Cas no 55007-44-8 (2-bromo-2,4,4-trimethylpentan-3-one)

2-Bromo-2,4,4-trimethylpentan-3-one is a brominated ketone compound characterized by its unique molecular structure, featuring a bromine atom at the 2-position and three methyl groups at the 2,4,4-positions. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its sterically hindered structure enhances reactivity in nucleophilic substitution reactions, making it valuable for constructing complex molecular frameworks. The presence of the bromine atom offers a reactive site for further functionalization, while the ketone group provides a handle for subsequent transformations. Its stability under various reaction conditions and high purity make it suitable for precision applications in research and industrial processes.
2-bromo-2,4,4-trimethylpentan-3-one structure
55007-44-8 structure
Product Name:2-bromo-2,4,4-trimethylpentan-3-one
CAS No:55007-44-8
MF:C8H15BrO
MW:207.108102083206
CID:353069
PubChem ID:4147608
Update Time:2025-07-02

2-bromo-2,4,4-trimethylpentan-3-one Chemical and Physical Properties

Names and Identifiers

    • 3-Pentanone, 2-bromo-2,4,4-trimethyl-
    • 2-bromo-2,4,4-trimethylpentan-3-one
    • AKOS024340651
    • 2-BROMO-2,4,4-TRIMETHYL-3-PENTANONE
    • 55007-44-8
    • EN300-358960
    • CS-0247180
    • DTXSID80399909
    • SCHEMBL14976728
    • Inchi: 1S/C8H15BrO/c1-7(2,3)6(10)8(4,5)9/h1-5H3
    • InChI Key: CLUHREPHOLNVFF-UHFFFAOYSA-N
    • SMILES: BrC(C)(C)C(C(C)(C)C)=O

Computed Properties

  • Exact Mass: 206.03065
  • Monoisotopic Mass: 206.031
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 142
  • 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
  • XLogP3: 2.7
  • Topological Polar Surface Area: 17.1?2

Experimental Properties

  • PSA: 17.07

2-bromo-2,4,4-trimethylpentan-3-one Pricemore >>

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Additional information on 2-bromo-2,4,4-trimethylpentan-3-one

Chemical Profile of 2-bromo-2,4,4-trimethylpentan-3-one (CAS No. 55007-44-8)

2-bromo-2,4,4-trimethylpentan-3-one, identified by its Chemical Abstracts Service number (CAS No. 55007-44-8), is a significant compound in the realm of organic synthesis and pharmaceutical chemistry. This ketone derivative features a unique structural configuration that makes it a valuable intermediate in the synthesis of various bioactive molecules. The presence of a bromine substituent at the 2-position enhances its reactivity, making it particularly useful in cross-coupling reactions and as a building block for more complex structures.

The compound belongs to the class of α-bromo ketones, which are widely employed in synthetic organic chemistry due to their versatility in forming new carbon-carbon bonds. The bromo group at the alpha position allows for nucleophilic addition reactions, while the trimethyl substitution pattern at the 4-position provides steric and electronic influences that can modulate reaction outcomes. This combination makes 2-bromo-2,4,4-trimethylpentan-3-one a preferred choice for researchers aiming to construct intricate molecular frameworks.

In recent years, there has been growing interest in the applications of α-bromo ketones in pharmaceutical synthesis. Specifically, compounds with similar structural motifs have been explored as precursors for drug candidates targeting neurological disorders and inflammatory conditions. The reactivity of 2-bromo-2,4,4-trimethylpentan-3-one allows for facile introduction of functional groups via palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura and Heck couplings. These transformations are pivotal in constructing heterocyclic scaffolds that are prevalent in modern medicinal chemistry.

One notable area of research involves the use of 2-bromo-2,4,4-trimethylpentan-3-one in the synthesis of kinase inhibitors. Kinases are enzymes that play critical roles in cell signaling pathways, and their dysregulation is often associated with cancer and inflammatory diseases. By leveraging the compound's brominated ketone core, chemists have developed libraries of small molecules capable of inhibiting specific kinase isoforms. For instance, derivatives of this compound have been investigated for their potential to modulate Janus kinases (JAKs), which are implicated in autoimmune diseases.

The structural features of 2-bromo-2,4,4-trimethylpentan-3-one also make it a suitable candidate for exploring novel synthetic methodologies. Transition-metal catalysis remains a cornerstone of modern organic synthesis, and α-bromo ketones like this one serve as ideal substrates for developing new catalytic systems. Recent advances in photoredox catalysis have enabled the use of visible light to drive C-H activation and functionalization reactions. 2-Bromo-2,4,4-trimethylpentan-3-one has been employed in such reactions to introduce diverse substituents at non-hydrogen positions, expanding the toolkit available to synthetic chemists.

Another emerging application lies in the field of materials science. The unique electronic properties conferred by the bromine substituent and the branched alkyl groups make this compound a potential precursor for liquid crystals or polymers with tailored optical characteristics. Researchers are exploring its incorporation into conjugated polymers used in organic electronics, where precise control over molecular architecture is essential for optimizing charge transport properties.

The industrial significance of 2-bromo-2,4,4-trimethylpentan-3-one is further underscored by its role in agrochemical research. The agrochemical industry continuously seeks novel intermediates to develop more effective pesticides and herbicides. The compound's reactivity allows for the rapid introduction of bioisosteric groups that can enhance binding affinity to biological targets without compromising efficacy. This has led to several patents describing its use in synthesizing next-generation crop protection agents.

In conclusion, 2-bromo-2,4,4-trimethylpentan-3-one (CAS No. 55007-44-8) represents a versatile and highly functional molecule with broad applications across multiple scientific disciplines. Its utility as a synthetic intermediate continues to drive innovation in pharmaceuticals, materials science, and agrochemicals. As research progresses,the full potential of this compound is likely to be uncovered,further solidifying its importance in modern chemical synthesis.

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