4-Benzyl-2-(chloromethyl)morpholine: Properties & Lab FAQ

4-Benzyl-2-(chloromethyl)morpholine is a morpholine-based heterocyclic building block bearing both a reactive chloromethyl electrophilic handle and an N-benzyl protecting group, making it a versatile intermediate in organic and medicinal chemistry synthesis.

Product SKU

B701332

Chemical Name

4-Benzyl-2-(chloromethyl)morpholine

Core Scaffold

Morpholine (six-membered ring containing N and O)

Key Functional Groups

Chloromethyl (electrophile), N-benzyl (protecting group)

Primary Use

Synthetic intermediate and building block in organic/medicinal chemistry

Supplier

Aladdin Scientific

What Is 4-Benzyl-2-(chloromethyl)morpholine?

4-Benzyl-2-(chloromethyl)morpholine (SKU: B701332) is a morpholine derivative in which the nitrogen atom carries a benzyl protecting group and the 2-position of the ring bears a chloromethyl substituent. The morpholine scaffold — a saturated six-membered heterocycle containing both a nitrogen and an oxygen atom — is widely encountered in pharmaceutical and agrochemical research owing to its favorable aqueous solubility, moderate basicity, and metabolic stability. The chloromethyl group serves as an electrophilic handle for nucleophilic substitution reactions, enabling the attachment of diverse nucleophiles to build more complex molecular architectures. The N-benzyl group both protects the ring nitrogen and can be removed by catalytic hydrogenolysis when a free secondary amine is required in subsequent steps.

Handling, Storage, and Safety

As with all chloromethyl-containing compounds, 4-Benzyl-2-(chloromethyl)morpholine should be treated as a potential alkylating agent and handled with appropriate precautions. Work should be conducted in a well-ventilated fume hood, and personnel should wear suitable personal protective equipment including nitrile gloves, safety glasses, and a laboratory coat. The compound should be stored in a cool, dry location away from moisture, strong bases, and oxidising agents, and tightly sealed to prevent hydrolysis of the reactive C–Cl bond. Spills should be neutralised and disposed of according to local regulations for halogenated organic compounds. Always consult the Safety Data Sheet (SDS) provided with the product before use.

Note: Specific physical properties such as melting point, boiling point, and flash point are not confirmed in the current source material and should be verified in the SDS or primary literature before use.

Applications in Synthesis

The dual functionality of 4-Benzyl-2-(chloromethyl)morpholine makes it attractive for multi-step synthesis. The chloromethyl group can react with a broad range of nucleophiles — including amines, thiols, azides, malonate anions, and phenols — via S_N2 displacement to introduce new carbon–heteroatom bonds with retention or inversion of stereochemistry depending on reaction conditions. Once the desired transformations have been performed at the chloromethyl terminus, the N-benzyl group can be removed by palladium-catalysed hydrogenolysis (H₂, Pd/C) to unmask the secondary morpholine nitrogen for further elaboration such as acylation, sulfonylation, reductive amination, or coupling with additional electrophiles. This protecting-group strategy makes the compound valuable for the preparation of morpholine-containing drug candidates and bioactive scaffolds.

Ordering and Availability from Aladdin Scientific

4-Benzyl-2-(chloromethyl)morpholine is available from Aladdin Scientific under SKU B701332. To place an order, visit the Aladdin Scientific website, search by product name or SKU, and add the desired quantity to your cart. For bulk quantities, custom packaging, or institutional pricing, please contact the Aladdin Scientific sales team directly. Lead times, available pack sizes, and current stock levels can be confirmed through the product page or by contacting customer service. All products are dispatched with a certificate of analysis (CoA) and Safety Data Sheet (SDS).

Frequently asked questions

What is the CAS number for 4-Benzyl-2-(chloromethyl)morpholine?

The CAS number for 4-Benzyl-2-(chloromethyl)morpholine is not confirmed in the current source material provided. Please refer to the product page for SKU B701332 on the Aladdin Scientific website or consult the certificate of analysis for the verified CAS number.

How should I store 4-Benzyl-2-(chloromethyl)morpholine to maintain its stability?

The compound should be stored in a tightly sealed container in a cool, dry place, away from moisture, strong bases, and oxidising agents. These precautions minimise hydrolysis of the reactive chloromethyl group and prolong shelf life. Always consult the SDS for specific temperature and storage recommendations.

What nucleophiles can react with the chloromethyl group of this compound?

The chloromethyl group is an activated primary alkyl chloride that can undergo SΝ2 displacement with a wide range of nucleophiles, including primary and secondary amines, thiols, sodium azide, stabilised carbanions such as malonates, and oxygen nucleophiles such as phenoxides. The choice of nucleophile, solvent, base, and temperature will influence both yield and, where applicable, stereoselectivity.

How can the N-benzyl protecting group be removed after synthesis?

The N-benzyl group on the morpholine nitrogen can be cleaved by catalytic hydrogenolysis using hydrogen gas over a palladium on carbon (Pd/C) catalyst in a suitable solvent such as ethanol or methanol at atmospheric or slightly elevated pressure. This deprotection step reveals the free secondary amine, which can then be used in further synthetic transformations.

Is 4-Benzyl-2-(chloromethyl)morpholine available in enantiopure form?

The current product listing for B701332 does not specify whether the compound is supplied as a racemate or in enantiopure form. Please contact Aladdin Scientific customer service or review the current product page and certificate of analysis for stereochemical specifications before ordering.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford University Press: Oxford, 2012. (General reference for morpholine chemistry and protecting group strategies.)
2. Aladdin Scientific. Product Page: 4-Benzyl-2-(chloromethyl)morpholine, SKU B701332. (Accessed via Aladdin Scientific website.)

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