1,8-Dibromooctane: Difference between revisions

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<br>= 1,8-Dibromooctane =
{{Chembox
| verifiedfields = changed
| verifiedrevid = 477239123
| ImageFile = 1,8-Dibromooctane.svg
| ImageSize = 200px
| ImageAlt = Structural formula of 1,8-Dibromooctane
| IUPACName = 1,8-Dibromooctane
| OtherNames = Octamethylene dibromide
| Section1 = {{Chembox Identifiers
  | CASNo = 4549-32-0
  | PubChem = 10466
  | ChemSpiderID = 10032
  | UNII = 8X5F9Q0V7R
  | SMILES = BrCCCCCCCCBr
  | InChI = 1S/C8H16Br2/c9-7-5-3-1-2-4-6-8-10/h1-8H2
  | InChIKey = ZJHUBQJZVQIKNF-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
  | C = 8
  | H = 16
  | Br = 2
  | Appearance = Colorless liquid
  | Density = 1.44 g/cm³
  | MeltingPt = -2 °C
  | BoilingPt = 243 °C
}}
}}


'''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.
'''1,8-Dibromooctane''' is an organic compound with the formula C₈H₁₆Br₂. It is a colorless liquid that is used in organic synthesis, particularly in the preparation of polymers and as a reagent in the formation of other chemical compounds.


== Chemical Structure and Properties ==
==Synthesis and Reactions==
1,8-Dibromooctane can be synthesized by the bromination of 1-octene or by the reaction of 1,8-octanediol with hydrobromic acid. The compound is a useful intermediate in the synthesis of various organic compounds, including [[macrocycles]] and [[crown ethers]].


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.
In organic synthesis, 1,8-dibromooctane is often used as a bifunctional alkylating agent. It can react with nucleophiles to form a variety of products, including cyclic compounds when used in intramolecular reactions.


* '''Molecular Formula''': C₈H₁₆Br₂
==Applications==
* '''Molar Mass''': 271.02 g/mol
1,8-Dibromooctane is used in the production of [[polymers]] and as a cross-linking agent. It is also employed in the synthesis of [[surfactants]] and other specialty chemicals. Its ability to form long carbon chains with terminal bromine atoms makes it valuable in the preparation of [[macrocyclic compounds]] and other complex structures.
* '''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 ==
==Safety and Handling==
As with many brominated compounds, 1,8-dibromooctane should be handled with care. It is important to use appropriate personal protective equipment, such as gloves and goggles, when working with this chemical. It should be stored in a cool, dry place, away from sources of ignition and incompatible materials.


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.
==Also see==
* [[Bromination]]
* [[Alkylation]]
* [[Organic synthesis]]
* [[Polymer chemistry]]


== Applications ==
{{Organic compounds}}
 
{{Bromine compounds}}
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.


[[Category:Organobromides]]
[[Category:Organobromides]]
[[Category:Alkyl halides]]
[[Category:Alkylating agents]]
[[Category:Chemical compounds]]
[[Category:Reagents for organic chemistry]]

Latest revision as of 02:42, 11 December 2024

Chemical Compound
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PubChem CID
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ChEMBL
Properties
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References

1,8-Dibromooctane is an organic compound with the formula C₈H₁₆Br₂. It is a colorless liquid that is used in organic synthesis, particularly in the preparation of polymers and as a reagent in the formation of other chemical compounds.

Synthesis and Reactions[edit]

1,8-Dibromooctane can be synthesized by the bromination of 1-octene or by the reaction of 1,8-octanediol with hydrobromic acid. The compound is a useful intermediate in the synthesis of various organic compounds, including macrocycles and crown ethers.

In organic synthesis, 1,8-dibromooctane is often used as a bifunctional alkylating agent. It can react with nucleophiles to form a variety of products, including cyclic compounds when used in intramolecular reactions.

Applications[edit]

1,8-Dibromooctane is used in the production of polymers and as a cross-linking agent. It is also employed in the synthesis of surfactants and other specialty chemicals. Its ability to form long carbon chains with terminal bromine atoms makes it valuable in the preparation of macrocyclic compounds and other complex structures.

Safety and Handling[edit]

As with many brominated compounds, 1,8-dibromooctane should be handled with care. It is important to use appropriate personal protective equipment, such as gloves and goggles, when working with this chemical. It should be stored in a cool, dry place, away from sources of ignition and incompatible materials.

Also see[edit]



Organic compounds
General
By element
Polymers
Biomolecules
Related
This organic compounds related article is a stub.



Bromine compounds
Br(−I)
Br(−I,I)
Br(I)
Br(II)
Br(I,V)
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