(S)-4-Benzyl-2-(hydroxymethyl)morpholine: Key FAQs

(S)-4-Benzyl-2-(hydroxymethyl)morpholine is a chiral, enantiopure morpholine derivative widely used as a versatile building block in asymmetric synthesis and pharmaceutical intermediate preparation.

CAS / SKU

B698918 (Aladdin SKU)

Chemical Class

Chiral morpholine derivative

Stereochemistry

(S)-configuration at C-2

Key Functional Groups

Tertiary amine (N-benzyl), morpholine ring oxygen, primary hydroxymethyl group

Primary Application

Asymmetric synthesis, chiral auxiliary, pharmaceutical intermediate

Storage Recommendation

Store in a cool, dry, well-ventilated area away from light and moisture

Overview and Chemical Identity

(S)-4-Benzyl-2-(hydroxymethyl)morpholine is an enantiopure, six-membered heterocyclic compound featuring both a nitrogen and an oxygen atom within the morpholine ring. The (S)-stereocenter at the C-2 position carries a hydroxymethyl (–CH₂OH) substituent, while the ring nitrogen bears an N-benzyl protecting group. This combination of a nucleophilic alcohol handle, a basic tertiary amine, and a defined stereocenter makes the compound a highly adaptable chiral building block.

The molecule is valued in medicinal chemistry and process chemistry because the morpholine scaffold frequently appears in bioactive compounds and approved drugs, and the pendant hydroxymethyl group can be selectively functionalized—oxidized to an aldehyde or acid, converted to a halide, or coupled via esterification and etherification reactions.

Handling, Storage and Safety

As with most amine-containing organic compounds, (S)-4-Benzyl-2-(hydroxymethyl)morpholine should be handled with appropriate personal protective equipment including laboratory gloves, safety goggles, and a lab coat. Operations generating dust or aerosols should be performed in a fume hood.

For storage, keep the compound in a tightly sealed container in a cool, dry, and well-ventilated location, protected from light and moisture. Prolonged or improper storage may lead to gradual degradation of optical purity or chemical integrity. Always consult the Safety Data Sheet (SDS) supplied with Aladdin product B698918 before use for up-to-date hazard classification and first-aid measures.

Note: Specific GHS hazard categories, flash point, and LD₅₀ values should be confirmed in the official SDS document, as these parameters are not reproduced here to avoid inaccuracy.

Applications in Synthesis

(S)-4-Benzyl-2-(hydroxymethyl)morpholine serves several roles in synthetic chemistry:

• Chiral building block: The defined (S)-stereocenter can be used to introduce chirality into target molecules via stereoretentive or stereodirected transformations.
• Chiral auxiliary precursor: After appropriate N-deprotection (hydrogenolytic removal of the benzyl group) or O-functionalization, the compound can be elaborated into more complex chiral auxiliaries or ligands.
• Pharmaceutical intermediate: The morpholine motif is prevalent in CNS drugs, kinase inhibitors, and antibacterials; this building block can serve as a scaffold for drug discovery libraries.
• Bifunctional linker: The simultaneous presence of an alcohol and an amine allows orthogonal protection and selective derivatization in multi-step synthesis.

Researchers are advised to confirm reaction conditions, yields, and selectivity data in primary literature before scaling up.

Purity, Quality and Analytical Specifications

Aladdin Scientific supplies (S)-4-Benzyl-2-(hydroxymethyl)morpholine (SKU: B698918) as a research-grade reagent. Key quality attributes typically assessed for chiral building blocks of this type include:

• Chemical purity: Determined by GC or HPLC; research-grade material typically targets ≥95% or higher—confirm the exact specification on the current Certificate of Analysis (CoA) available from Aladdin.
• Enantiomeric excess (ee): Critical for chiral reagents; verify the ee value on the CoA for each lot before use in stereoselective synthesis.
• Appearance: Typically a colorless to pale yellow liquid or solid depending on conditions—refer to the CoA for the current lot.
• NMR/MS identity confirmation: Identity is confirmed by spectroscopic methods; CoA data should be requested if not included with shipment.

For the most current and lot-specific specifications, request the CoA directly from Aladdin Scientific at the time of purchase.

Ordering and Customer Support

(S)-4-Benzyl-2-(hydroxymethyl)morpholine is available from Aladdin Scientific under SKU B698918. To place an order:

• Visit the Aladdin Scientific website and search for SKU B698918 or the full IUPAC name.
• Select the required pack size and quantity; bulk or custom quantities may be available upon request.
• For institutional purchase orders, blanket orders, or pricing inquiries, contact the Aladdin Scientific sales team directly.
• Certificates of Analysis, Safety Data Sheets, and technical documentation can be downloaded from the product page or requested from customer service.

For technical questions regarding synthesis applications, compatibility, or custom specifications, please contact Aladdin Scientific technical support. Return and refund policies follow Aladdin's standard terms—refer to the Help and Customer Service section of the website for details.

Frequently asked questions

What is (S)-4-Benzyl-2-(hydroxymethyl)morpholine used for?

It is primarily used as a chiral building block and pharmaceutical intermediate in asymmetric synthesis. The defined (S)-stereocenter, combined with the reactive hydroxymethyl group and the N-benzyl morpholine scaffold, allows it to be incorporated into complex molecules or further functionalized for drug discovery and process chemistry applications.

How should (S)-4-Benzyl-2-(hydroxymethyl)morpholine be stored?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, protected from light and moisture. Consult the Safety Data Sheet (SDS) provided with Aladdin product B698918 for the most precise and up-to-date storage conditions, including any recommended temperature range.

How do I confirm the enantiomeric purity of the material I receive?

Request the Certificate of Analysis (CoA) for the specific lot number of your order from Aladdin Scientific. The CoA will report the enantiomeric excess (ee) and other analytical data. If chiral HPLC verification in your own laboratory is required, Aladdin technical support can advise on suitable analytical methods.

Can the N-benzyl group be removed to give the free secondary amine?

Yes, N-benzyl groups are commonly removed by catalytic hydrogenolysis (e.g., Pd/C under H₂ atmosphere) under mild conditions, which typically leaves other functional groups such as the hydroxymethyl and morpholine oxygen intact. Researchers should verify specific conditions in primary literature before applying this transformation, as the presence of other sensitive groups may require protocol adjustments.

What analytical data are available for (S)-4-Benzyl-2-(hydroxymethyl)morpholine (B698918)?

Aladdin Scientific provides a Certificate of Analysis with each lot, which typically includes purity data (GC or HPLC), appearance, and identity confirmation by spectroscopic methods. For full spectral data such as ¹H NMR, ¹³C NMR, or MS spectra, please contact Aladdin customer service or visit the product page on the Aladdin website.

References

1. Aladdin Scientific product page for (S)-4-Benzyl-2-(hydroxymethyl)morpholine, SKU B698918. Certificate of Analysis and Safety Data Sheet available upon request.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for N-benzyl deprotection and morpholine chemistry.

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