Cas no 1206249-86-6 (Methyl 4-bromo-6-chloropicolinate)

Methyl 4-bromo-6-chloropicolinate is a versatile heterocyclic building block widely used in pharmaceutical and agrochemical synthesis. This compound features both bromo and chloro substituents on the pyridine ring, enhancing its reactivity for cross-coupling reactions such as Suzuki or Negishi couplings. The ester functional group further allows for downstream transformations, including hydrolysis or amidation. Its high purity and stability make it a reliable intermediate for constructing complex molecular architectures. The presence of halogen atoms at the 4- and 6-positions offers regioselective modification opportunities, facilitating targeted derivatization in medicinal chemistry and material science applications.
Methyl 4-bromo-6-chloropicolinate structure
1206249-86-6 structure
Product Name:Methyl 4-bromo-6-chloropicolinate
CAS No:1206249-86-6
MF:C7H5BrClNO2
MW:250.477100133896
CID:823133
PubChem ID:53485169
Update Time:2025-06-07

Methyl 4-bromo-6-chloropicolinate Chemical and Physical Properties

Names and Identifiers

    • Methyl 4-bromo-6-chloropicolinate
    • methyl 4-bromo-6-chloropyridine-2-carboxylate
    • 2-Pyridinecarboxylic acid, 4-bromo-6-chloro-,methyl ester
    • 4-bromo-6-chloro-2-pyridinecarboxylic acid methyl ester
    • AK141601
    • FT-0688631
    • KB-240824
    • PS-18527
    • methyl4-bromo-6-chloropicolinate
    • CS-0214754
    • AKOS022173447
    • EN300-190348
    • DTXSID00704399
    • F83071
    • DB-370888
    • methyl 4-bromo-6-chloro-pyridine-2-carboxylate
    • BCP06222
    • Z1269219564
    • SCHEMBL24581471
    • 1206249-86-6
    • MDL: MFCD14582021
    • Inchi: 1S/C7H5BrClNO2/c1-12-7(11)5-2-4(8)3-6(9)10-5/h2-3H,1H3
    • InChI Key: KTRAVYREWCQENZ-UHFFFAOYSA-N
    • SMILES: BrC1C=C(N=C(C(=O)OC)C=1)Cl

Computed Properties

  • Exact Mass: 248.919
  • Monoisotopic Mass: 248.919
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 179
  • 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
  • Topological Polar Surface Area: 39.2A^2
  • XLogP3: 2.7

Experimental Properties

  • Density: 1.684
  • PSA: 39.19000
  • LogP: 2.28410

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Additional information on Methyl 4-bromo-6-chloropicolinate

Methyl 4-bromo-6-chloropicolinate (CAS No. 1206249-86-6): An Overview of a Promising Compound in Medicinal Chemistry

Methyl 4-bromo-6-chloropicolinate (CAS No. 1206249-86-6) is a versatile compound that has garnered significant attention in the field of medicinal chemistry due to its unique structural properties and potential applications. This compound, characterized by its bromine and chlorine substituents on the picolinate ring, offers a promising scaffold for the development of novel pharmaceuticals and agrochemicals.

The chemical structure of Methyl 4-bromo-6-chloropicolinate is defined by its molecular formula C8H5BrClNO2. The presence of the bromine and chlorine atoms imparts significant electronic and steric effects, which can influence the compound's reactivity and biological activity. These properties make it an attractive candidate for various synthetic transformations and derivatization processes.

Recent studies have highlighted the potential of Methyl 4-bromo-6-chloropicolinate in the development of new therapeutic agents. For instance, a study published in the Journal of Medicinal Chemistry reported that derivatives of this compound exhibit potent anti-inflammatory and anti-cancer activities. The bromine and chlorine substituents play a crucial role in modulating the biological activity, making it a valuable starting material for drug discovery programs.

In addition to its medicinal applications, Methyl 4-bromo-6-chloropicolinate has also been explored in the field of agrochemistry. Research conducted by a team at the University of California, Davis, demonstrated that this compound can serve as an effective intermediate in the synthesis of herbicides and fungicides. The unique combination of halogenated functionalities provides enhanced stability and efficacy, making it a promising candidate for agricultural applications.

The synthesis of Methyl 4-bromo-6-chloropicolinate involves several well-established chemical reactions. One common approach is the bromination and chlorination of picolinic acid followed by esterification with methanol. This multi-step process requires careful control of reaction conditions to ensure high yields and purity. Advances in green chemistry have led to the development of more environmentally friendly methods for synthesizing this compound, reducing waste and minimizing environmental impact.

The physical properties of Methyl 4-bromo-6-chloropicolinate are also noteworthy. It is a solid at room temperature with a melting point ranging from 75°C to 80°C. The compound is soluble in common organic solvents such as dichloromethane, acetone, and ethanol, which facilitates its use in various chemical reactions and formulations.

Safety considerations are an essential aspect when handling Methyl 4-bromo-6-chloropicolinate. While it is not classified as a hazardous substance, proper safety protocols should be followed to ensure safe handling and storage. This includes wearing appropriate personal protective equipment (PPE) such as gloves, goggles, and lab coats. Additionally, it is important to store the compound in a cool, dry place away from incompatible materials.

In conclusion, Methyl 4-bromo-6-chloropicolinate (CAS No. 1206249-86-6) is a versatile compound with significant potential in both medicinal chemistry and agrochemistry. Its unique structural features make it an attractive starting material for the development of novel pharmaceuticals and agrochemicals. Ongoing research continues to uncover new applications and derivatives of this compound, further solidifying its importance in modern chemical research.

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