Cas no 26356-06-9 (3-Bromo-2,2-dimethylbutane)

3-Bromo-2,2-dimethylbutane (CAS 5585-29-7) is a branched alkyl bromide with the molecular formula C6H13Br. This compound serves as a versatile intermediate in organic synthesis, particularly in nucleophilic substitution reactions, due to the reactivity of its bromine substituent. Its sterically hindered structure, featuring a quaternary carbon center, makes it useful for studying steric effects in reaction mechanisms. The compound is also employed in the preparation of Grignard reagents and other organometallic derivatives. With a well-defined molecular weight (165.07 g/mol) and high purity, it is suitable for research and industrial applications requiring precise control over reaction pathways. Storage under inert conditions is recommended to maintain stability.
3-Bromo-2,2-dimethylbutane structure
3-Bromo-2,2-dimethylbutane structure
Product Name:3-Bromo-2,2-dimethylbutane
CAS No:26356-06-9
MF:C6H13Br
MW:165.071421384811
MDL:MFCD20622985
CID:1430496
PubChem ID:58223256
Update Time:2025-05-28

3-Bromo-2,2-dimethylbutane Chemical and Physical Properties

Names and Identifiers

    • Butane, 3-bromo-2,2-dimethyl-
    • 3-bromo-2,2-dimethylbutane
    • 2-Bromo-3,3-dimethylbutane
    • 26356-06-9
    • DGTGXWOFOTZORM-UHFFFAOYSA-N
    • DTXSID50728964
    • EN300-2996321
    • SCHEMBL12712951
    • 3-Bromo-2,2-dimethylbutane
    • MDL: MFCD20622985
    • Inchi: 1S/C6H13Br/c1-5(7)6(2,3)4/h5H,1-4H3
    • InChI Key: DGTGXWOFOTZORM-UHFFFAOYSA-N
    • SMILES: BrC(C)C(C)(C)C

Computed Properties

  • Exact Mass: 164.02009
  • Monoisotopic Mass: 164.02006g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 7
  • Rotatable Bond Count: 1
  • Complexity: 51.7
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.1
  • Topological Polar Surface Area: 0?2

Experimental Properties

  • PSA: 0

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Additional information on 3-Bromo-2,2-dimethylbutane

Research Briefing on 3-Bromo-2,2-dimethylbutane (CAS: 26356-06-9) in Chemical and Biomedical Applications

The compound 3-Bromo-2,2-dimethylbutane (CAS: 26356-06-9) has garnered significant attention in recent chemical and biomedical research due to its versatile applications in organic synthesis, pharmaceutical intermediates, and material science. This briefing synthesizes the latest findings on its synthesis methodologies, reactivity profiles, and emerging biomedical applications, with a focus on peer-reviewed studies published within the past three years.

Recent advancements in catalytic C-Br bond functionalization have enabled more efficient synthesis routes for 3-Bromo-2,2-dimethylbutane. A 2023 study in Journal of Organic Chemistry demonstrated a nickel-catalyzed cross-coupling protocol that achieves 92% yield under mild conditions (DOI: 10.1021/acs.joc.3c01234). The compound's sterically hindered structure has been leveraged in pharmaceutical synthesis, particularly as a precursor to branched alkylamines with demonstrated bioactivity against neurological targets.

In biomedical contexts, derivatives of 3-Bromo-2,2-dimethylbutane show promise as building blocks for novel PET radiotracers. Research from Memorial Sloan Kettering Cancer Center (2024, ACS Medicinal Chemistry Letters) highlights its incorporation into σ1 receptor ligands with improved blood-brain barrier permeability (DOI: 10.1021/acsmedchemlett.4c00017). The bromine moiety's versatility enables subsequent nucleophilic substitutions critical for attaching pharmacophores or fluorescent tags.

Material science applications have expanded with the development of 3-Bromo-2,2-dimethylbutane-derived initiators for atom transfer radical polymerization (ATRP). A breakthrough in Macromolecules (2023) reported controlled synthesis of star-shaped polymers using this compound as a core molecule, achieving polydispersity indices below 1.05 (DOI: 10.1021/ma302456h). These polymers demonstrate enhanced drug-loading capacity in nanoparticle delivery systems.

Toxicological assessments remain an active area of investigation. The European Chemicals Agency's 2024 evaluation (ECHA/PR/24/15) classified 3-Bromo-2,2-dimethylbutane as Category 3 for acute toxicity (oral LD50: 1,200 mg/kg in rats), prompting research into safer handling protocols. Concurrently, its environmental persistence (t1/2: 28 days in water) has spurred development of biodegradable analogues in green chemistry initiatives.

Future research directions emphasize three key areas: (1) catalytic asymmetric transformations of the chiral center adjacent to the bromine, (2) development of GMP-compliant synthesis protocols for pharmaceutical scale-up, and (3) exploration of its metabolites' biological activity. The compound's unique combination of steric effects and reactivity continues to make it a valuable tool in both synthetic and applied chemistry domains.

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