| Identification | More | [Name]
4-Morpholinoaniline | [CAS]
2524-67-6 | [Synonyms]
4-(4-AMINOPHENYL)-MORPHOLINE
4-(4-MORPHOLINO)ANILINE
4-MORPHOLIN-4-YLANILINE
4-MORPHOLIN-4-YL-PHENYLAMINE
4-MORPHOLINOANILINE
4-MORPHOLINOPHENYLAMINE
AKOS B025582
AKOS BB-8569
AKOS BBS-00006991
ART-CHEM-BB B025582
ASISCHEM Z37706
LABOTEST-BB LT00083657
N-(4-AMINOPHENYL)MORPHOLINE
P-MORPHOLINOANILINE
4-(4-morpholinyl)-benzenamin
4-MORPHOLINOANILINE, 98+%
4-Morpholinoaniline or N-(4-Aminophenyl)morpholine
4-(4-MORPHOLINO)ANILINE, 98+%
4-MORPHOLIONOANILINE
4-morpholin-4-ylaniline hydrochloride | [EINECS(EC#)]
219-760-1 | [Molecular Formula]
C10H14N2O | [MDL Number]
MFCD00006169 | [Molecular Weight]
178.23 | [MOL File]
2524-67-6.mol |
| Chemical Properties | Back Directory | [Appearance]
PURPLE TO BROWN CRYSTALLINE POWDER | [Melting point ]
132-135 °C(lit.)
| [Boiling point ]
310.47°C (rough estimate) | [density ]
1.0777 (rough estimate) | [refractive index ]
1.5250 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Soluble in chloroform, ethyl acetate. | [form ]
Crystalline Powder | [pka]
6.72±0.40(Predicted) | [color ]
Purple to brown | [BRN ]
150957 | [InChI]
InChI=1S/C10H14N2O/c11-9-1-3-10(4-2-9)12-5-7-13-8-6-12/h1-4H,5-8,11H2 | [InChIKey]
PHNDZBFLOPIMSM-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=C(N2CCOCC2)C=C1 | [CAS DataBase Reference]
2524-67-6(CAS DataBase Reference) | [EPA Substance Registry System]
2524-67-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [RIDADR ]
UN2811 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
6.1 | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
PURPLE TO BROWN CRYSTALLINE POWDER | [Uses]
4-(4-Morpholinyl)aniline is used in the preparation of central nervous system (CNS) active agents, also used in the color developing process in photographs. | [Uses]
4-Morpholinoaniline is a morpholine derivative used in the preparation of central nervous system (CNS) active agents. 4-Morpholinoaniline is also one of the primary aromatic amines used in the colour
developing process in photographs. | [Synthesis]
The general procedure for the synthesis of 4-(4-morpholinyl)aniline from 4-(4-nitrophenyl)morpholine was as follows: referring to the method of Example 20, 4-(4-nitrophenyl)morpholine (10.3 g, 49.5 mmol; purchased from Lancaster Synthesis) was suspended in methanol (130 mL) and a methanolic solution of 2 M ammonia (70 mL). 1 mL of water and 5% palladium carbon catalyst (100 mg) were added. The mixture was placed in a Paar hydrogenation unit and hydrogenated at 50 psi hydrogen pressure for 1 hour. Upon completion of the reaction, the reaction mixture was allowed to cool to room temperature, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by solvent recrystallization from a mixture of ethyl acetate/hexane to give 4-(4-morpholinyl)aniline as a light purple solid (6.2 g, 70% yield, melting point 132-133 °C). The product was analyzed by GC/MS (EI, M+) and showed a molecular ion peak m/z=178. | [References]
[1] Applied Organometallic Chemistry, 2018, vol. 32, # 1,
[2] Chemistry - An Asian Journal, 2017, vol. 12, # 7, p. 785 - 791
[3] Patent: EP2949647, 2015, A1. Location in patent: Paragraph 0120
[4] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 896 - 905
[5] Patent: US2013/45977, 2013, A1. Location in patent: Paragraph 0215; 0216; 0217; 0218 |
|
|