2,5-Dibromohexane

2,5-Dibromohexane is an organic halogenated hydrocarbon with a six-carbon straight-chain structure. It contains two bromine atoms attached to the 2nd and 5th carbon atoms of the chain. Its molecular formula is C₆H₁₂Br₂, and it typically appears as a colorless to pale yellow liquid.

1. Organic Synthesis Intermediate

   • Used in the synthesis of complex organic molecules.
   • Serves as a precursor for cross-coupling reactions (e.g., Suzuki, Heck reactions) due to the presence of bromide leaving groups.
   • Useful in the preparation of cyclic compounds via intramolecular cyclization.

2. Material Science and Polymer Chemistry

   • Applied in the synthesis of functional polymers or dendrimers.
   • Can act as a cross-linker or spacer molecule in advanced materials.

3. Pharmaceutical and Agrochemical Research

   • Employed in the development of intermediates for drug discovery or agrochemicals.
   • Useful building block in medicinal chemistry for modifying bioactive molecules.

4. Chemical Reagents & Derivatization

   • Utilized in alkylation reactions or as a reagent for introducing brominated alkyl chains into other molecules.

1. Selective Bromination of Hexene Derivatives

   • Using N-Bromosuccinimide (NBS) under radical conditions to selectively introduce bromine at the 2nd and 5th positions.
   • Requires precise control of reaction parameters to ensure regioselectivity.

2. Direct Bromination of Hexane or Alkene Precursors

   • Reaction of hexane or hexene with elemental bromine (Br₂) under UV light or peroxide initiation.
   • This method often requires purification steps to isolate the desired 2,5-dibromo isomer from other by-products.

3. Electrophilic Addition to Dienes

   • If a conjugated diene is available, bromine can be added selectively to form vicinal dibromides, which may be rearranged or further modified.

Molecular Weight:243.97
XLogP3:3.3
Rotatable Bond Count:3
Exact Mass:243.92853
Monoisotopic Mass:241.93058
Heavy Atom Count:8
Complexity:46.5
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes