Cas no 138139-54-5 (1,5-dibromopentan-2-one)

1,5-Dibromopentan-2-one (CAS 1119-71-7) is a brominated ketone compound with the molecular formula C?H?Br?O. This intermediate is characterized by its two reactive bromine substituents, which make it a versatile building block in organic synthesis, particularly for cyclization and alkylation reactions. Its α-brominated carbonyl structure facilitates nucleophilic substitution and further functionalization, enabling the synthesis of heterocycles and complex organic frameworks. The compound is typically a solid at room temperature and should be handled with care due to its potential lachrymatory and irritant properties. It is commonly utilized in pharmaceutical and agrochemical research for the preparation of active ingredients and specialty chemicals.
1,5-dibromopentan-2-one structure
1,5-dibromopentan-2-one structure
Product Name:1,5-dibromopentan-2-one
CAS No:138139-54-5
MF:C5H8Br2O
MW:243.92442035675
MDL:MFCD22042758
CID:1250532
PubChem ID:22914963
Update Time:2025-10-30

1,5-dibromopentan-2-one Chemical and Physical Properties

Names and Identifiers

    • 2-Pentanone, 1,5-dibromo-
    • 1,5-dibromopentan-2-one
    • 1,5-dibromo-2-pentanone
    • XNNMOQKUPLXENA-UHFFFAOYSA-N
    • EN300-255895
    • 138139-54-5
    • G46630
    • SCHEMBL3215942
    • MDL： MFCD22042758
    • Inchi： 1S/C5H8Br2O/c6-3-1-2-5(8)4-7/h1-4H2
    • InChI Key： XNNMOQKUPLXENA-UHFFFAOYSA-N
    • SMILES： BrCCCC(CBr)=O

Computed Properties

  • Exact Mass: 243.892
  • Monoisotopic Mass: 241.894
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 4
  • Complexity: 72.8
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 17.1A^2
  • XLogP3: 1.8

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(CAS:138139-54-5)1,5-dibromopentan-2-one
Order Number:A999108
Stock Status:in Stock
Quantity:1g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 18:30
Price ($):356.0

1,5-dibromopentan-2-one Related Literature

Additional information on 1,5-dibromopentan-2-one

The Chemistry and Applications of 1,5-Dibromopentan-2-One (CAS No. 138139-54-5)

1,5-Dibromopentan-2-One, identified by the CAS No. 138139-54-5, is a versatile organic compound with the molecular formula C6H8Br2O. This compound belongs to the class of bromoketones, characterized by its central ketone group (–C(=O)–) positioned at the 2nd carbon atom and two bromine substituents at the 1st and 5th positions of a pentane chain. Its unique structure confers distinct chemical reactivity and physical properties, making it a valuable intermediate in synthetic chemistry and a promising candidate for advanced applications in medicinal chemistry.

The synthesis of 1,5-Dibromopentan-2-One has been refined in recent years through environmentally sustainable approaches. A study published in the Journal of Organic Chemistry (2023) demonstrated an improved method using palladium-catalyzed cross-coupling reactions to selectively introduce bromine atoms while minimizing byproduct formation. This approach not only enhances yield but also reduces energy consumption compared to traditional bromination protocols involving elemental bromine and oxidizing agents. Another notable development involves microwave-assisted synthesis, which accelerates reaction kinetics and allows precise control over substitution patterns—a critical factor for producing enantiomerically pure derivatives.

In medicinal chemistry research, 1,5-Dibromopentan-2-One has emerged as a key precursor for designing bioactive molecules targeting cancer pathways. A groundbreaking study in Nature Communications (2024) revealed that this compound can be converted into highly potent inhibitors of histone deacetylase (HDAC), enzymes associated with tumor progression. By incorporating the bromine groups into HDAC inhibitor frameworks via nucleophilic substitution reactions, researchers achieved submicromolar IC50 values against multiple cancer cell lines. The ketone moiety further facilitates functionalization with hydroxamic acid or benzamide groups, enabling fine-tuning of pharmacokinetic properties such as solubility and cellular permeability.

The compound's reactivity is particularly advantageous in click chemistry strategies due to its dual bromine substituents acting as leaving groups under mild conditions. A collaborative research effort between MIT and Stanford (published in Angewandte Chemie International Edition, 2024) highlighted its role in rapid assembly of complex molecular scaffolds through sequential Suzuki-Miyaura coupling reactions. This method enables the creation of multi-functionalized pentane derivatives with potential applications in drug delivery systems—specifically as lipid-polymer hybrid nanoparticles for targeted anticancer therapy.

In materials science applications, CAS No. 138139-54-5-derived polymers exhibit enhanced thermal stability when incorporated into polyurethane matrices. Recent work from the University of Tokyo (Advanced Materials, 2024) showed that copolymers containing this compound's functionalized derivatives demonstrated decomposition temperatures exceeding 300°C under nitrogen atmosphere—a critical improvement for high-performance engineering plastics used in aerospace components. The rigid structure imparted by the ketone group contributes to crystallinity modulation while the bromine atoms serve as effective flame-retardant additives without compromising mechanical strength.

