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Description
TCI D3507 Diethyl Pyrazole-3,5-dicarboxylate is a heterocyclic building block consisting of a pyrazole ring carrying two ethyl ester groups at the 3 and 5 positions. Pyrazole is one of the most frequently encountered heterocyclic cores in pharmaceutical compounds and agrochemical materials, which means that a starting material already containing this ring with functional groups in place saves a considerable amount of laboratory working time. The role of this compound is to provide a symmetrical pyrazole framework that is ready for modification, either at the ring nitrogen atom or at both ester groups, in order to construct more elaborate molecules.
The properties that make this compound a preferred choice are its symmetry and the diversity of its reaction points. Both ester groups can be hydrolysed to the corresponding acids, converted into amides, reduced to alcohols, or processed stepwise to give mono-acid derivatives that are useful as linkers. The pyrazole nitrogen atom is weakly acidic and can be alkylated or arylated to produce N-substituted derivatives, although the possible formation of regioisomeric mixtures should be kept in mind for unsymmetrical pyrazoles. The structure is also recognised as a source of chelating groups, owing to the combination of the ring nitrogen and the adjacent carbonyl functionality.
In Indonesian laboratories, this type of heterocyclic building block is typically used in synthetic organic chemistry research at universities and research institutes, as well as in the development laboratories of pharmaceutical and agrochemical companies. Because the pyrazole ring is already assembled and functionalised, work can begin directly at the derivatisation stage rather than with construction of the core, which is particularly valuable where synthetic route length and reagent availability are limiting factors.
Laboratory Applications
Synthesis of pharmaceutical intermediates: the pyrazole core is common in drug molecules, and the two ester groups provide immediate handles for building more complex target structures.
Preparation of agrochemical candidate compounds: pyrazole is a frequently used core in agrochemical materials, so a pre-functionalised ring shortens the synthetic route to new derivatives.
Amide and carboxylic acid library synthesis: both esters can be hydrolysed to acids or converted into amides, allowing systematic variation of substituents around one common scaffold.
Mono-functionalised linker preparation: stepwise treatment of the symmetrical diester gives mono-acid derivatives that serve as connecting units between two molecular fragments.
Coordination and ligand chemistry studies: the combination of ring nitrogen atoms and adjacent carbonyl groups makes this structure useful as a source of chelating groups for metal complexes.
Specifications
Brand: TCI
CAS number: 37687-24-4
Chemical name: Diethyl Pyrazole-3,5-dicarboxylate
Catalogue code: D3507
Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
Storage: store in a closed original container in a cool, dry place; refer to the manufacturer's label and safety data sheet for the specific conditions of the pack supplied
Handling and Storage
Store the material in its tightly closed original container, in a cool, dry and well-ventilated area away from direct sunlight, moisture, heat sources and incompatible chemicals. Ester functional groups are sensitive to prolonged exposure to moisture, so the container should be reclosed immediately after each use and weighing carried out quickly. Handle the compound in a fume hood or a well-ventilated working area, wearing safety glasses, gloves and a laboratory coat, and avoid contact with skin and eyes as well as inhalation of dust. Use clean, dry glassware or a spatula when transferring material to prevent cross-contamination, keep the original label legible, and always consult the manufacturer's safety data sheet before use and for waste disposal.
