4-(2-Aminoethyl)morpholine Chemical Properties

Melting point:

24 °C

Boiling point:

205 °C(lit.)

Density 

0.992 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.476(lit.)

Flash point:

347 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Chloroform, Methanol

form 

Liquid After Melting

pka

pK1: 4.06(+2);pK2: 9.15(+1) (25°C)

color 

Clear colorless to pale yellow

Water Solubility 

soluble

Sensitive 

Air Sensitive

BRN 

104378

Stability:

Air Sensitive

InChIKey

RWIVICVCHVMHMU-UHFFFAOYSA-N

CAS DataBase Reference

2038-03-1(CAS DataBase Reference)

NIST Chemistry Reference

4-Morpholineethanamine(2038-03-1)

EPA Substance Registry System

4-Morpholineethanamine (2038-03-1)

Safety Information

Hazard Codes 

C,T

Risk Statements 

22-34-43-24-40-23/24/25

Safety Statements 

26-36/37/39-45-22

RIDADR 

UN 2735 8/PG 2

WGK Germany 

2

RTECS 

QD7350000

Hazard Note 

Toxic

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29349990

Toxicity

guinea pig,LD50,skin,300uL/kg (0.3mL/kg),Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944.

MSDS

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

4-(2-Aminoethyl)morpholine Usage And Synthesis

Chemical Properties

clear colorless to pale yellow liq. after melting

Uses

4-(2-Aminoethyl)morpholine is used as a ligand and reacts with nickel(II) nitrite to form trans-bis[4-(2-aminoethyl)morpholine]dinitronickel(II).

Uses

4-(2-Aminoethyl)morpholine is widely used in biomedical applications as this moiety serves as an important lysosome-targeting group. Some of its applications include:

• Synthesis of the lysosome-targetable fluorescent probe for hydrogen sulfide imaging in living cells.
• Synthesis of 1,8-naphthalimide conjugated Troger′s bases as deoxyribonucleic acid (DNA) targeting fluorescent probe.
• Synthesis of intramolecular charge transfer-photoinduced electron transfer-fluorescence resonance energy transfer (ICT-PET-FRET) fluorescent probe for monitoring pH changes in living cells.
• It is also used as a precursor to synthesize a variety of antimicrobial agents.

Definition

ChEBI: 4-2-Aminoethyl-morpholine is a member of morpholines.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 34, p. 1805, 1991 DOI: 10.1021/jm00110a008

Synthesis

General procedure for the synthesis of N-(2-aminoethyl)morpholine from 2-morpholinoacetonitrile: LiAlH4 (3.19 g, 84 mmol) was added to anhydrous THF (35 mL) in a single step under ice bath conditions. The reaction mixture was stirred at 0 °C for 20 min, followed by the dropwise addition of 2-morpholino-substituted acetonitrile (3.50 g, 28 mmol) to a solution of anhydrous THF (10 mL). After the dropwise addition, the reaction mixture was heated to reflux for 3 hours. After completion of the reaction, the mixture was cooled to 0 °C and water (20 mL) was slowly added to quench the reaction. After filtration to remove insoluble material, the filtrate was concentrated in vacuum to give N-(2-aminoethyl)morpholine as a yellow oil (2.62 g, 72% yield).

References

[1] Patent: WO2014/12360, 2014, A1. Location in patent: Paragraph 00363
[2] Patent: US2015/87639, 2015, A1. Location in patent: Paragraph 0650
[3] Patent: TWI607995, 2017, B. Location in patent: Page/Page column 146
[4] Bulletin de la Societe Chimique de France, 1955, p. 218
[5] Patent: CN108658937, 2018, A. Location in patent: Paragraph 0151; 0152; 0231; 0232

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