Cas no 97691-23-1 (2-(Tert-Butyl)-6-chloropyridine)

2-(Tert-Butyl)-6-chloropyridine is a halogenated pyridine derivative featuring a tert-butyl substituent at the 2-position and a chlorine atom at the 6-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The tert-butyl group enhances steric hindrance, influencing reactivity and selectivity in coupling reactions, while the chlorine atom provides a reactive site for further functionalization. Its stable structure and well-defined reactivity make it valuable for constructing complex heterocyclic frameworks. The compound is typically handled under standard laboratory conditions, with purity and consistency being critical for reproducible results in synthetic applications.
2-(Tert-Butyl)-6-chloropyridine structure
97691-23-1 structure
Product Name:2-(Tert-Butyl)-6-chloropyridine
CAS No:97691-23-1
MF:C9H12ClN
MW:169.651281356812
MDL:MFCD15526818
CID:1123470
PubChem ID:14570983
Update Time:2025-10-22

2-(Tert-Butyl)-6-chloropyridine Chemical and Physical Properties

Names and Identifiers

    • 2-chloro-6-(1,1-dimethylethyl)-Pyridine
    • 2-(tert-Butyl)-6-chloropyridine
    • 2-chloro-6-tert-butylpyridine
    • 2-TERT-BUTYL-6-CHLOROPYRIDINE
    • FCH1145272
    • AX8270609
    • AS-63948
    • 97691-23-1
    • N11822
    • SCHEMBL179283
    • 2-(t-Butyl)-6-chloropyridine
    • AMY16362
    • MFCD15526818
    • AKOS023832390
    • DB-408478
    • 2-(Tert-Butyl)-6-chloropyridine
    • MDL: MFCD15526818
    • Inchi: 1S/C9H12ClN/c1-9(2,3)7-5-4-6-8(10)11-7/h4-6H,1-3H3
    • InChI Key: AMEALNUOZWKTJR-UHFFFAOYSA-N
    • SMILES: ClC1=CC=CC(C(C)(C)C)=N1

Computed Properties

  • Exact Mass: 169.0658271g/mol
  • Monoisotopic Mass: 169.0658271g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 128
  • 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: 3.5
  • Topological Polar Surface Area: 12.9

2-(Tert-Butyl)-6-chloropyridine Pricemore >>

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2-(Tert-Butyl)-6-chloropyridine Production Method

Production Method 1

Reaction Conditions
Reference
Alkylation of pyridine in free radical chain reactions utilizing alkylmercurials
Russell, Glen A.; et al, Journal of Organic Chemistry, 1985, 50(18), 3423-5

2-(Tert-Butyl)-6-chloropyridine Raw materials

2-(Tert-Butyl)-6-chloropyridine Preparation Products

Additional information on 2-(Tert-Butyl)-6-chloropyridine

Introduction to 2-(Tert-Butyl)-6-chloropyridine (CAS No. 97691-23-1)

2-(Tert-Butyl)-6-chloropyridine, with the chemical formula C11H13ClN, is a significant intermediate in modern pharmaceutical and agrochemical research. This compound, identified by its CAS number 97691-23-1, has garnered attention due to its versatile structural properties and potential applications in drug development. The presence of both a chloro substituent and a tert-butyl group makes it a valuable building block for synthesizing more complex molecules.

The tert-butyl group, characterized by its steric hindrance, plays a crucial role in modulating the reactivity and selectivity of the pyridine core. This feature is particularly useful in medicinal chemistry, where controlling the three-dimensional arrangement of atoms can influence binding affinity and metabolic stability. In contrast, the chloro substituent at the 6-position introduces electrophilic centers, facilitating further functionalization through nucleophilic aromatic substitution or cross-coupling reactions.

Recent advancements in synthetic methodologies have highlighted the utility of 2-(Tert-Butyl)-6-chloropyridine in constructing heterocyclic frameworks. For instance, studies have demonstrated its effectiveness in generating substituted pyridines, which are prevalent motifs in bioactive compounds. Researchers have leveraged its reactivity to develop novel derivatives with enhanced pharmacological properties. These derivatives exhibit promise in treating neurological disorders, infectious diseases, and cancer by targeting specific biological pathways.

In the realm of agrochemicals, 2-(Tert-Butyl)-6-chloropyridine has been explored as a precursor for herbicides and fungicides. Its structural features contribute to improved crop protection by interfering with essential enzymatic processes in pests. The integration of computational modeling has further refined the design of these agrochemicals, ensuring higher efficacy while minimizing environmental impact.

The synthesis of 2-(Tert-Butyl)-6-chloropyridine typically involves chlorination and alkylation reactions starting from pyridine derivatives. Modern synthetic routes emphasize atom economy and green chemistry principles, reducing waste and energy consumption. For example, catalytic methods employing palladium or copper complexes have been optimized to achieve high yields with minimal byproducts.

From a mechanistic perspective, the reactivity of 2-(Tert-Butyl)-6-chloropyridine has been extensively studied to understand its role in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. These transformations are pivotal in constructing biaryl systems, which are integral to many pharmaceuticals. The tert-butyl group’s steric bulk often directs these reactions toward specific regioisomers, enhancing synthetic control.

The pharmaceutical industry has shown particular interest in 2-(Tert-Butyl)-6-chloropyridine due to its role as a scaffold for kinase inhibitors. Kinases are critical targets in oncology, and modulating their activity can lead to therapeutic breakthroughs. Researchers have synthesized analogs of this compound that exhibit potent inhibitory effects on aberrant signaling pathways associated with cancer cell proliferation.

Additionally, 2-(Tert-Butyl)-6-chloropyridine has been investigated for its potential in developing antiviral agents. The pyridine core is a common structural element in drugs that disrupt viral replication cycles. By modifying the substituents on this core, scientists aim to create molecules that can selectively inhibit viral enzymes without affecting host cells.

The agrochemical sector has also benefited from the versatility of 2-(Tert-Butyl)-6-chloropyridine. Its derivatives have been incorporated into formulations that offer broad-spectrum pest control while adhering to stringent regulatory standards. The compound’s stability under various environmental conditions ensures prolonged activity, reducing the frequency of application required.

In conclusion, 2-(Tert-Butyl)-6-chloropyridine (CAS No. 97691-23-1) represents a cornerstone in synthetic chemistry with far-reaching implications across multiple industries. Its unique structural features enable diverse applications in pharmaceuticals and agrochemicals, driven by ongoing research into novel derivatives and reaction pathways. As scientific understanding evolves, this compound will likely continue to play a pivotal role in advancing chemical innovation.

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