaction conditions to avoid side reactions. Alternatively, bromine addition across terminal double bonds followed by subsequent chain manipulations can yield 1,13-dibromotridecane.

1,13-Dibromotridecane’s two electrophilic bromine termini make it highly reactive toward nucleophilic substitution, facilitating the introduction of various functional groups such as amines, thiols, azides, or cyanides. This reactivity allows the compound to serve as a bifunctional alkylating agent in the synthesis of macrocycles, polymers, and cross-linked materials.

One notable application is in the formation of macrocyclic compounds via intramolecular nucleophilic substitution, where the terminal bromides can be displaced to close the carbon chain into rings of varying sizes. These macrocycles are of interest in supramolecular chemistry, host–guest systems, and as scaffolds for drug development.

In polymer chemistry, 1,13-dibromotridecane is utilized as a chain extender or cross-linker. Reaction with nucleophilic monomers such as diamines or dithiols can yield polyamides, polythioethers, or other functional polymers with tailored mechanical and thermal properties. The thirteen-carbon spacer contributes to flexibility and hydrophobic character within polymer backbones.

In materials science, the compound is employed for surface functionalization and nanostructure modification. Its bifunctionality allows for covalent attachment to diverse substrates, enabling control over surface properties like hydrophobicity, adhesion, and molecular spacing in coatings, adhesives, and nanomaterials.

Physically, 1,13-dibromotridecane is typically a colorless to pale yellow liquid or low-melting solid with limited solubility in water but good solubility in organic solvents such as ethers, alcohols, and chlorinated hydrocarbons. The presence of bromine increases molecular weight, density, and boiling point compared to non-halogenated analogs.

The compound must be handled with care due to its alkylating potential and possible irritant effects. It is sensitive to light and heat, which may induce elimination or decomposition reactions, requiring storage under inert atmosphere and protection from moisture.

Although 1,13-dibromotridecane itself is not pharmacologically active, its derivatives are explored in medicinal chemistry for linker design and molecular scaffolding. Its bifunctional nature facilitates conjugation reactions important in drug delivery and biomaterials.

Overall, 1,13-dibromotridecane is a versatile bifunctional intermediate widely used in organic synthesis, polymer science, and materials engineering. Its reactive bromine termini and long alkyl chain enable diverse chemical transformations and functional applications across multiple scientific and industrial domains.

References

1989. Liquid crystalline polyethers based on conformational isomerism. Polymer Bulletin, 22(5-6).
DOI: 10.1007/bf00718924