1,1,1-Trifluoromethanesulfonic acid 2-methylbenzofuro[2,3-b]pyridin-8-yl ester
[CAS# 1609373-98-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 1,1,1-Trifluoromethanesulfonic acid 2-methylbenzofuro[2,3-b]pyridin-8-yl ester
• Synonyms: (2-methyl-[1]benzofuro[2,3-b]pyridin-8-yl) trifluoromethanesulfonate
• Molecular Formula: C₁₃H₈F₃NO₄S
• Molecular Weight: 331.27
• CAS Registry Number: 1609373-98-9
• SMILES: CC1=NC2=C(C=C1)C3=C(O2)C(=CC=C3)OS(=O)(=O)C(F)(F)F

Properties

• Solubility: Insoluble (3.6E^-3 g/L) (25 ºC), Calc.^*
• Density: 1.567±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.6, Calc.^*
• Boiling Point: 412.0±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 202.9±28.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H302-H318
• Precautionary Statements: P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501

Discovory and Applicatios

1,1,1-Trifluoromethanesulfonic acid 2-methylbenzofuro[2,3-b]pyridin-8-yl ester is a complex chemical compound that contains functional groups typical of sulfonic acid esters and heterocyclic aromatic structures. It is part of a class of compounds featuring the trifluoromethanesulfonic acid (triflic acid) group, which is well-known for its strong acidity and high reactivity, particularly in organic synthesis and catalysis.

The compound is generally synthesized by reacting the appropriate 2-methylbenzofuro[2,3-b]pyridine derivative with 1,1,1-trifluoromethanesulfonic acid or its derivatives. The triflic acid group, characterized by its high electron-withdrawing nature, significantly enhances the reactivity of the molecule, particularly in reactions involving electrophilic substitution or nucleophilic attack. This feature has made trifluoromethanesulfonate esters valuable in various synthetic organic chemistry applications.

While the detailed literature on this specific compound is more limited compared to more common compounds, the general characteristics of its constituent parts can be used to infer its applications. Trifluoromethanesulfonic acid esters are often utilized as reagents in organic synthesis, particularly for their ability to act as strong electrophiles. They are useful in reactions requiring acid catalysis, such as alkylation, acylation, and Friedel-Crafts type reactions, where they serve as catalysts or reactants to facilitate the formation of new chemical bonds.

Additionally, the presence of the heterocyclic 2-methylbenzofuro[2,3-b]pyridine group introduces potential for the compound to function as a ligand in coordination chemistry, particularly in catalysis and organometallic chemistry. The complex aromatic structure can participate in various interactions, including pi-stacking and coordination with metal centers, which may enhance the reactivity and selectivity of the compound in catalysis.

Due to the reactivity of the trifluoromethanesulfonic acid ester group, such compounds can also be of interest in the development of materials or reagents for specific applications, such as those requiring stable but reactive intermediates. Furthermore, the heterocyclic component suggests potential applications in medicinal chemistry, particularly in designing compounds with biological activity, though the exact therapeutic applications of this specific ester are not well-documented in the literature.

In summary, 1,1,1-Trifluoromethanesulfonic acid 2-methylbenzofuro[2,3-b]pyridin-8-yl ester is primarily relevant as a chemical intermediate in organic synthesis, where it benefits from the strong reactivity of the trifluoromethanesulfonic acid ester group and the potential catalytic or coordination properties conferred by its heterocyclic structure. Further research into this specific compound and similar derivatives may reveal additional applications, especially in advanced organic synthesis, catalysis, and possibly medicinal chemistry.