Benzyl L-(+)-Mandelate: Properties, Uses & FAQs

Benzyl L-(+)-Mandelate is a chiral ester of L-(+)-mandelic acid and benzyl alcohol, widely used as a building block and resolving agent in asymmetric synthesis and pharmaceutical research.

Product SKU

B136435

Chemical Name

Benzyl L-(+)-Mandelate

Molecular Formula

C₁₅H₁₄O₃

Molecular Weight

242.27 g/mol

Stereochemistry

L-(+) configuration; single enantiomer

Key Application

Chiral building block and resolving agent in asymmetric synthesis

What Is Benzyl L-(+)-Mandelate?

Benzyl L-(+)-Mandelate (SKU: B136435) is the benzyl ester of L-(+)-mandelic acid, a naturally occurring alpha-hydroxy acid with a well-defined stereocenter. The compound carries the L-(+) absolute configuration at the alpha-carbon bearing the hydroxyl group, making it a single enantiomer of defined optical purity. Its molecular formula is C₁₅H₁₄O₃ with a molecular weight of approximately 242.27 g/mol. The structure combines a phenyl-substituted chiral center with a benzyl ester protecting group, rendering it a versatile intermediate in synthetic organic chemistry.

Because it is derived from mandelic acid—one of the classical chiral pool starting materials—Benzyl L-(+)-Mandelate retains the predictable stereochemical outcome that researchers rely upon when designing enantioselective transformations.

Key Properties and Storage Conditions

Benzyl L-(+)-Mandelate is a white to off-white solid at room temperature. It is soluble in common organic solvents such as ethanol, methanol, dichloromethane, ethyl acetate, and dimethyl sulfoxide (DMSO). Solubility in water is low owing to its hydrophobic benzyl ester moiety. The optical rotation is positive [(+)] in appropriate solvents, consistent with the L-configuration of mandelic acid.

For long-term stability, the compound should be stored in a cool, dry, well-ventilated location away from light, heat, and moisture. A storage temperature of 2–8 °C or room temperature under inert conditions is generally recommended; consult the certificate of analysis (CoA) supplied with each lot for lot-specific guidance. Containers should be kept tightly sealed to prevent moisture uptake and decomposition of the ester bond.

Note: Always refer to the Safety Data Sheet (SDS) for handling precautions before use.

Research and Synthetic Applications

Benzyl L-(+)-Mandelate serves several important roles in research-grade organic synthesis:

• Chiral building block: The defined stereocentre at the alpha-carbon enables its use as a starting material for constructing complex chiral molecules with predictable absolute configuration.
• Optical resolution: Mandelic acid derivatives have a long history as resolving agents for racemic amines and acids. The benzyl ester form can be exploited in diastereomeric salt or ester resolution strategies.
• Protecting group chemistry: The benzyl ester is orthogonally deprotectable by hydrogenolysis (Pd/C, H₂) or Lewis acid conditions, providing flexibility in multi-step synthesis.
• Pharmaceutical intermediates: Enantiopure mandelate esters are relevant to the synthesis of active pharmaceutical ingredients (APIs) where stereochemical integrity is critical.
• Asymmetric catalysis studies: The compound can serve as a substrate or auxiliary in evaluating the performance of chiral catalysts or enzymes.

Researchers in medicinal chemistry, total synthesis, and process chemistry laboratories will find this reagent particularly useful where enantiopurity and functional-group versatility are both required.

Purity, Grade, and Quality Assurance

Aladdin Scientific supplies Benzyl L-(+)-Mandelate (B136435) as a research-grade reagent. Each production lot is accompanied by a Certificate of Analysis (CoA) detailing purity (typically assessed by HPLC or GC), optical rotation, appearance, and other relevant specifications. Researchers should download the current lot-specific CoA from the product page before use to confirm that the material meets their experimental requirements.

Enantiomeric excess (ee) is a critical quality parameter for chiral reagents. If your application is sensitive to ee, please contact Aladdin Scientific technical support to request ee data for the specific lot in question. For GMP or regulated environments, contact our sales team regarding documentation requirements.

Ordering, Availability, and Technical Support

Benzyl L-(+)-Mandelate is available from Aladdin Scientific under SKU B136435. To place an order, visit the product listing on the Aladdin Scientific website, select the desired quantity, and proceed through the standard checkout process. Bulk quantities and custom packaging may be available upon request—contact our sales team for pricing and lead times.

For technical inquiries—including solubility data, compatibility with specific reaction conditions, or custom synthesis questions—please reach out to Aladdin Scientific's technical support team via the contact form on our website or by email. Our team is available to assist research scientists, lab managers, and procurement specialists with reagent selection and application guidance.

Shipping is performed in accordance with applicable regulations for research chemicals. Please review the SDS for transport classification information before arranging shipment.

Frequently asked questions

What is the CAS number and molecular formula of Benzyl L-(+)-Mandelate?

Benzyl L-(+)-Mandelate has the molecular formula C₁₅H₁₄O₃ and a molecular weight of approximately 242.27 g/mol. For the confirmed CAS number, please refer to the product page for SKU B136435 on the Aladdin Scientific website, as CAS details are provided on the official product listing and Certificate of Analysis.

In which solvents is Benzyl L-(+)-Mandelate soluble?

Benzyl L-(+)-Mandelate is soluble in common organic solvents including ethanol, methanol, dichloromethane, ethyl acetate, and DMSO. Its solubility in water is low due to the hydrophobic benzyl ester group. For precise solubility data relevant to your application, contact Aladdin Scientific technical support.

How should Benzyl L-(+)-Mandelate be stored to maintain stability?

The compound should be stored in a cool, dry, well-ventilated area away from light, heat, and moisture, with containers kept tightly sealed. A temperature of 2–8 °C or room temperature under inert conditions is generally appropriate. Always consult the lot-specific Certificate of Analysis and Safety Data Sheet for precise storage instructions.

Can the benzyl ester group in Benzyl L-(+)-Mandelate be selectively removed?

Yes. The benzyl ester is deprotectable by catalytic hydrogenolysis using Pd/C under hydrogen atmosphere, a mild and well-established method in synthetic chemistry that leaves many other functional groups intact. Lewis acid conditions can also be applicable in certain contexts. The choice of deprotection conditions should be validated for each specific synthetic route.

What purity documentation is available for Benzyl L-(+)-Mandelate (B136435)?

Each lot of B136435 is supplied with a Certificate of Analysis (CoA) that includes purity data (typically by HPLC or GC), optical rotation, and appearance specifications. Lot-specific CoAs can be downloaded from the Aladdin Scientific product page. For enantiomeric excess data or additional quality documentation, please contact Aladdin Scientific technical support or your sales representative.

Is Benzyl L-(+)-Mandelate suitable for pharmaceutical intermediate synthesis?

Benzyl L-(+)-Mandelate is supplied as a research-grade reagent and is used as a chiral building block relevant to the synthesis of enantiopure pharmaceutical intermediates and active pharmaceutical ingredients. For GMP-grade material or regulated manufacturing applications, contact Aladdin Scientific's sales team to discuss documentation, grade availability, and compliance requirements.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for ester protecting group chemistry including benzyl esters.
2. Sheldon, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds. Marcel Dekker. Reference for mandelic acid as a chiral resolving agent.
3. Aladdin Scientific Product Page: Benzyl L-(+)-Mandelate, SKU B136435. https://www.aladdin-e.com

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.