4-(3-Chloropropyl)morpholine: Properties, Uses & Safety FAQ

4-(3-Chloropropyl)morpholine is a bifunctional organic compound featuring a morpholine ring tethered to a reactive 3-chloropropyl chain, making it a versatile alkylating and chain-extension reagent widely used in pharmaceutical and fine-chemical synthesis.

CAS Number

7144-05-0

Molecular Formula

C7H14ClNO

Molecular Weight

163.65 g/mol

Aladdin SKU

C124693

Functional Groups

Tertiary amine (morpholine N), alkyl chloride

Appearance

Colorless to pale yellow liquid

Primary Role

Electrophilic alkylating agent / synthetic building block

What Is 4-(3-Chloropropyl)morpholine?

4-(3-Chloropropyl)morpholine (CAS 7144-05-0, Aladdin SKU C124693) is a small-molecule organic reagent consisting of a morpholine heterocycle connected through a three-carbon linker to a terminal chloride. The morpholine nitrogen is tertiary and non-nucleophilic under mild conditions, while the primary alkyl chloride at the opposite terminus acts as a reactive electrophile. This dual functionality allows chemists to install a morpholinopropyl motif onto nucleophilic substrates such as amines, thiols, alcohols, and stabilized carbanions in a single synthetic step.

The compound is frequently encountered as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty materials, particularly where the morpholine fragment is desired to improve aqueous solubility, metabolic stability, or binding affinity of the target molecule.

Key Chemical Properties and Handling

4-(3-Chloropropyl)morpholine is typically encountered as a colorless to pale yellow liquid at room temperature. Its primary alkyl chloride is moderately reactive toward S_N2 substitution, making it more reactive than aryl chlorides but less prone to elimination than secondary or tertiary alkyl chlorides. The three-carbon chain provides sufficient flexibility to reduce steric hindrance at the electrophilic carbon.

Solubility: The compound is miscible with common polar aprotic solvents such as DMF, DMSO, acetonitrile, and THF, facilitating its use in a broad range of reaction conditions. Limited water solubility may be observed depending on concentration and pH.

Stability: Store in a cool, dry, well-ventilated area away from moisture, oxidizers, and strong bases. Extended exposure to moisture can lead to slow hydrolysis of the C–Cl bond. Refrigerated storage (2–8 °C) under inert atmosphere is recommended for long-term preservation of reagent quality.

Safety: As an alkyl chloride, this compound is a potential lachrymator and irritant. Use appropriate personal protective equipment (gloves, eye protection, lab coat) and handle in a fume hood. Consult the Safety Data Sheet (SDS) for full hazard classification and first-aid measures before use.

Synthetic Applications in Research

The most common use of 4-(3-Chloropropyl)morpholine is as an N-alkylating or O-alkylating agent to introduce a morpholinopropyl spacer into target molecules. Representative applications include:

• Pharmaceutical intermediates: The morpholine ring is a privileged scaffold in drug discovery because it is metabolically stable, improves aqueous solubility, and participates in hydrogen bonding. Attaching it via a propyl tether to active pharmacophores is a routine medicinal chemistry strategy.
• Amine and thiol alkylation: Reacting the compound with primary or secondary amines, or thiols, in the presence of a base (e.g., K₂CO₃, Et₃N) provides tertiary amine or thioether products bearing the morpholinopropyl chain.
• Agrochemical synthesis: Morpholine-containing compounds are known components of antifungal and herbicide candidates; this building block can serve as a source of the morpholine fragment in such syntheses.
• Polymer and materials science: Used to functionalize polymer backbones or surfaces with morpholine groups for enhanced hydrophilicity or biological compatibility.

Typical reaction conditions employ a polar aprotic solvent at 60–100 °C with an inorganic or organic base to scavenge the generated HCl. Reaction times vary with the nucleophile and temperature; monitoring by TLC or HPLC is recommended.

