11-Bromo-1-undecene
[CAS# 7766-50-9]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 11-Bromo-1-undecene
• Synonyms: 1-Bromo-10-undecene; 10-Undecenyl bromide; NSC 139878
• Molecular Formula: C₁₁H₂₁Br
• Molecular Weight: 233.19
• CAS Registry Number: 7766-50-9
• EC Number: 622-571-0
• SMILES: C=CCCCCCCCCCBr

Properties

• Solubility: Insoluble (1.4E^-3 g/L) (25 °C), Calc.^*
• Density: 1.083 g/cm³ (20 °C)^**
• Melting point: 55 °C^***
• Boiling point: 136-141 °C (15 Torr)^****
• Refractive index: 1.47 (589.3 nm 21 °C)^*****
• Flash point: 110.3±6.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

^** Sorensen, Jorgine S.

^*** Maisch, Steffen

^**** Diaper, D. G. M.

^***** Nair, M. S. R.

Safety Data

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

Discovery and Applications

11-Bromo-1-undecene is an organic compound belonging to the class of alkenes. It is a member of the brominated alkene family, characterized by a bromo group attached to the 11th carbon atom of an undecene chain. This compound is commonly used in organic synthesis and is valued for its versatility in the production of various chemical products. 11-Bromo-1-undecene is primarily used in the preparation of polymers, specialty chemicals, and in research applications that involve the functionalization of organic molecules. The compound's development was part of a broader effort to create halogenated alkenes with specific reactivity profiles that could be used in polymerization and other synthetic processes.

The synthesis of 11-bromo-1-undecene typically involves the halogenation of undecene using bromine or a bromine-containing reagent. The reaction proceeds through an electrophilic addition mechanism, where the bromine atom attaches to the carbon-carbon double bond of undecene. The presence of the bromine atom makes the compound reactive, allowing it to undergo further reactions, such as nucleophilic substitution or polymerization. This reactivity is key to its use in various chemical transformations, including the preparation of more complex molecules.

In terms of applications, 11-bromo-1-undecene is widely utilized in the synthesis of functionalized polymers. The bromo group on the 11th carbon atom serves as an electrophilic site for further chemical modifications. This feature is particularly useful in the synthesis of block copolymers, where the bromine atom can react with other functional groups to form a variety of polymer architectures. Additionally, the compound is employed in the creation of surfactants, which are used in detergents and other cleaning products. Its unique chemical structure also allows it to be used as a precursor for more complex organic compounds, including those used in pharmaceutical and agricultural chemistry.

In research, 11-bromo-1-undecene is used as a reagent in the development of new synthetic methodologies. Its ability to undergo various reactions makes it an ideal building block in the preparation of other functionalized alkenes and heterocycles. Furthermore, it is studied for its potential applications in materials science, particularly in the creation of functionalized coatings and surface treatments. The compound's utility in these areas is enhanced by its ease of synthesis and the wide range of reactions it can undergo.

In conclusion, 11-bromo-1-undecene is an important chemical in organic synthesis, particularly in the production of functionalized polymers and specialty chemicals. Its bromo group provides reactivity that is exploited in a range of chemical processes, making it a versatile tool for both industrial and research applications. As a precursor to more complex molecules, it continues to play a role in the development of new materials and chemical products.

References

2011. Click Chemistry-Based Functionalization on Non-Oxidized Silicon Substrates. Chemistry - An Asian Journal, 6(9).
DOI: 10.1002/asia.201100294

2012. Iodine(III)-Promoted Intermolecular Diamination of Alkenes. Chemistry - An Asian Journal, 7(3).
DOI: 10.1002/asia.201101025

2024. Inclusion complex-based multifunctional polyurethane antibacterial coatings with excellent mechanical and thermal properties. Journal of Coatings Technology and Research, 21(2).
DOI: 10.1007/s11998-023-00892-2