Cas no 547740-43-2 (2-tert-butoxy-6-chloropyridine)

2-tert-Butoxy-6-chloropyridine is a versatile intermediate in organic synthesis, particularly valued for its reactive chloropyridine core and sterically hindered tert-butoxy group. The chlorine atom at the 6-position facilitates nucleophilic substitution reactions, making it useful in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The tert-butoxy substituent enhances stability and influences regioselectivity in further functionalization. This compound is commonly employed in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, due to its compatibility with transition metal catalysts. Its well-defined reactivity profile and stability under various conditions make it a reliable building block for complex heterocyclic frameworks.
2-tert-butoxy-6-chloropyridine structure
547740-43-2 structure
Product Name:2-tert-butoxy-6-chloropyridine
CAS No:547740-43-2
MF:C9H12ClNO
MW:185.650681495667
CID:942798
PubChem ID:24885326
Update Time:2025-10-28

2-tert-butoxy-6-chloropyridine Chemical and Physical Properties

Names and Identifiers

    • 2-tert-butoxy-6-chloropyridine
    • 2-chloro-6-[(2-methylpropan-2-yl)oxy]pyridine
    • 2-(tert-butoxy)-6-chloropyridine
    • 2-tert-butoxy-6-chloro-pyridine
    • 676721_ALDRICH
    • ACMC-20anmt
    • AG-F-90985
    • AGN-PC-00J90I
    • CTK1G8646
    • KB-232212
    • Pyridine, 2-chloro-6-(1,1-dimethylethoxy)-
    • 547740-43-2
    • XWA74043
    • AKOS012896398
    • 2-tert-Butoxy-6-chloropyridine, 97%
    • DA-04979
    • A853242
    • DTXSID00475193
    • SCHEMBL7898210
    • MFCD08705263
    • G86063
    • MDL: MFCD08705263
    • Inchi: 1S/C9H12ClNO/c1-9(2,3)12-8-6-4-5-7(10)11-8/h4-6H,1-3H3
    • InChI Key: PLDRTFJRLUKTTA-UHFFFAOYSA-N
    • SMILES: ClC1=CC=CC(=N1)OC(C)(C)C

Computed Properties

  • Exact Mass: 185.06086
  • Monoisotopic Mass: 185.0607417g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 144
  • 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: 3.2
  • Topological Polar Surface Area: 22.1?2

Experimental Properties

  • Density: 1.076?g/mL?at 25?°C
  • Flash Point: Fahrenheit: 172.4 ° f
    Celsius: 78 ° c
  • PSA: 22.12

2-tert-butoxy-6-chloropyridine Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H302-H319
  • Warning Statement: P305+P351+P338
  • Hazardous Material transportation number:NA 1993 / PGIII
  • WGK Germany:3
  • Hazard Category Code: 22-36
  • Safety Instruction: 26
  • Hazardous Material Identification: Xn
  • Risk Phrases:22-36

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2-tert-butoxy-6-chloropyridine Related Literature

Additional information on 2-tert-butoxy-6-chloropyridine

Introduction to 2-tert-butoxy-6-chloropyridine (CAS No. 547740-43-2)

2-tert-butoxy-6-chloropyridine, identified by the chemical identifier CAS No. 547740-43-2, is a significant compound in the realm of pharmaceutical and agrochemical research. This pyridine derivative features a chloro substituent at the 6-position and a tert-butoxy group at the 2-position, making it a versatile intermediate in synthetic chemistry. The unique structural attributes of this compound have garnered attention for its potential applications in drug discovery and material science.

The tert-butoxy group enhances the stability of the pyridine ring, making it more resistant to nucleophilic attack, while the chloro substituent provides a reactive site for further functionalization. These properties make 2-tert-butoxy-6-chloropyridine a valuable building block in the synthesis of more complex molecules. Recent advancements in medicinal chemistry have highlighted its role in developing novel therapeutic agents, particularly in addressing neurological and inflammatory disorders.

In recent years, researchers have been exploring the pharmacological potential of pyridine derivatives, and 2-tert-butoxy-6-chloropyridine has emerged as a key intermediate in several high-profile studies. For instance, studies have demonstrated its utility in synthesizing kinase inhibitors, which are crucial for treating cancers and autoimmune diseases. The compound’s ability to modulate enzyme activity while maintaining structural integrity has made it a focal point in drug design.

One of the most compelling aspects of 2-tert-butoxy-6-chloropyridine is its role in developing small-molecule probes for biochemical pathways. Researchers have leveraged its reactivity to create tools that can interact with specific targets within cell signaling networks. These probes have provided invaluable insights into disease mechanisms, paving the way for more targeted and effective treatments. The compound’s versatility has also been exploited in designing ligands for G-protein coupled receptors (GPCRs), which are involved in a wide range of physiological processes.

The agrochemical industry has not been left behind in exploring the applications of 2-tert-butoxy-6-chloropyridine. Its structural motifs are found in several herbicides and fungicides that enhance crop protection by inhibiting pathogenic fungi and weed growth. The stability conferred by the tert-butoxy group ensures that these compounds remain effective over extended periods, improving agricultural yields.

From a synthetic chemistry perspective, 2-tert-butoxy-6-chloropyridine serves as a precursor for more complex heterocycles. Its reactivity allows for further functionalization through cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, enabling the construction of diverse molecular frameworks. These advances have opened new avenues for creating novel materials with applications ranging from electronics to pharmaceuticals.

The safety profile of 2-tert-butoxy-6-chloropyridine is another critical consideration. While it is not classified as hazardous under standard conditions, proper handling protocols must be followed to ensure worker safety. Its stability under various conditions makes it suitable for industrial-scale synthesis, provided that appropriate storage and handling measures are implemented.

In conclusion, 2-tert-butoxy-6-chloropyridine (CAS No. 547740-43-2) is a multifaceted compound with significant implications across multiple scientific disciplines. Its unique structural features and reactivity make it an indispensable tool in pharmaceutical research, agrochemical development, and synthetic chemistry. As our understanding of its properties continues to evolve, so too will its applications, driving innovation in science and technology.

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