(2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine: Key FAQs

(2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine is a chiral morpholine-based building block bearing a reactive chloromethyl handle and an N-benzyl protecting group, widely employed as an enantiopure intermediate in asymmetric synthesis and pharmaceutical research.

Chemical Name

(2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine

SKU / Catalog Number

M698924

Molecular Formula

C12H16ClNO

Molecular Weight

225.71 g/mol

Stereochemistry

Single enantiomer, (R)-configuration at C-2

Key Functional Groups

Chloromethyl (electrophilic alkylating handle), N-benzyl (removable protecting group), morpholine ring (N,O-heterocycle)

Overview and Chemical Identity

(2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine (Aladdin SKU: M698924) is an enantiopure heterocyclic compound belonging to the morpholine family. Its structure combines three key features: a six-membered morpholine ring providing a conformationally defined scaffold, a chloromethyl group at the C-2 position serving as a versatile electrophilic handle for nucleophilic substitution reactions, and an N-benzyl group that both protects the ring nitrogen and can be removed via hydrogenolysis when a free secondary amine is required downstream.

The molecular formula is C₁₂H₁₆ClNO with a molecular weight of approximately 225.71 g/mol. The defined (R)-stereocentre at C-2 makes this compound suitable for applications where chirality transfer is essential.

Applications in Synthesis

This compound serves primarily as a chiral building block and pharmaceutical intermediate. The chloromethyl group undergoes facile S_N2 reactions with diverse nucleophiles—including amines, thiols, azides, and carbon nucleophiles—enabling efficient introduction of the chiral morpholine motif into target molecules. Because the morpholine ring is a privileged scaffold in medicinal chemistry, this reagent is particularly valuable for constructing drug candidates and bioactive natural product analogues.

The N-benzyl protecting group offers orthogonal deprotection: hydrogenolysis under standard Pd/C–H₂ conditions cleanly removes the benzyl group to reveal the free amine, expanding the synthetic utility of the compound. Researchers engaged in asymmetric total synthesis, fragment-based drug discovery, and preparation of chiral ligands or auxiliaries are the primary end users.

Handling, Storage, and Safety

As an alkyl chloride, (2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine is a reactive electrophile and should be handled with appropriate precautions. Work in a well-ventilated fume hood, wear nitrile gloves, safety glasses, and a lab coat. Avoid prolonged skin or eye contact. Consult the product's Safety Data Sheet (SDS) prior to use for full hazard classification, first-aid measures, and disposal guidance.

For storage, keep the compound in a tightly sealed container under inert atmosphere (argon or nitrogen) at 2–8 °C or as specified on the product label, away from moisture, heat, and incompatible bases or strong nucleophiles that could trigger premature reaction. Under recommended conditions, the compound is expected to be stable for an extended period; verify the retest date printed on the label before use.

Purity, Specifications, and Quality

Aladdin Scientific supplies (2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine under catalog number M698924. Specific purity grades, analytical data (such as HPLC purity, optical rotation, NMR spectra, and enantiomeric excess), and available pack sizes are detailed on the product page. Customers requiring a Certificate of Analysis (CoA) or copies of analytical data for a specific lot number may contact Aladdin's technical support team.

When evaluating this reagent for sensitive asymmetric transformations, confirm the enantiomeric excess (ee) value reported for the supplied lot, as high ee is critical for predictable stereochemical outcomes. For regulatory or GMP-adjacent workflows, inquire about documentation availability when placing your order.

Ordering and Availability

(2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine is available for order from Aladdin Scientific under SKU M698924. To place an order, visit the Aladdin Scientific website, search by catalog number or product name, select the desired quantity, and proceed to checkout. Bulk or custom quantities may be available upon request — contact our sales team for pricing and lead-time information.

For procurement teams, Aladdin offers institutional accounts, purchase order (PO) processing, and volume pricing. If you need this compound as part of a larger project requiring multiple chiral building blocks, our technical team can assist with compound selection and sourcing.

Frequently asked questions

What is (2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine used for?

It is used primarily as a chiral building block and pharmaceutical intermediate. The reactive chloromethyl group allows nucleophilic substitution with amines, thiols, azides, and carbon nucleophiles, introducing the enantiopure morpholine scaffold into target molecules for asymmetric synthesis and drug discovery applications.

How should I store (2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine to maintain its stability?

Store the compound in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C or as specified on the product label. Keep it away from moisture, heat, and strong nucleophiles. Always verify the retest date on the label before use to confirm that the material is within its validity period.

Can the N-benzyl group be removed after synthesis?

Yes. The N-benzyl group is a standard removable protecting group. It can be cleanly cleaved by catalytic hydrogenolysis, typically using Pd/C under a hydrogen atmosphere, to reveal the free secondary amine. This orthogonal deprotection strategy makes the compound highly versatile for multi-step synthesis.

What purity and analytical data are available for M698924?

Specific purity levels, HPLC data, optical rotation, NMR spectra, and enantiomeric excess values for each lot are listed on the Aladdin Scientific product page. A Certificate of Analysis (CoA) for a specific batch can be requested from the technical support team.

How do I order (2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine from Aladdin Scientific?

Search for catalog number M698924 on the Aladdin Scientific website, select your required pack size, and add to cart. For bulk quantities, custom packaging, or institutional purchase orders, contact the Aladdin sales team directly for pricing and availability.

What safety precautions should I take when handling this compound?

Handle in a well-ventilated fume hood wearing nitrile gloves, safety glasses, and a lab coat, as the chloromethyl group makes this compound a reactive alkylating agent. Consult the Safety Data Sheet (SDS) for full hazard information, first-aid guidance, and waste disposal requirements before beginning any experiment.

References

1. Aladdin Scientific product page: (2R)-2-(Chloromethyl)-4-(phenylmethyl)morpholine, SKU M698924.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for Sₙ₂ reactions and protecting group chemistry.)
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. (Reference for benzyl deprotection via hydrogenolysis and morpholine scaffold chemistry.)

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