Cas no 1174028-22-8 (methyl 5-bromo-6-methylnicotinate)

Methyl 5-bromo-6-methylnicotinate is a brominated methylnicotinate derivative with applications in pharmaceutical and agrochemical synthesis. As a versatile building block, it features a reactive bromo substituent at the 5-position and an ester group at the 3-position, enabling further functionalization through cross-coupling or nucleophilic substitution reactions. The 6-methyl group enhances steric and electronic properties, influencing reactivity in heterocyclic transformations. This compound is particularly valuable in medicinal chemistry for constructing pyridine-based scaffolds. Its high purity and stability under standard conditions make it suitable for precise synthetic applications. Proper handling under inert conditions is recommended due to its sensitivity to moisture and light.
methyl 5-bromo-6-methylnicotinate structure
1174028-22-8 structure
Product Name:methyl 5-bromo-6-methylnicotinate
CAS No:1174028-22-8
MF:C8H8BrNO2
MW:230.058621406555
MDL:MFCD19440397
CID:2116720
Update Time:2025-10-30

methyl 5-bromo-6-methylnicotinate Chemical and Physical Properties

Names and Identifiers

    • methyl 5-bromo-6-methylnicotinate
    • 5-Bromo-6-methyl-nicotinic acid methyl ester
    • MDL: MFCD19440397
    • Inchi: 1S/C8H8BrNO2/c1-5-7(9)3-6(4-10-5)8(11)12-2/h3-4H,1-2H3
    • InChI Key: AOSWEDIDPYRZRA-UHFFFAOYSA-N
    • SMILES: BrC1=CC(C(=O)OC)=CN=C1C

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2

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Additional information on methyl 5-bromo-6-methylnicotinate

Recent Advances in the Application of Methyl 5-Bromo-6-methylnicotinate (CAS: 1174028-22-8) in Chemical Biology and Pharmaceutical Research

Methyl 5-bromo-6-methylnicotinate (CAS: 1174028-22-8) has emerged as a key building block in medicinal chemistry and drug discovery due to its versatile reactivity and structural features. Recent studies have highlighted its importance as a precursor for the synthesis of various biologically active compounds, particularly in the development of kinase inhibitors and other therapeutic agents targeting cancer and inflammatory diseases.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of methyl 5-bromo-6-methylnicotinate in the synthesis of novel Bruton's tyrosine kinase (BTK) inhibitors. The researchers utilized this compound as a starting material to develop a series of potent and selective BTK inhibitors with improved pharmacokinetic properties. The bromo and ester functional groups allowed for efficient derivatization through cross-coupling reactions and subsequent transformations.

In the field of agrochemical research, methyl 5-bromo-6-methylnicotinate has shown promise as an intermediate for developing new generation pesticides. A recent patent application (WO2023057421) disclosed its use in creating neonicotinoid analogs with enhanced insecticidal activity and reduced environmental impact. The structural flexibility of this compound enables modifications that can fine-tune the biological activity and physicochemical properties of the final products.

Significant progress has been made in optimizing synthetic routes for methyl 5-bromo-6-methylnicotinate. A 2024 publication in Organic Process Research & Development reported an improved, scalable synthesis with higher yields and reduced environmental footprint. The new protocol employs catalytic C-H bromination and minimizes the use of hazardous reagents, addressing both economic and sustainability concerns in industrial production.

Recent pharmacological studies have explored the metabolic fate of methyl 5-bromo-6-methylnicotinate-derived compounds. Research published in Drug Metabolism and Disposition (2024) investigated the esterase-mediated hydrolysis of related prodrugs, providing valuable insights for designing more stable derivatives with optimized drug delivery characteristics.

The compound's potential in PET radiopharmaceutical development has also been recognized. A research group at Massachusetts General Hospital recently reported (Journal of Nuclear Medicine, 2024) the successful incorporation of [11C]-labeled methyl 5-bromo-6-methylnicotinate derivatives as imaging probes for neuroinflammation, demonstrating its versatility beyond traditional small molecule drug development.

Ongoing research continues to uncover new applications for methyl 5-bromo-6-methylnicotinate in chemical biology. Its unique structural features make it particularly valuable for fragment-based drug discovery and the development of targeted protein degraders (PROTACs), as evidenced by several recent preclinical studies in oncology and neurodegenerative diseases.

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