4-(2-Chloroethyl)morpholine hydrochloride Chemical Properties

Melting point:

180-185 °C (dec.)(lit.)

storage temp. 

Store below +30°C.

solubility 

Chloroform (Slightly, Heated), Methanol (Slightly), Water (Slightly)

form 

Hygroscopic Crystalline Powder

color 

White to beige

PH

4.5-5 (10g/l, H2O, 20℃)

Water Solubility 

soluble

Sensitive 

Hygroscopic

BRN 

3684083

InChI

InChI=1S/C6H12ClNO.ClH/c7-1-2-8-3-5-9-6-4-8;/h1-6H2;1H

InChIKey

NBJHDLKSWUDGJG-UHFFFAOYSA-N

SMILES

C1OCCN(CCCl)C1.[H]Cl

CAS DataBase Reference

3647-69-6(CAS DataBase Reference)

EPA Substance Registry System

Morpholine, 4-(2-chloroethyl)-, hydrochloride (3647-69-6)

Safety Information

Hazard Codes 

T

Risk Statements 

21-25-34-43-52/53

Safety Statements 

26-36/37/39-45-61

RIDADR 

UN 2923 8/PG 3

WGK Germany 

2

RTECS 

QE0260000

Autoignition Temperature

365 °C

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29349990

Toxicity

LD50 orally in Rabbit: 96 mg/kg LD50 dermal Rat 1502 mg/kg

MSDS

• Language:English Provider:2-Morpholinoethyl chloride hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-(2-Chloroethyl)morpholine hydrochloride Usage And Synthesis

Chemical Properties

White to beige crystalline powder

Uses

4-(2-Chloroethyl)morpholine hydrochloride (MOC) is used as intermediate for the synthesis of pharmaceuticals (e.g. floredil, morinamide, nimorazole and pholcodine). It is also used as Agrochemical Intermediates, dyestuff Intermediates.

Uses

4-(2-Chloroethyl)morpholine is used in the preparation of potential DNA cross-linking antitumor agents as well as synthetic opiate analogues. 4-(2-Chloroethyl)morpholine may possess sickle-cell hemogl obin aggregation inhibiting-activity.

Safety Profile

Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cland NOx.

Synthesis

General procedure for the synthesis of N-(2-chloroethyl)morpholine hydrochloride from morpholine and 2-chloroethanol: 5.0 mL of morpholine (57.5 mmol) and 4.6 mL of 2-chloroethanol (69.0 mmol) were added to 40 mL of toluene, and heated and refluxed for 2 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and then 8.4 mL (114 mmol) of thionyl chloride was added slowly dropwise under ice bath conditions. After the dropwise addition, the reaction was continued in the ice bath for 20 min, after which the ice bath was removed and the reaction mixture was allowed to stir for 6 h at room temperature. At the end of the reaction, toluene and unreacted thionyl chloride were removed by distillation under reduced pressure. The resulting residue was recrystallized from ethanol to give 7.9 g of N-(2-chloroethyl)morpholine hydrochloride.

References

[1] Patent: US2013/85140, 2013, A1. Location in patent: Paragraph 0074; 0075
[2] Patent: CN104710394, 2017, B. Location in patent: Paragraph 0039-0041

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