Cas no 1864690-54-9 (1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile)

1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile is a brominated pyrimidine derivative featuring a cyclobutane-carbonitrile moiety, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The bromine substitution at the 5-position enhances its reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, facilitating further functionalization. The cyclobutane ring contributes to structural rigidity, potentially improving binding affinity in target molecules. This compound is particularly useful in medicinal chemistry for the development of kinase inhibitors and other biologically active compounds. Its high purity and well-defined structure ensure consistent performance in synthetic applications. Proper handling under inert conditions is recommended due to its sensitivity.
1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile structure
1864690-54-9 structure
Product Name:1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile
CAS No:1864690-54-9
MF:C9H8BrN3
MW:238.083920478821
CID:5901807
PubChem ID:130544247
Update Time:2025-06-13

1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 1864690-54-9
    • 1-(5-bromopyrimidin-2-yl)cyclobutane-1-carbonitrile
    • EN300-1911996
    • 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile
    • Inchi: 1S/C9H8BrN3/c10-7-4-12-8(13-5-7)9(6-11)2-1-3-9/h4-5H,1-3H2
    • InChI Key: GJGRRDZAJWTLQI-UHFFFAOYSA-N
    • SMILES: BrC1C=NC(C2(C#N)CCC2)=NC=1

Computed Properties

  • Exact Mass: 236.99016g/mol
  • Monoisotopic Mass: 236.99016g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 233
  • 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: 1.5
  • Topological Polar Surface Area: 49.6?2

1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile Pricemore >>

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Additional information on 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile

Comprehensive Overview of 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile (CAS No. 1864690-54-9)

In the realm of pharmaceutical intermediates and fine chemicals, 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile (CAS No. 1864690-54-9) has emerged as a compound of significant interest. This brominated pyrimidine derivative is widely utilized in the synthesis of novel drug candidates, particularly in the fields of oncology and antiviral research. Its unique cyclobutane-carbonitrile structure offers versatile reactivity, making it a valuable building block for medicinal chemists.

The growing demand for high-purity pharmaceutical intermediates has propelled research into compounds like 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile. Recent studies highlight its potential as a key precursor in the development of kinase inhibitors, a class of therapeutics that has gained tremendous attention in cancer treatment. The presence of both bromine and nitrile functional groups in its molecular structure enables diverse chemical transformations, allowing researchers to explore new synthetic pathways.

From a synthetic chemistry perspective, the 5-bromopyrimidine moiety in this compound serves as an excellent leaving group for nucleophilic aromatic substitution reactions. This characteristic makes CAS 1864690-54-9 particularly valuable for constructing complex heterocyclic systems. The cyclobutane ring contributes to the three-dimensionality of resulting molecules, an increasingly important factor in drug design as the pharmaceutical industry moves beyond flat aromatic systems.

Recent advancements in cross-coupling reactions have further enhanced the utility of 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile. The compound participates efficiently in Buchwald-Hartwig aminations and Suzuki-Miyaura couplings, enabling the rapid assembly of diverse molecular architectures. These transformations are particularly relevant in the context of fragment-based drug discovery, where efficient coupling of small molecular fragments is crucial.

The stability profile of 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile makes it suitable for various storage conditions, though it's recommended to maintain it under inert atmosphere at low temperatures for long-term preservation. Analytical data suggests that the compound maintains excellent purity even after extended storage periods, a critical factor for pharmaceutical applications where impurity control is paramount.

In the context of green chemistry initiatives, researchers are exploring more sustainable synthetic routes to access 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile. Recent publications have demonstrated successful approaches using catalytic bromination methods that reduce halogen waste, addressing one of the key environmental concerns in pharmaceutical manufacturing.

The compound's role in proteolysis targeting chimera (PROTAC) development has recently come into focus. Its ability to serve as a linker component between target-binding and E3 ligase-binding moieties makes CAS 1864690-54-9 particularly valuable in this cutting-edge therapeutic modality. This application aligns with current trends in targeted protein degradation, one of the most exciting areas in drug discovery today.

Quality control of 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile typically involves advanced analytical techniques including HPLC, NMR spectroscopy, and mass spectrometry. These methods ensure the compound meets the stringent purity requirements of pharmaceutical applications, where even trace impurities can significantly impact biological activity.

As the pharmaceutical industry continues to emphasize structure-activity relationship studies, the three-dimensional character imparted by the cyclobutane ring in this compound offers distinct advantages. This feature is particularly relevant in addressing current challenges in drug discovery, such as improving target selectivity and reducing off-target effects.

The future outlook for 1-(5-Bromopyrimidin-2-yl)cyclobutane-1-carbonitrile appears promising, with potential applications extending beyond traditional small molecule drugs. Its utility in bioconjugation chemistry and chemical biology probes represents exciting new directions for research. As synthetic methodologies continue to evolve, this compound is likely to play an increasingly important role in the development of next-generation therapeutics.

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