1,10-Dibromodecane
[CAS# 4101-68-2]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1,10-Dibromodecane
• Molecular Formula: C₁₀H₂₀Br₂
• Molecular Weight: 300.08
• CAS Registry Number: 4101-68-2
• EC Number: 223-871-0
• SMILES: C(CCCCCBr)CCCCBr

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*, 1.335 g/mL (Expl.)
• Melting point: 25 - 27 °C (Expl.)
• Boiling point: 297.9±8.0 °C 760 mmHg (Calc.)^*, 317.7 °C (Expl.)
• Flash point: 153.4±17.7 °C (Calc.)^*, 112 °C (Expl.)
• Solubility: water: insoluble (Expl.)
• Index of refraction: 1.492 (Calc.)^*, 1.491 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety 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
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H302
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1,10-Dibromodecane is an organic compound characterized by a ten-carbon linear alkyl chain substituted with bromine atoms at both terminal carbons. Its molecular formula is C₁₀H₂₀Br₂, classifying it as a dihalogenated alkane, specifically an α,ω-dibromoalkane. The presence of two bromine atoms at the ends of the molecule imparts significant reactivity, making 1,10-dibromodecane a versatile intermediate in synthetic organic chemistry and materials science.

The synthesis of 1,10-dibromodecane is commonly achieved through the transformation of 1,10-decanediol by bromination. Typically, the terminal hydroxyl groups of the diol are replaced with bromine atoms using reagents such as phosphorus tribromide (PBr₃) or hydrobromic acid (HBr) under controlled conditions to ensure selective substitution and prevent side reactions. Alternative synthetic routes include the halogenation of terminal alkenes or nucleophilic substitution starting from other functionalized decane derivatives.

Due to its bifunctional bromine groups, 1,10-dibromodecane readily undergoes nucleophilic substitution reactions. This property facilitates the introduction of various nucleophiles such as amines, thiols, azides, or cyanides, enabling the synthesis of a wide range of functionalized molecules. Its bifunctionality makes it especially useful as a cross-linker, chain extender, or building block in the preparation of polymers, macrocycles, and other complex structures.

In macrocyclic chemistry, intramolecular nucleophilic substitution involving 1,10-dibromodecane can yield ten-membered ring compounds. These macrocycles find applications in supramolecular chemistry, molecular recognition, and as scaffolds in pharmaceutical and materials research.

In polymer science, 1,10-dibromodecane is used as a chain extender or cross-linking agent. Reaction with bifunctional nucleophiles such as diamines or dithiols produces polymers like polyamides and polythioethers, where the ten-carbon spacer imparts flexibility, hydrophobicity, and thermal stability to the polymer backbone. These properties influence the mechanical and physical behavior of the resulting materials.

Materials science applications include surface functionalization and nanostructure engineering. The bifunctional nature of 1,10-dibromodecane allows covalent bonding to various substrates, modifying surface properties such as adhesion, wettability, and molecular ordering. Such modifications are valuable in coatings, adhesives, and nanotechnology.

Physically, 1,10-dibromodecane is typically a colorless to pale yellow liquid or low-melting solid. It exhibits limited solubility in water but dissolves readily in organic solvents such as ethers, alcohols, and chlorinated hydrocarbons. The presence of bromine atoms increases its molecular weight, boiling point, and density relative to non-halogenated decanes.

Handling requires caution due to its alkylating potential and irritant properties. It is sensitive to light and heat, which can induce decomposition or elimination reactions, and thus should be stored in cool, dry, and dark conditions.

While 1,10-dibromodecane itself is not pharmacologically active, its derivatives are employed in medicinal chemistry for linker synthesis and molecular scaffold design. Its bifunctional bromide groups enable conjugation reactions important in drug delivery and biomaterials.

In summary, 1,10-dibromodecane is a versatile bifunctional intermediate widely used in organic synthesis, polymer chemistry, and materials engineering. Its reactive bromine termini and flexible alkyl chain facilitate diverse chemical transformations and applications across scientific and industrial domains.

References

2023. Synthesis of covalent organic pillars as molecular nanotubes with precise length, diameter and chirality. Nature Synthesis, 2(3).
DOI: 10.1038/s44160-022-00235-w

2021. Synthesis and crystalline structure of poly(p-phenylene alkylene)s and poly(p-phenylene co-alkylenes)s by Kumada coupling reaction of α,ω-dibromoalkane and p-dichlorobenzene. Journal of Polymer Research, 28(12).
DOI: 10.1007/s10965-021-02849-8

2019. The effect of the structure of a cross-linking reagent of the alkylating type on the properties of chitosan granules. Russian Chemical Bulletin, 68(6).
DOI: 10.1007/s11172-019-2551-y