4-(2-Chloroethyl)morpholine hydrochloride

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CAS:3647-69-6
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CAS:3647-69-6
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CAS:3647-69-6

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4-(2-Chloroethyl)morpholine hydrochloride Basic information
Product Name:4-(2-Chloroethyl)morpholine hydrochloride
Synonyms:4-(2-chloroethyl)-morpholinhydrochloride;MOCPRF;MORPHOLINOETHYL CHLORIDE HYDROCHLORIDE;N-(2-CHLOROETHYL)MORPHOLINE HYDROCHLORIDE;N-(2-CHLORETHYL)-MORPHOLINIUM CHLORIDE;4-(2-CHLOROETHYL)MORPHOLINE HYDROCHLORIDE;2-MORPHOLINOETHYL CHLORIDE HYDROCHLORIDE;2-CHLOROETHYLMORPHOLINE HYDROCHLORIDE
CAS:3647-69-6
MF:C6H13Cl2NO
MW:186.08
EINECS:222-881-2
Product Categories:Aromatic Morpholines;Building Blocks;C4 to C10;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Morpholines/Thiomorpholines;Heterocycles;Pyridines
Mol File:3647-69-6.mol
4-(2-Chloroethyl)morpholine hydrochloride Structure
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
PH4.5-5 (10g/l, H2O, 20℃)
Water Solubility soluble
Sensitive Hygroscopic
BRN 3684083
InChIInChI=1S/C6H12ClNO.ClH/c7-1-2-8-3-5-9-6-4-8;/h1-6H2;1H
InChIKeyNBJHDLKSWUDGJG-UHFFFAOYSA-N
SMILESC1OCCN(CCCl)C1.[H]Cl
CAS DataBase Reference3647-69-6(CAS DataBase Reference)
EPA Substance Registry SystemMorpholine, 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 Temperature365 °C
TSCA TSCA listed
HazardClass 8
PackingGroup III
HS Code 29349990
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Oral
Acute Tox. 4 Dermal
Aquatic Chronic 3
Eye Dam. 1
Skin Corr. 1B
Skin Sens. 1
ToxicityLD50 orally in Rabbit: 96 mg/kg LD50 dermal Rat 1502 mg/kg
MSDS Information
ProviderLanguage
2-Morpholinoethyl chloride hydrochloride English
SigmaAldrich English
ACROS English
ALFA English
4-(2-Chloroethyl)morpholine hydrochloride Usage And Synthesis
Chemical PropertiesWhite to beige crystalline powder
Uses4-(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.
Uses4-(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 ProfileExperimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cland NOx.
Synthesis
Morpholine

110-91-8

2-Chloroethanol

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
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