Production Method 1

29682-15-3

845306-08-3

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  0 °C; 10 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  1 h, 0 °C

Reference

Direct C-2 arylation of alkyl 4-thiazolecarboxylates: new insights in synthesis of heterocyclic core of thiopeptide antibiotics

Martin, Thibaut; et al, Organic Letters, 2008, 10(13), 2909-2912

Production Method 2

24424-99-5

30766-11-1

845306-08-3

Reaction Conditions

1.1 Catalysts: 4-(Dimethylamino)pyridine Solvents: Toluene ;  0 °C; 20 h, 50 °C

Reference

Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(VI) catalyst

Akasapu, Siddhartha; et al, Chemical Science, 2019, 10(7), 1971-1975

Tert-Butyl 5-bromopyridine-2-carboxylate Raw materials

• Di-tert-butyl dicarbonate
• Methyl 5-bromopyridine-2-carboxylate
• 5-bromopyridine-2-carboxylic acid

Tert-Butyl 5-bromopyridine-2-carboxylate Preparation Products

• Tert-Butyl 5-bromopyridine-2-carboxylate (845306-08-3)

• 1. Excitation energies from ground-state density-functionals by means of generator coordinates
  A. B. F. da Silva,K. Capelle Phys. Chem. Chem. Phys., 2009,11, 4564-4569
• 2. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 3. Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe?
  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161
• 4. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 5. Emulsion technologies for multicellular tumour spheroid radiation assays?
  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110

Comprehensive Overview of Tert-Butyl 5-bromopyridine-2-carboxylate (CAS No. 845306-08-3): Properties, Applications, and Industry Insights

Tert-Butyl 5-bromopyridine-2-carboxylate (CAS No. 845306-08-3) is a high-value heterocyclic compound widely utilized in pharmaceutical and agrochemical research. This brominated pyridine derivative serves as a critical building block in organic synthesis, particularly in the development of active pharmaceutical ingredients (APIs) and specialty chemicals. Its molecular structure combines a pyridine ring with a tert-butyl ester group and a bromo substituent, offering unique reactivity for cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig amination.

Recent trends in drug discovery have amplified demand for functionalized pyridines like Tert-Butyl 5-bromopyridine-2-carboxylate. Pharmaceutical researchers frequently search for "pyridine-based scaffolds for kinase inhibitors" or "bromopyridine derivatives in medicinal chemistry," reflecting its importance in developing targeted therapies. The compound's CAS No. 845306-08-3 is often queried alongside "high-purity bromopyridine reagents" and "sterically hindered carboxylate protectors" in scientific databases.

From a synthetic perspective, the tert-butyl ester group in 845306-08-3 provides excellent hydrolytic stability during reactions while remaining cleavable under acidic conditions—a property highly valued in peptide synthesis and prodrug design. The 5-bromo position offers a strategic handle for palladium-catalyzed transformations, making this compound indispensable for creating biaryl structures prevalent in modern drug candidates.

Environmental and regulatory considerations have driven innovation around halogenated intermediates. While Tert-Butyl 5-bromopyridine-2-carboxylate requires standard laboratory precautions, its efficient atom economy in synthesis aligns with green chemistry principles. Industry searches for "eco-friendly bromination methods" and "sustainable heterocycle synthesis" demonstrate this evolving focus.

The compound's physicochemical properties—including its crystalline form, solubility profile, and thermal stability—make it particularly suitable for high-throughput screening applications. Analytical chemists frequently examine "HPLC methods for bromopyridine analysis" and "spectroscopic characterization of pyridine carboxylates," underscoring its analytical importance.

In material science, CAS 845306-08-3 has shown promise as a precursor for functionalized polymers and coordination complexes. The tert-butyl group enhances solubility in organic matrices, while the bromine atom facilitates polymer crosslinking. These attributes have sparked interest in "pyridine-containing electronic materials" research.

Quality specifications for Tert-Butyl 5-bromopyridine-2-carboxylate typically emphasize ≥98% purity by NMR analysis, with strict control of heavy metal residues for pharmaceutical applications. The compound's stability under nitrogen atmosphere and compatibility with common anhydrous reaction conditions contribute to its reliable performance in multi-step syntheses.

Emerging applications in bioconjugation chemistry and proteolysis-targeting chimeras (PROTACs) have further expanded the utility of this versatile intermediate. Scientific literature increasingly associates 845306-08-3 with "click chemistry modifications" and "bifunctional linker synthesis," reflecting cutting-edge developments.

From a commercial standpoint, Tert-Butyl 5-bromopyridine-2-carboxylate is available through specialized fine chemical suppliers with custom synthesis options. Procurement specialists often evaluate "bulk pyridine derivative suppliers" and "GMP-grade heterocyclic compounds," indicating its industrial relevance. Proper storage recommendations include desiccated conditions at 2-8°C to maintain optimal stability.

Ongoing research continues to uncover novel applications for this multifunctional compound, particularly in asymmetric catalysis and metal-organic framework (MOF) design. Its balanced combination of steric bulk and electronic effects positions CAS 845306-08-3 as a enduringly valuable tool for molecular innovation across scientific disciplines.

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