(−)-Dibenzyl D-tartrate: Properties, Structure, and Practical Details

What is (−)-Dibenzyl D-tartrate?

(−)-Dibenzyl D-tartrate stands as a chiral organic compound built from the tartaric acid backbone. This substance holds significance in both academic and industrial chemistry, often found in organic synthesis labs for its resolving power in separating chiral compounds. The structure features a tartaric acid core where both carboxyl groups turn into benzyl esters, giving rise to a white to off-white crystalline solid. Its international trade and chemical identification fall under the HS Code 29181300, marking it as a tariff item in the classification of carboxylic acid derivatives.

Structural Insights and Molecular Formula

Delving into its structure, (−)-Dibenzyl D-tartrate possesses the formula C18H18O6, with a molar mass of 330.33 g/mol. Two phenyl rings attach to the D-tartrate skeleton via ester linkages, each side mirroring the other. The molecule’s optical activity comes from the D-tartrate core — a trait harnessed by chemists looking to separate racemic mixtures. Each crystal sparkles under polarized light because the material itself can rotate plane-polarized beams, a sign of its enantiomeric purity. These physical features make it stand out among tartaric acid esters, as the benzyl groups increase the molecule’s hydrophobicity and organic solubility.

Physical Characteristics: State, Density, Appearance

(−)-Dibenzyl D-tartrate usually comes as a crystalline solid, sometimes appearing in flakes or powder depending on how it crystallizes and is handled during manufacturing. Some suppliers offer the compound as fine pearls or larger granules, all sharing a consistent solid state at room temperature. Anyone weighing or transferring this material will notice it feels slippery and dense, with a measured density of about 1.23 g/cm3. The compound resists melting until reaching roughly 57-58°C, a useful feature for handling or purification steps. Its physical stability under normal conditions allows for safe transport and storage, provided moisture and direct sunlight do not come into play.

Chemical Properties and Use as Raw Material

This tartrate derivative reacts readily with hydrogenation catalysts, making it a prime choice when chemists aim to remove the benzyl protecting groups. As a building block, (−)-Dibenzyl D-tartrate serves in the creation of other tartaric compounds, pharmaceutical intermediates, and specialty materials that demand precise optical properties. Given its ester nature, it dissolves well in many organic solvents such as dichloromethane, chloroform, and toluene, but shows limited solubility in water. Its chemical stability and well-defined melting range are valued during multi-step synthesis, because each reaction step benefits from predictable, clean separations and straightforward purification.

Material Form, Solution Preparation, and Practical Handling

In solution form, (−)-Dibenzyl D-tartrate gives clear, colorless liquids when dissolved in standard laboratory solvents. This solubility feature lets researchers prepare precise concentrations per liter for various applications, ranging from chiral resolution to use as a synthetic intermediate. While working with this material in any lab setting, measuring its weight or volume becomes straightforward due to the crystalline nature, something not always possible with oils or viscous liquids. The solid serves as a stable reservoir for preparation, with any excess stored in airtight containers that hold up against air and humidity exposure.

Safety, Hazards, and Environmental Considerations

Chemical safety information for (−)-Dibenzyl D-tartrate often rates it as a low-hazard material, though handling practices always require gloves and eye protection. The primary hazard stems from possible irritation if the dust contacts skin or eyes, or if inhaled in significant amounts. Unlike volatile organic solvents, this solid stays put and does not vaporize easily, cutting down on inhalation risks. Disposal aligns with standard procedures for organic chemicals — collection in designated waste containers for later treatment. Anyone using it in larger-scale operations should ensure proper ventilation and containment to avoid accidental exposure or environmental release.

Why Purity and Traceability Matter

Consistent material quality drives successful chemical synthesis, so reputable suppliers of (−)-Dibenzyl D-tartrate provide full batch traceability, purity documentation, and analytical data verifying enantiomeric excess. Every percent point of impurity risks derailing downstream reactions, especially when making active pharmaceutical ingredients. The ability to check full molecular analysis before purchase helps chemists make informed choices. Throughout years of lab experience, it becomes clear that investing in a certified product streamlines workflow — fewer surprises during reactions, and greater reproducibility when scaling up.

Supporting Sustainable and Responsible Use

Growing awareness of environmental impact pushes chemists and raw material producers to source and manufacture (−)-Dibenzyl D-tartrate responsibly. Some suppliers now offer greener synthetic methods, minimizing hazardous reagent usage or recycling solvents. This aligns with industry push for sustainable chemistry, reducing unnecessary waste and solvent emissions. Every choice to purchase from a responsible source translates into a healthier work environment and reduced ecological footprint, making small steps toward bigger change in the chemical supply chain.