63517-33-9 | Xtalfluor-M

CAS:63517-33-9 | Xtalfluor-M ,Description

Xtalfluor-M is a new type of fluorophore developed as a tool for cell imaging and analysis. It is a water-soluble and non-toxic fluorescent dye which can be used to detect and visualize a variety of biomolecules and cellular structures. It is a versatile fluorophore that has a wide range of applications in cell biology, molecular biology and biochemistry.
 

Scientific Research Applications

Enhanced Thermal Stability and Handling

Xtalfluor-M, a morpholinodifluorosulfinium tetrafluoroborate, is recognized for its enhanced thermal stability and ease of handling compared to its analogues like Deoxo-Fluor and DAST. It offers safer and more cost-efficient preparation, avoiding hazardous distillation processes. Notably, Xtalfluor reagents do not generate corrosive free-HF, enabling their use in standard borosilicate vessels. They are effective in converting alcohols to alkyl fluorides and carbonyls to gem-difluorides, exhibiting greater selectivity and reduced side products than similar reagents (L’Heureux et al., 2010) .

Diverse Organic Transformations

Xtalfluor-E, closely related to Xtalfluor-M, demonstrates wide applicability in various chemical transformations beyond deoxyfluorination. It's used in dehydration, cyclodehydration, ring expansion, formylation, and proto-functionalization. This review highlights the diverse roles of Xtalfluor-E in organic synthesis, underscoring its versatility and importance beyond being a deoxofluorinating agent (Mohammadkhani & Heravi, 2019).

Catalytic Proto-functionalization

Xtalfluor-E® is extensively used for catalytic proto-functionalization of activated olefins. This involves generating protons in situ with protic nucleophiles, leading to proto etherification of enamides to form N,O-acetals in nearly quantitative yields. This illustrates its potential in specific organic synthetic pathways (Yi et al., 2017) .

Vilsmeier-Haack Formylation

Xtalfluor-E has been used as an alternative to POCl3 in the Vilsmeier-Haack formylation reaction of C-2-glycals. This method achieved C-2-formyl glycals in varying yields and was extended to the synthesis of a C-2-formylated disaccharide glycal. This application provides an efficient pathway for formylation, essential in various synthetic chemistry applications (Roudias et al., 2018).

Synthesis of Isocyanides and Nitriles

Xtalfluor-E facilitates the formation of isocyanides from formamides and nitriles from aldoximes and amides. It allows for rapid, room temperature reactions in an environmentally benign solvent with only a slight excess of the dehydrating agent. This method's broad scope, including the preparation of chiral nonracemic nitriles, highlights its efficiency and environmental friendliness in organic synthesis (Keita et al., 2015).

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