Cas no 1142195-70-7 (4-Bromo-2-tert-butylpyrimidine)

4-Bromo-2-tert-butylpyrimidine is a halogenated pyrimidine derivative featuring a bromine substituent at the 4-position and a tert-butyl group at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The bromine atom enhances reactivity for cross-coupling reactions, such as Suzuki or Stille couplings, enabling efficient derivatization. The sterically hindered tert-butyl group contributes to stability and can influence regioselectivity in subsequent transformations. Its well-defined structure and high purity make it suitable for precision synthesis. The compound is typically handled under inert conditions due to its sensitivity to moisture and air.
4-Bromo-2-tert-butylpyrimidine structure
1142195-70-7 structure
Product Name:4-Bromo-2-tert-butylpyrimidine
CAS No:1142195-70-7
MF:C8H11BrN2
MW:215.090340852737
CID:4572576
PubChem ID:45787597
Update Time:2025-05-20

4-Bromo-2-tert-butylpyrimidine Chemical and Physical Properties

Names and Identifiers

    • 4-bromo-2-tert-butylpyrimidine
    • 4-bromo-2-(tert-butyl)pyrimidine
    • Pyrimidine, 4-bromo-2-(1,1-dimethylethyl)-
    • NE58089
    • 4-Bromo-2-tert-butylpyrimidine
    • Inchi: 1S/C8H11BrN2/c1-8(2,3)7-10-5-4-6(9)11-7/h4-5H,1-3H3
    • InChI Key: XUJUVKJZXXPNFM-UHFFFAOYSA-N
    • SMILES: BrC1=CC=NC(C(C)(C)C)=N1

Computed Properties

  • Exact Mass: 214.01056 g/mol
  • Monoisotopic Mass: 214.01056 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 131
  • 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: 2.9
  • Topological Polar Surface Area: 25.8
  • Molecular Weight: 215.09

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Additional information on 4-Bromo-2-tert-butylpyrimidine

Professional Introduction to 4-Bromo-2-tert-butylpyrimidine (CAS No. 1142195-70-7)

4-Bromo-2-tert-butylpyrimidine, with the chemical identifier CAS No. 1142195-70-7, is a significant compound in the field of pharmaceutical and agrochemical research. This heterocyclic aromatic brominated derivative has garnered considerable attention due to its versatile applications in synthetic chemistry and medicinal chemistry. The presence of both bromine and a bulky tert-butyl group on the pyrimidine ring imparts unique reactivity and steric properties, making it a valuable intermediate in the development of novel bioactive molecules.

The compound's structure, featuring a pyrimidine core substituted at the 4-position with a bromine atom and at the 2-position with a tert-butyl group, contributes to its utility in various chemical transformations. The bromine atom serves as a handle for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura, Stille, or Buchwald-Hartwig couplings, which are pivotal in constructing complex molecular architectures. Meanwhile, the tert-butyl group enhances lipophilicity and metabolic stability, attributes that are highly desirable in drug design.

In recent years, 4-Bromo-2-tert-butylpyrimidine has been extensively explored in the synthesis of small-molecule inhibitors targeting various biological pathways. For instance, its incorporation into kinase inhibitors has shown promise in preclinical studies. The pyrimidine scaffold is a common motif in pharmacophores due to its ability to interact with biological targets through hydrogen bonding and hydrophobic interactions. The brominated derivative, in particular, has been utilized to develop compounds that modulate protein-protein interactions and enzyme activity.

One notable application of 4-Bromo-2-tert-butylpyrimidine is in the development of antiviral agents. The compound's structural features allow for the design of molecules that interfere with viral replication cycles. Researchers have leveraged its reactivity to create analogs that exhibit inhibitory effects on viral enzymes such as polymerases and proteases. These efforts align with ongoing global initiatives to discover novel therapeutics against emerging infectious diseases.

The agrochemical sector also benefits from the use of 4-Bromo-2-tert-butylpyrimidine as a key intermediate in the synthesis of crop protection agents. Its structural motifs are found in several herbicides and fungicides that enhance agricultural productivity by controlling unwanted plant growth and fungal infections. The compound's stability under environmental conditions makes it suitable for formulations that require prolonged efficacy.

Advances in computational chemistry have further enhanced the utility of 4-Bromo-2-tert-butylpyrimidine. Molecular modeling studies have provided insights into its interactions with biological targets, aiding in the rational design of more potent and selective inhibitors. These computational approaches are increasingly integrated into drug discovery pipelines, streamlining the identification of lead compounds.

The synthesis of 4-Bromo-2-tert-butylpyrimidine itself is an area of active research. Recent methodologies have focused on optimizing reaction conditions to improve yield and purity while minimizing environmental impact. Green chemistry principles are being applied to develop more sustainable synthetic routes, including catalytic processes that reduce waste and energy consumption.

Future directions in the study of 4-Bromo-2-tert-butylpyrimidine include exploring its potential in other therapeutic areas such as oncology and neurology. The compound's structural flexibility allows for derivatization into diverse scaffolds that can target specific disease-related pathways. Collaborative efforts between academia and industry are essential to translate these findings into clinical applications.

In conclusion, 4-Bromo-2-tert-butylpyrimidine (CAS No. 1142195-70-7) is a multifaceted compound with broad applications in pharmaceuticals and agrochemicals. Its unique structural features enable its use as a building block for synthesizing bioactive molecules targeting various diseases. As research continues to uncover new therapeutic possibilities, this compound will remain a cornerstone in medicinal chemistry innovation.

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