(2R,3R)-(-)-Dibenzoyl-L-tartaric acid anhydrous stands out in the world of chiral resolution agents. This compound, often recognized for its distinct capacity to resolve racemic mixtures, holds special popularity across both pharmaceutical and fine chemical landscapes. (2R,3R)-(-)-dibenzoyl-L-tartaric acid anhydrous takes its roots from natural tartaric acid, where two benzoyl groups have been added to adjust both solubility and selectivity in chemical reactions. The anhydrous form, free from water molecules, brings particular value when water-sensitive processing is a concern. Chemists lean on its reliability as a resolving agent for amines and other chiral bases, seeing solid performance where control of stereochemistry makes or breaks downstream product value.
This material comes as a crystalline solid—sometimes found in the form of fine powders but commonly prepared as glassy flakes or brittle, off-white shards depending on drying method and storage. As a solid, its handling feels similar to powdered sugar, yet it carries more heft thanks to a density hovering around 1.59 grams per cubic centimeter. Melting shows near 187–191 °C, pointing to purity and confirming that water hasn’t crept into the material during storage or shipping. In solution, the compound dissolves well in methanol and acetone, but stays less soluble in non-polar solvents like hexane. This split is practical: in a lab or plant, you rarely want surprises about where your material will dissolve or how well it’ll crystallize out.
The IUPAC name tells part of the story: (2R,3R)-2,3-Dihydroxybutanedioic acid dibenzoyl ester. Its unique structure, defined by the two benzoyl groups attached at the 2 and 3 positions of the tartaric acid backbone, gives it exceptional resolving power. The molecular formula reads as C18H14O7, clocking in at a molecular weight of approximately 342.3 g/mol. Stretching this molecule out in space, one sees its two rigid aromatic rings jutting away from a tartaric acid skeleton, conferring a decent degree of stereochemical bulk. Each chiral center, marked clearly as R in its systematic name, helps steer the formation of diastereomeric salts with amines and other bases—an essential function in separating mirror-image molecules, which can mean the difference between a medicine working or turning toxic.
Chemically sensitive projects want high purity, usually above 98%, with many suppliers testing every batch by chiral chromatography to ensure consistency. Materials ship in opaque, airtight drums or bottles that guard against ambient moisture, as contact with atmospheric water may trigger hydrolysis or spoil the resolving capacity. For laboratory-scale users, bottles of 25, 100, or 500 grams are common; in a larger process environment, 10-kilogram to 25-kilogram drums set the standard. The crystalline solid, when pulled from its container, offers no notable odor, and the fine particles flow much like commercial table salt. Quality control labs check not only chiral purity but look for common related substances, usually benzoyl derivatives, which sometimes sneak in during synthesis or storage.
Globally, (2R,3R)-(-)-dibenzoyl-L-tartaric acid anhydrous travels under HS Code 2918.19, falling into the family of carboxylic acids and their derivatives. Border authorities and shipping departments use this code to track import, export, and tariff obligations. Analytical labs routinely rely on this agent for enantioseparation, especially for resolving the nitrogen-containing bases that populate pharmaceutical intermediates. Contract manufacturing organizations (CMOs) include it in catalogues targeting specialty chemical and custom synthesis customers, especially for projects seeking control over absolute molecular configuration. Academic researchers, too, still turn to it for asymmetric synthesis trials or for prepping reference standards. My own run-ins with this material date to chiral chromatography projects, where the right salt formation depended on careful addition, tight storage, and plenty of patience to keep the anhydrous form pure.
(2R,3R)-(-)-dibenzoyl-L-tartaric acid anhydrous does not belong to the list of heavily hazardous chemicals. That doesn’t mean it deserves complacency. Standard good laboratory practices recommend gloves and goggles because the fine powder can irritate eyes and skin for sensitive individuals. Dust in the air creates only minor risk, but in larger quantities, inhalation may trigger coughing or sneezing. The material resists combustion but can release acrid, irritating fumes if subjected to open flame. Disposal follows the path of typical organic acids—dilution with copious water and neutralization with base prior to drain disposal, as advised for small-scale laboratory quantities. Environmental release in larger volumes could stress aquatic systems, but most regulatory bodies treat this agent as low hazard. Emergency showers and eye washes nearby suit the minimal risks, with proper clean-up to prevent slipping on spilled, dusty solids.
The compound lines up as an ester, requiring tartaric acid as its natural feedstock and benzoic acid or benzoyl chloride for the functional modification. Sourcing depends on a steady supply chain of both high-purity tartaric acid, often extracted from grape residues, and aromatic benzoyl derivatives. The chemical industry still leans heavily on European, Indian, and Chinese suppliers for base tartaric acid, while benzoic acid builds from petrochemical processes. Manufacturing plants overseen by key international chemical companies maintain ISO-certified conditions to produce food and pharmaceutical-grade tartaric acid derivatives. Verifiable supply records, traceability, and documentation assure customers that each batch meets the functional needs of GMP-regulated processes.
Complaints have surfaced over dust generation and the potential for low-level exposure to workers—issues best handled by enclosed handling systems, local exhaust ventilation, and proper training. The inherent chemical structure doesn’t introduce acute toxicity risks, but downstream synthesis waste streams sometimes require special attention, especially if the scale leans toward multi-kilogram outputs. Substitution with greener, less irritating alternatives rarely produces the same enantioselectivity, so process optimization means working closely with safety teams to develop clear protocols. Spill prevention, recycle opportunities, and continual review of environmental footprints round out best practices for handling—an approach that keeps workspaces both safe and responsible as production and laboratory use grow.
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