Production Method 1

75927-49-0

183438-24-6

883901-68-6

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Dichloromethane ,  1,4-Dioxane ,  Water ;  85 °C

Reference

Discovery and in vivo evaluation of alcohol-containing benzothiazoles as potent dual-targeting bacterial DNA supercoiling inhibitors

Palmer, James T.; et al, Bioorganic & Medicinal Chemistry Letters, 2014, 24(17), 4215-4222

5-bromo-2-ethenylpyrimidine Raw materials

• Vinylboronic Acid Pinacol Ester
• 5-Bromo-2-iodopyrimidine

5-bromo-2-ethenylpyrimidine Preparation Products

• 5-bromo-2-ethenylpyrimidine (883901-68-6)

• 1. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877
• 2. An all-solid-state asymmetric device based on a polyaniline hydrogel for a high energy flexible supercapacitor?
  Hamid Heydari,Mohammad B. Gholivand New J. Chem., 2017,41, 237-244
• 3. An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins?
  Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois Mathey Dalton Trans., 2019,48, 5523-5526
• 4. Acenaphthenic hopanoids, a novel series of aromatised
  Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre Albrecht Chem. Commun., 2001, 1976-1977
• 5. An apparatus for testing water by measurement of its electrical conductivity
  Analyst, 1912,37, 538-543

5-Bromo-2-ethenylpyrimidine (CAS No. 883901-68-6): A Versatile Building Block in Organic Synthesis

5-Bromo-2-ethenylpyrimidine (CAS No. 883901-68-6) is a highly valuable heterocyclic compound that has gained significant attention in pharmaceutical and materials science research. This brominated pyrimidine derivative serves as a crucial intermediate in the synthesis of various biologically active molecules and functional materials. The presence of both bromo and ethenyl functional groups on the pyrimidine ring makes it particularly useful for cross-coupling reactions and polymerization processes.

Recent trends in medicinal chemistry have shown increased interest in 5-substituted pyrimidine compounds, with researchers frequently searching for "pyrimidine-based drug discovery" and "bromopyrimidine synthetic applications." The compound's molecular structure (C6H5BrN2) offers excellent opportunities for structural modification, making it a versatile building block in organic synthesis. Its molecular weight of 185.02 g/mol and balanced lipophilicity contribute to its widespread use in drug development programs.

The synthetic utility of 5-bromo-2-ethenylpyrimidine stems from its ability to participate in various chemical transformations. Common search queries like "Heck reaction with bromopyrimidines" and "Suzuki coupling using 5-bromo-2-ethenylpyrimidine" reflect the compound's importance in modern synthetic methodologies. The vinyl group at the 2-position enables polymerization reactions, while the bromine atom at the 5-position serves as an excellent leaving group for nucleophilic aromatic substitution.

In pharmaceutical applications, 5-bromo-2-ethenylpyrimidine derivatives have shown promise in addressing current research challenges. Popular search terms such as "pyrimidine kinase inhibitors" and "small molecule drug candidates 2023" demonstrate the ongoing relevance of this compound class. The molecule's structural features allow for the development of potential therapeutic agents targeting various disease pathways, particularly in oncology and antiviral research.

Material scientists have also explored 5-bromo-2-ethenylpyrimidine for creating advanced functional materials. With growing interest in "organic electronic materials" and "conjugated polymers for optoelectronics," this compound serves as a valuable monomer for constructing π-conjugated systems. The ethenyl group facilitates polymerization, while the pyrimidine ring contributes to electron-deficient character in the resulting materials.

The commercial availability of 5-bromo-2-ethenylpyrimidine (CAS 883901-68-6) has increased significantly in recent years, as evidenced by search trends for "buy 5-bromo-2-vinylpyrimidine" and "suppliers of brominated pyrimidine derivatives." The compound typically appears as a white to off-white crystalline powder with good stability under standard storage conditions. Its purity is crucial for synthetic applications, with most suppliers offering material at ≥95% or ≥98% purity levels.

From a safety perspective, proper handling of 5-bromo-2-ethenylpyrimidine requires standard laboratory precautions. While not classified as hazardous under normal conditions, researchers frequently search for "pyrimidine compound safety data" and "handling brominated heterocycles." The compound should be stored in a cool, dry place away from strong oxidizing agents, with appropriate personal protective equipment used during handling.

The future outlook for 5-bromo-2-ethenylpyrimidine applications appears promising, particularly in emerging fields like "click chemistry in drug discovery" and "metal-organic frameworks construction." As synthetic methodologies continue to advance, this compound's versatility ensures its ongoing relevance in both academic and industrial settings. The growing number of publications and patents referencing CAS 883901-68-6 confirms its importance in contemporary chemical research.

For researchers working with 5-bromo-2-ethenylpyrimidine, understanding its spectroscopic properties is essential. Common analytical techniques include 1H NMR (typically showing characteristic vinyl protons around δ 5.5-6.5 ppm), 13C NMR, and mass spectrometry. The compound's UV-Vis absorption spectrum often shows maxima in the 250-300 nm range, making it suitable for various photophysical studies.

In conclusion, 5-bromo-2-ethenylpyrimidine (CAS No. 883901-68-6) represents a strategically important compound in modern organic synthesis. Its dual functionality as both a brominated aromatic and vinyl-substituted heterocycle enables diverse chemical transformations, addressing current research needs in medicinal chemistry and materials science. As evidenced by search trends and publication activity, this compound continues to play a vital role in developing innovative solutions across multiple scientific disciplines.

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