4-Morpholinoaniline

Base Information

• Chemical Name: 4-Morpholinoaniline
• CAS No.: 2524-67-6
• Deprecated CAS: 131852-32-9
• Molecular Formula: C10H14N2O
• Molecular Weight: 178.234
• Hs Code.: 29349990
• European Community (EC) Number: 219-760-1
• NSC Number: 26334
• UNII: 6DRK9JS9QD
• DSSTox Substance ID: DTXSID8062490
• Nikkaji Number: J39.631A
• Wikidata: Q72492919
• Mol file: 2524-67-6.mol

Synonyms:4-Morpholinoaniline;2524-67-6;4-morpholinobenzenamine;4-morpholin-4-ylaniline;N-(4-Aminophenyl)morpholine;4-Morpholin-4-yl-phenylamine;p-Morpholinoaniline;4-(morpholin-4-yl)aniline;4-(4-Morpholino)aniline;Benzenamine, 4-(4-morpholinyl)-;4-Morpholinyl aniline;Morpholine, 4-(p-aminophenyl)-;4-morpholin-4-ylphenylamine;4-(4-aminophenyl)-morpholine;4-(4-Morpholinyl)aniline;86759-37-7;MFCD00006169;4-(4-Aminophenyl)morpholine;N-(4'-Aminophenyl)morpholine;4-morpholino aniline;4-morpholin-4-yl aniline;EINECS 219-760-1;NSC 26334;NSC-26334;4-morpholinophenylamine;4morpholinoaniline;NSC26334;4-morpholinylaniline;p-morpholino aniline;4-morpholin4-ylaniline;4-(morpholino)phenylamine;4-amino phenyl morpholine;6DRK9JS9QD;4-MORPHILINOANILINE;4-morpholin-4-yl-aniline;4-MORPHOLINOZNILINE;TimTec1_002302;4-(Morpholin4yl)phenylamine;Oprea1_542171;Oprea1_685520;SCHEMBL20631;4-(4-morpholinyl)benzenamine;4-(morpholin-4-yl)-aniline;4-(4-Morpholinyl)aniline #;N-(4-aminophenyl)-morpholine;4-Morpholinoaniline, >=98%;75655;(4-morpholin-4-ylphenyl)amine;F2107-0001;DTXSID8062490;PHNDZBFLOPIMSM-UHFFFAOYSA-;(4-morpholin-4-yl-phenyl)-amine;BCP13784;CS-B0267;CS-M0409;STR01950;[4-(morpholin-4-yl)-phenyl]-amine;STK038374;AKOS000100057;SB17801;SDCCGMLS-0065838.P001;10G-307S;SY002653;AM20061201;BB 0217174;FT-0629203;M1466;EN300-30034;VU0494694-1;A23754;D77205;A817738;W-206941;Z56899028

Chemical Property of 4-Morpholinoaniline

Chemical Property:

• Appearance/Colour: purple to brown crystalline powder
• Vapor Pressure: 1.31E-05mmHg at 25°C
• Melting Point: 132-135 °C(lit.)
• Refractive Index: 1.589
• Boiling Point: 368 °C at 760 mmHg
• PKA: 6.72±0.40(Predicted)
• Flash Point: 176.4 °C
• PSA: 38.49000
• Density: 1.149 g/cm³
• LogP: 1.75160
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Soluble in chloroform, ethyl acetate.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 178.110613074
• Heavy Atom Count: 13
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

4-Morpholinoaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1COCCN1C2=CC=C(C=C2)N
• Chemical Composition and Structure: 4-Morpholinoaniline, also known as 4-MA, is a compound composed of a morpholine ring attached to an aniline ring. Its chemical structure consists of an amino group attached to the benzene ring of aniline and a morpholine group attached to the same benzene ring.
• Uses: 4-Morpholinoaniline is used in organic synthesis reactions for the production of N-phenylquinoneimine derivatives and phthalocyanine compounds.^[1] It is also studied for its potential applications in photodynamic therapy (PDT) for cancer treatment.^[2]
• Mechanism of Action: The mechanism of action of 4-Morpholinoaniline varies depending on its application. In electrochemical processes, it undergoes oxidation to form quinone-diimine derivatives, which can further react with nucleophiles.^[3] In biological systems, such as DNA interaction studies, it may exhibit DNA cleavage activity and cytotoxic/phototoxic properties.
• Analysis Method: Analysis of 4-Morpholinoaniline and its derivatives can be performed using various spectroscopic techniques, such as Fourier Transform–Infrared (FT–IR) spectroscopy, Mass Spectra Analysis (MALDI–TOF–MS), and Nuclear Magnetic Resonance (NMR) spectroscopy. Additionally, its interaction with DNA and cytotoxic/phototoxic properties can be evaluated using assays such as agarose gel electrophoresis and MTT assay.
• References: [1] Green Electrochemical Synthesis of N-Phenylquinoneimine Derivatives: Dual Action of 4-Morpholinoaniline and N-(4-Aminophenyl) Acetamide; DOI 10.1021/acssuschemeng.7b02553; [2] DNA interaction and anticancer properties of new peripheral phthalocyanines carrying tosylated 4-morpholinoaniline units; DOI 10.1016/j.poly.2019.114319; [3] Mechanistic and Thermodynamic Study of Electrochemical Oxidation of 4-Morpholinoaniline in the Presence of Different Nucleophiles; DOI 10.1149/2.1441713jes

Technology Process of 4-Morpholinoaniline

There total 22 articles about 4-Morpholinoaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

→ 4-morpholino-4-yl-phenylamine (2524-67-6,86759-37-7)

Guidance literature:

Reference yield: 96.0%

morpholine (110-91-8,99108-56-2) + 4-chloro-aniline (106-47-8) → 4-morpholino-4-yl-phenylamine (2524-67-6,86759-37-7)

Guidance literature:

With ⁽⁵⁵⁾Pd₀₆₈⁽⁴⁴⁾Ni₀₃₂; potassium carbonate; In water; at 80 ℃; for 8h; Catalytic behavior;

DOI:10.1039/c4ra06958g

Reference yield: 91.0%

4-bromophenyl-morpholine (30483-75-1) → 4-morpholino-4-yl-phenylamine (2524-67-6,86759-37-7)

Guidance literature:

With copper(I) oxide; ammonium hydroxide; N¹-(furan-2-ylmethyl)-N²-(2-methylnaphthalen-1-yl)oxalamide; potassium hydroxide; In ethanol; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00901

upstream raw materials:

4-(4-nitroso-phenyl)-morpholine

1-morpholino-4-nitrobenzene

morpholine

4-bromo-aniline

Downstream raw materials:

N-furfurylidene-4-morpholino-aniline

acetoacetic acid-(4-morpholino-anilide)

2-[(4-Morpholino-phenylimino)-methyl]-phenol

N-(4-morpholinophenylcarbamothioyl)benzamide

Refernces

• 1、 -. "Synthesis method of linezolid intermediate". Paragraph 0043-0046. . Retrieved 2021/01/11.
• 2、 -. "2, 6, 8 - Polysubstituted imidazo [1, 2 - a] pyrazine and synthesis method and application thereof". . . Retrieved 2021/10/11.