Product Name	4-(Morpholinomethyl)aniline , 4-(Morpholinomethyl)aniline
CAS Number	51013-67-3
Molecular Formula	C₁₁H₁₆N₂O
Molecular Weight	192.26
SMILES Code	NC1=CC=C(CN2CCOCC2)C=C1
MDL No.	MFCD03659020
Pubchem ID	776851
InChI Key	WNYFVEFUHMDIRQ-UHFFFAOYSA-N

Synthesis route

Synthesis：51013-67-3

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6425-46-3		51013-67-3

Yield	Synthesis conditions	Experimental procedures
95%	With palladium on activated charcoal; hydrogen In methanol for 6 h;	11a (2.22 g, 10 mmol) was dissolved in methanol and, under nitrogen, 200 mg of Pd/C was added. The mixture was then reacted with H₂ for 6 hours. The filtrate was collected by filtration and concentrated to yield 1.83 g of a solid. Yield: 95%.
80.9%	With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate In ethanol at 65 - 78℃; for 5 h;	General procedure: A mixture of compounds 5a-e (0.05 mol) in ethanol was heated to 65°C. FeCl₃·6H₂O (2.8 g, 0.001 mol), activated carbon (0.18 g, 0.015 mol), and 80% hydrazine hydrate were added. (25 g, 0.5 mol) was added dropwise at a rate to maintain the temperature below 70°C. The reaction was heated under reflux for 5 hours, then cooled to room temperature and concentrated. Water (100 mL) was added, and the reaction solution was extracted three times with DCM. The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated to yield compounds 6a-e.
80.9%	With iron(III) chloride hexahydrate; hydrazine hydrate In ethanol for 5 h;	General Procedure: A mixture of compound 5 or 7a-c (0.05 mol) in ethanol was heated to 65°C. FeCl₃·6H₂O (2.8 g, 1 mmol) and activated carbon (0.18 g, 15 mmol) were added, and 80% hydrazine hydrate (25 g, 0.5 mol) was added dropwise at this temperature, maintaining the temperature below 70°C. The reaction was heated under reflux for 5 hours, then cooled to room temperature and concentrated. Water (100 mL) was added, and the reaction solution was extracted three times with CH₂Cl₂ (60 mL). The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated to afford compounds 8a-d.

Chemical Properties

This aniline derivative is a white to off-white crystalline solid melting at 95-97°C,with a predicted boiling point of 320.7°C.Its predicted density is 1.136 g/cm³.It should be stored in a dark place under an inert atmosphere at room temperature.It is slightly soluble in water but readily soluble in methanol,ethanol,THF,DMF,and has some solubility in ethyl acetate.The compound is stable under dry conditions.The morpholine nitrogen is weakly basic,and the aniline is moderately basic and nucleophilic,requiring protection from strong electrophiles and oxidizing agents if the free amine is to be preserved.

Description

4-(Morpholin-4-ylmethyl)aniline is a bifunctional molecule combining a primary aromatic amine with a tertiary aliphatic amine(morpholine)via a methylene linker.This structure provides two distinct nitrogen sites with different chemical environments and pKa values.The aniline allows for diazotization,amide formation,and participation in electrophilic aromatic substitution,while the morpholine offers water solubility,metal-chelating potential(via its oxygen),and the ability to form quaternary ammonium salts.It is a versatile polar linker and solubilizing group precursor.

Uses

1.Pharmaceutical Synthesis
Commonly used as a solubility-enhancing and pharmacokinetic-modifying fragment in drug design.It is incorporated into drug candidates to improve aqueous solubility and modulate logP/D.The aniline is often used to form anilide bonds with carboxylic acids of lead compounds,appending the morpholine tail.It is prevalent in the synthesis of protein kinase inhibitors,antibacterial quinolones,and serotonin receptor modulators.

2.Agrochemical R&D
Used to introduce basic nitrogen and polarity into agrochemical candidates,which can influence systemic movement(phloem mobility)in plants.The morpholine moiety can also interact with fungal or insect enzyme targets.It serves as a building block for certain systemic fungicides and insecticides where improved rainfastness and distribution within the plant are desired.

3.Functional Material Synthesis
Acts as a monomer or chain extender in the synthesis of polyurethanes,polyureas,and epoxy resins,where it contributes rigidity from the aromatic ring and crosslinking potential from the amines.It can also be used to functionalize carbon nanotubes or graphene oxide via diazonium chemistry,introducing morpholine groups to alter dispersion properties in composite materials.

4.Organic Synthesis Building Block
A standard reagent for preparing Schiff bases and imines via the aniline group.The resulting imines can be used in Strecker amino acid synthesis or reduction to secondary amines.It is also a precursor to azo dyes when diazotized and coupled with phenols or other aromatic amines,finding use in dyestuff chemistry.

4-(Morpholinomethyl)aniline , 4-(Morpholinomethyl)aniline

Synthesis route

Chemical Properties

Description

Uses