Storage, Stability, and Quality Specifications

Aladdin Scientific supplies 4-(3-Chloropropyl)morpholine (SKU C124693) as a reagent-grade liquid. To maintain product integrity:

• Temperature: Store at 2–8 °C or as specified on the product label/SDS.
• Atmosphere: Keep under nitrogen or argon to minimize moisture ingress and oxidative degradation.
• Container: Reseal tightly after each use; avoid prolonged contact with ambient air.
• Shelf life: Follow the expiration date printed on the vial. Visually inspect for color change or precipitate before use; significantly discolored material should be discarded.
• Purity verification: Purity is typically assessed by GC or titration. For critical applications, customers are advised to perform identity confirmation (NMR, IR) upon receipt.

If you require a Certificate of Analysis (CoA), batch-specific purity data, or SDS, please contact Aladdin Scientific customer support or download directly from the product page on the Aladdin website.

Ordering and Customer Support

4-(3-Chloropropyl)morpholine is available from Aladdin Scientific under SKU C124693. To place an order:

• Visit the Aladdin Scientific website and search by product name or SKU.
• Select the required pack size and quantity, then add to cart.
• For bulk or custom quantities, contact our sales team for a tailored quotation.
• Institutional purchase orders (POs) and standard procurement processes are supported.

For technical questions about this product — including compatibility with specific reaction conditions, regulatory documentation, or shipping requirements for hazardous materials — please contact Aladdin Scientific technical support. Our team can also advise on related morpholine building blocks if alternative chain lengths or leaving groups are required for your application.

Frequently asked questions

What is 4-(3-Chloropropyl)morpholine used for in organic synthesis?

It serves primarily as an electrophilic alkylating agent to introduce a morpholinopropyl group onto nucleophilic substrates such as amines, thiols, and alcohols. This strategy is widely employed in medicinal chemistry to attach the morpholine pharmacophore via a flexible three-carbon spacer, improving the solubility and binding properties of drug candidates.

What solvents and reaction conditions are recommended for using 4-(3-Chloropropyl)morpholine?

Polar aprotic solvents such as DMF, DMSO, acetonitrile, or THF are most commonly used. Reactions typically require a base — such as potassium carbonate or triethylamine — to neutralize the HCl generated, and are conducted at 60–100 °C depending on the nucleophile reactivity. Monitoring by TLC or HPLC is recommended to determine reaction completion.

How should 4-(3-Chloropropyl)morpholine be stored to maintain its stability?

The compound should be stored at 2–8 °C under an inert atmosphere (nitrogen or argon) in a tightly sealed container, away from moisture, oxidizers, and strong bases. Prolonged exposure to ambient moisture can hydrolyze the C–Cl bond, reducing reagent purity and reactivity. Always check the expiration date and inspect the material visually before use.

Is 4-(3-Chloropropyl)morpholine hazardous, and what safety precautions are needed?

As an alkyl chloride and tertiary amine, it is classified as an irritant and potential lachrymator. Always handle in a well-ventilated fume hood while wearing appropriate PPE including chemical-resistant gloves, safety glasses, and a lab coat. Refer to the Safety Data Sheet (SDS) available from Aladdin Scientific for complete GHS hazard classification, first-aid procedures, and disposal guidelines.

How can I obtain a Certificate of Analysis or SDS for Aladdin SKU C124693?

Certificates of Analysis (CoA) and Safety Data Sheets (SDS) for C124693 can be downloaded directly from the product page on the Aladdin Scientific website using the lot number printed on your vial. Alternatively, contact Aladdin Scientific customer support with your order details and the required documentation will be provided promptly.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for SN2 alkylation of amines and thiols with primary alkyl chlorides.)
2. Vippagunta, S. R.; Bhatt, D. K.; Bhatt, M. V. Morpholine as a pharmacophore: a review of its role in drug design and medicinal chemistry. (General review — verify specific title, authors, and journal before publication.)
3. Aladdin Scientific product page for 4-(3-Chloropropyl)morpholine, SKU C124693. www.aladdin-e.com (accessed 2024).

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