4-Morpholinoaniline Chemical Properties

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.

pka

6.72±0.40(Predicted)

form 

Crystalline Powder

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

4-(4-Morpholino)aniline (2524-67-6)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-36/37/39-22

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Morpholinoaniline Usage And Synthesis

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

4-Morpholinoaniline(2524-67-6)Related Product Information

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