Cas no 1243378-83-7 (5-tert-butoxy-2-chloro-pyridine)

5-tert-Butoxy-2-chloro-pyridine is a halogenated pyridine derivative featuring a tert-butoxy substituent at the 5-position and a chloro group at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The tert-butoxy group enhances steric and electronic properties, influencing reactivity and selectivity in cross-coupling reactions. The chloro substituent provides a reactive site for further functionalization, such as nucleophilic substitution or metal-catalyzed transformations. Its stable yet modifiable structure makes it valuable for constructing complex heterocyclic frameworks. The compound is typically handled under inert conditions due to its sensitivity to moisture and air. Suitable for research-scale and industrial applications requiring precise functional group manipulation.
5-tert-butoxy-2-chloro-pyridine structure
1243378-83-7 structure
Product Name:5-tert-butoxy-2-chloro-pyridine
CAS No:1243378-83-7
MF:C9H12ClNO
MW:185.650681495667
CID:4690899
Update Time:2025-05-19

5-tert-butoxy-2-chloro-pyridine Chemical and Physical Properties

Names and Identifiers

    • MB20018
    • 5-(TERT-BUTOXY)-2-CHLOROPYRIDINE
    • 5-tert-butoxy-2-chloro-pyridine
    • Inchi: 1S/C9H12ClNO/c1-9(2,3)12-7-4-5-8(10)11-6-7/h4-6H,1-3H3
    • InChI Key: KAHLUKPLTDCWGF-UHFFFAOYSA-N
    • SMILES: ClC1=CC=C(C=N1)OC(C)(C)C

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 144
  • XLogP3: 2.7
  • Topological Polar Surface Area: 22.1

5-tert-butoxy-2-chloro-pyridine Pricemore >>

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Additional information on 5-tert-butoxy-2-chloro-pyridine

Recent Advances in the Application of 5-tert-butoxy-2-chloro-pyridine (CAS: 1243378-83-7) in Chemical Biology and Pharmaceutical Research

The compound 5-tert-butoxy-2-chloro-pyridine (CAS: 1243378-83-7) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications as a key intermediate in the synthesis of bioactive molecules. This research brief aims to summarize the latest findings and developments related to this compound, highlighting its role in drug discovery and development.

Recent studies have demonstrated the utility of 5-tert-butoxy-2-chloro-pyridine as a building block in the synthesis of novel kinase inhibitors. A 2023 study published in the Journal of Medicinal Chemistry reported its use in the development of selective JAK2 inhibitors, which show promise for treating myeloproliferative disorders. The tert-butoxy group at the 5-position was found to enhance solubility while the chloro group at the 2-position facilitated further functionalization through cross-coupling reactions.

In pharmaceutical process chemistry, 1243378-83-7 has emerged as a critical intermediate in multi-step syntheses. A recent patent application (WO2023056123) describes its use in the kilogram-scale production of a novel antiviral candidate. The process optimization demonstrated that the compound's stability under various conditions makes it particularly suitable for large-scale manufacturing processes.

Structural-activity relationship (SAR) studies utilizing 5-tert-butoxy-2-chloro-pyridine have provided valuable insights into drug-target interactions. Research published in Bioorganic & Medicinal Chemistry Letters (2024) revealed that derivatives of this compound exhibit improved blood-brain barrier penetration compared to similar structures, suggesting potential applications in central nervous system drug development.

The compound's unique electronic properties have also been exploited in materials science applications. A 2024 study in ACS Applied Materials & Interfaces reported its use as a precursor for organic electronic materials, where the chlorine atom serves as a leaving group for subsequent functionalization while the tert-butoxy group provides steric bulk to control molecular packing.

From a safety and toxicology perspective, recent assessments indicate that 1243378-83-7 shows favorable preclinical safety profiles. The compound demonstrated low acute toxicity in rodent models (LD50 > 2000 mg/kg) and minimal genotoxic potential in standard assays, as reported in Regulatory Toxicology and Pharmacology (2023).

Future research directions appear to focus on expanding the utility of 5-tert-butoxy-2-chloro-pyridine in fragment-based drug discovery and as a versatile scaffold for combinatorial chemistry. Several ongoing clinical trials for cancer therapeutics list derivatives of this compound as key components, though specific structures remain proprietary at this stage.

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