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Description
TCI D3492 is (−)-dibenzoyl-L-tartaric acid, one of the most classical and most frequently used chiral resolving agents in organic chemistry. The compound is L-tartaric acid in which both hydroxyl groups have been esterified with benzoyl groups, giving a molecule that carries two stereogenic centres together with two free carboxylic acid functions. In the laboratory, its role is to form salts with racemic basic compounds, particularly amines, so that a mixture of enantiomers that cannot be separated directly is converted into a mixture of diastereomers with different solubilities that can be separated by crystallisation.
The property that makes this reagent the reagent of choice is the balance between a simple structure, a rigid chiral framework, and aromatic benzoyl groups large enough to direct the packing of the crystal lattice. The combination of hydrogen bonding from the carboxylic acid groups and aromatic interactions contributed by the benzoyl groups means that the diastereomeric salts formed often crystallise well in a wide range of solvent systems, including the alcohol–water mixtures that are easy to prepare in any laboratory. The reagent is also widely documented in the literature, so researchers can refer to a large body of established procedures.
In Indonesian laboratories, this reagent is used wherever a single enantiomer has to be obtained from a racemic base without recourse to specialised chromatographic equipment. Because the resolution is carried out with ordinary glassware, common solvents and simple crystallisation, it fits well into academic research groups, university teaching and research laboratories, and process development work in which reliable, well-referenced procedures are preferred over methods that require dedicated instrumentation.
Laboratory Applications
Classical resolution of racemic amines: the two free carboxylic acid groups form salts with basic nitrogen centres, converting inseparable enantiomers into diastereomers that differ in solubility.
Preparation of single-enantiomer chiral building blocks: the resolved amine or base recovered from the diastereomeric salt can be carried directly into asymmetric synthesis as a defined stereochemical starting point.
Diastereomeric salt crystallisation studies: the rigid tartrate backbone and aromatic benzoyl groups promote well-formed crystals, making the reagent suitable for screening solvent systems and crystallisation conditions.
Reproduction of established literature procedures: because the reagent appears extensively in the published literature, researchers can follow documented resolution protocols rather than developing conditions from scratch.
Teaching and demonstration of stereochemistry: the resolution can be performed with standard glassware and common alcohol–water solvent mixtures, which makes it a practical exercise for illustrating enantiomer separation.
Specifications
Brand: TCI (Tokyo Chemical Industry)
CAS number: 2743-38-6
Category: Chemistry > Asymmetric Synthesis > Chiral Building Blocks
Chemical identity: (−)-dibenzoyl-L-tartaric acid, the dibenzoate ester of L-tartaric acid bearing two free carboxylic acid groups
Pack sizes: available in the standard TCI catalogue pack sizes; please confirm the required pack size when ordering
Storage: keep in a tightly closed original container in a cool, dry place, away from moisture
Handling and Storage
Store the material in its tightly closed original container in a cool, dry and well-ventilated place, protected from moisture and kept away from strong bases and other incompatible reagents. Amber glass or the supplier's original packaging is suitable; transfer only the quantity required for the experiment and reseal the container promptly to avoid moisture uptake. As with any organic acid, handle the solid in a fume hood or well-ventilated area and wear safety glasses, gloves and a laboratory coat, since the compound may irritate skin, eyes and the respiratory tract. Avoid generating dust during weighing, clean spills immediately, and dispose of residues and contaminated materials in accordance with the applicable chemical waste procedures of the laboratory. Always consult the manufacturer's safety data sheet before use.
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