4-(2-Chloroethyl)morpholine hydrochloride

Product Name4-(2-Chloroethyl)morpholine hydrochloride
CAS3647-69-6
MFC6H13Cl2NO
MW186.08
EINECS222-881-2
MOL File3647-69-6.mol

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	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29349990
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Acute Tox. 4 Dermal Aquatic Chronic 3 Eye Dam. 1 Skin Corr. 1B Skin Sens. 1
Toxicity	LD50 orally in Rabbit: 96 mg/kg LD50 dermal Rat 1502 mg/kg

MSDS

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

Usage And Synthesis

Chemical Properties

White to beige crystalline powder

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.

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.

Safety Profile

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

Synthesis

110-91-8

107-07-3

4-(2-Chloroethyl)morpholine hydrochloride

3647-69-6

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

4-(2-Chloroethyl)morpholine hydrochloride

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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