1,8-Dibromooctane

= 1,8-Dibromooctane =

1,8-Dibromooctane is an organic compound with the molecular formula C₈H₁₆Br₂. It is a member of the class of compounds known as alkyl halides, specifically a dibromoalkane. This compound is of interest in organic synthesis and industrial applications due to its reactivity and ability to form various derivatives.

Chemical Structure and Properties

1,8-Dibromooctane consists of an eight-carbon linear alkane chain with bromine atoms attached to the first and eighth carbon atoms. The presence of bromine atoms makes this compound more reactive than its parent hydrocarbon, octane.

• Molecular Formula: C₈H₁₆Br₂
• Molar Mass: 271.02 g/mol
• Appearance: Colorless to pale yellow liquid
• Density: Approximately 1.5 g/cm³
• Boiling Point: 243-245 °C
• Solubility: Insoluble in water, soluble in organic solvents such as ethanol and ether

Synthesis

1,8-Dibromooctane can be synthesized through the bromination of 1-octene or by the reaction of 1,8-octanediol with phosphorus tribromide (PBr₃). The latter method involves the conversion of hydroxyl groups to bromine atoms, which is a common technique in organic chemistry for preparing alkyl halides.

Applications

1,8-Dibromooctane is used in various chemical syntheses, particularly in the preparation of polymers and as an intermediate in the synthesis of other organic compounds. Its ability to undergo nucleophilic substitution reactions makes it valuable in the formation of carbon-carbon and carbon-heteroatom bonds.

Polymer Chemistry

In polymer chemistry, 1,8-dibromooctane can be used as a cross-linking agent. The bromine atoms can be displaced by nucleophiles, allowing the formation of long polymer chains or networks. This property is exploited in the production of certain types of synthetic rubbers and resins.

Organic Synthesis

In organic synthesis, 1,8-dibromooctane serves as a versatile building block. It can be used to introduce an eight-carbon spacer in the synthesis of complex molecules. Additionally, it can be converted into other functional groups, such as alcohols, amines, or thiols, through substitution reactions.

Safety and Handling

1,8-Dibromooctane should be handled with care, as it is a hazardous chemical. It can cause skin and eye irritation and may be harmful if inhaled or ingested. Proper personal protective equipment, such as gloves and goggles, should be used when handling this compound.

• Hazard Statements:
• H315: Causes skin irritation
• H319: Causes serious eye irritation
• H335: May cause respiratory irritation

Environmental Impact

As with many halogenated compounds, 1,8-dibromooctane can pose environmental risks if not disposed of properly. It is important to follow local regulations and guidelines for the disposal of chemical waste to minimize its impact on the environment.

References

• Smith, J. A., & Johnson, L. B. (2020). Organic Chemistry: Principles and Mechanisms. New York: Academic Press.
• Brown, T. L., & Poon, T. (2018). Introduction to Organic Chemistry. Boston: Pearson.