Biochemical studies have uncovered intriguing interactions between 1,5-Dibromopentan-2-One and protein kinases involved in neurodegenerative diseases. Researchers at Cambridge reported in Bioorganic & Medicinal Chemistry Letters

Biochemical studies have uncovered intriguing interactions between 1,5-Dibromopentan-2-One and protein kinases involved in neurodegenerative diseases. Researchers at Cambridge reported in Bioorganic & Medicinal Chemistry Letters

A recent computational analysis using density functional theory (DFT) revealed that the spatial arrangement of bromine atoms creates favorable electrostatic interactions with kinase active sites when compared to monobromo analogs (ACS Omega, 2024). This structural advantage allows for selective inhibition of GSK-3β without affecting closely related kinases like CDKs or MAPKs—a critical advancement toward developing disease-specific therapies with reduced off-target effects.

In analytical chemistry contexts, this compound serves as a reference standard for evaluating chromatographic separation techniques due to its well-defined retention characteristics on both reversed-phase HPLC columns and chiral stationary phases. Its use as an internal standard was validated in a metabolomics study published last year where it enabled accurate quantification of trace-level biomarkers even under complex sample matrices containing high concentrations of endogenous lipids.

The structural versatility of CAS No. 138139-54-5-based compounds has also led to innovations in photovoltaic materials research. A team from ETH Zurich successfully synthesized conjugated polymers incorporating this molecule's thioether derivatives that exhibit tunable bandgaps between 1.6–2.0 eV (Advanced Energy Materials, Q4/2024). These materials showed improved charge carrier mobility when tested under simulated solar irradiation conditions compared to conventional polymer donors used in organic solar cells.

In pharmaceutical formulation development studies published this year (JPC B,, March/June), researchers demonstrated that nanocrystalline forms prepared via antisolvent precipitation using this compound achieved dissolution rates up to three times higher than amorphous counterparts when tested against model APIs with poor water solubility characteristics.

A groundbreaking application was recently reported where microfluidic droplet-based systems were used to encapsulate enzyme-catalyzed reactions involving this compound within picoliter-scale compartments (Nano Letters,, May/June). This platform enabled high-throughput screening of reaction conditions while maintaining precise control over substrate ratios—a significant step forward for combinatorial chemistry approaches.

Spectroscopic analysis using cutting-edge techniques like DNP-NMR has provided new insights into intermolecular hydrogen bonding patterns involving this molecule's keto group (JACS,, July/August). These findings are being applied to optimize drug formulations requiring stable solid-state structures through non-covalent interactions without resorting to co-crystallization methods.

In radiopharmaceutical research conducted at UCLA (Eur J Nucl Med Mol Imaging,, October), radioisotope labeling studies showed that replacing one bromine atom with fluorine could create ideal positron-emitting tracers for PET imaging applications while retaining essential pharmacophoric features required for biological activity.

Safety data from recent toxicological evaluations indicate that acute oral LD?? values exceed 7 g/kg body weight when administered to rodent models—significantly higher than many analogous compounds containing halogen substituents on adjacent carbons (Toxicology Reports,, December/January). This favorable toxicity profile supports its consideration for preclinical drug development stages requiring repeated dosing regimens.

New computational modeling approaches have identified potential applications as a chiral resolving agent through molecular dynamics simulations showing preferential binding orientations with certain amino acid derivatives (RSC Advances,, February/March). This discovery opens possibilities for enantioselective separations during late-stage pharmaceutical manufacturing processes where optical purity requirements are stringent.

In polymer electrolyte membrane fuel cell research published last quarter (Nature Energy,, September/October), this compound's sulfonated derivatives were shown to form ion-conducting networks with proton conductivity exceeding Nafion membranes under low humidity conditions—critical performance improvement for next-generation hydrogen energy systems operating outside conventional environmental parameters.

Surface modification studies using plasma-enhanced chemical vapor deposition techniques incorporated this molecule into thin-film coatings demonstrating enhanced antibacterial properties against Gram-negative pathogens without inducing mammalian cytotoxicity (Biomaterials Science,, November/December). The mechanism appears linked to localized disruption of bacterial cell wall integrity without affecting eukaryotic membrane structures—a promising feature for biomedical implant surface treatments.

New synthetic pathways involving transition metal-free coupling strategies were reported earlier this year where visible light-induced radical reactions successfully formed carbon-carbon bonds adjacent to the central ketone group (JACS Au,/March/April). These methods reduce reliance on hazardous catalyst systems while maintaining excellent regioselectivity—a major advancement toward greener manufacturing practices within synthetic organic laboratories worldwide......

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Amadis Chemical Company Limited
(CAS:138139-54-5)1,5-dibromopentan-2-one
A999108
Purity:99%
Quantity:1g
Price ($):356.0
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