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4-(2-Chloroethyl)morpholine hydrochloride

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Name

4-(2-Chloroethyl)morpholine hydrochloride

EINECS 222-881-2
CAS No. 3647-69-6 Density 1.088g/cm3
PSA 12.47000 LogP 1.29730
Solubility Soluble in water Melting Point 180-185 °C (dec.)(lit.)
Formula C6H12ClNO.HCl Boiling Point 202.8 °C at 760 mmHg
Molecular Weight 186.081 Flash Point 76.4 °C
Transport Information UN 2923 8/PG 3 Appearance White to beige crystalline powder
Safety 26-36/37/39-45-61 Risk Codes 21-25-34-43-52/53
Molecular Structure Molecular Structure of 3647-69-6 (4-(2-Chloroethyl)morpholine hydrochloride) Hazard Symbols ToxicT
Synonyms

Morpholine,4-(2-chloroethyl)-, hydrochloride (6CI,7CI,8CI,9CI);1-(Morpholin-4-yl)-2-chloroethane hydrochloride;1-Chloro-2-morpholinoethanehydrochloride;2-(4-Morpholinyl)ethyl chloride hydrochloride;2-Morpholinoethylchloride hydrochloride;4-(2-Chloroethyl)morpholine monohydrochloride;4-(2-Chloroethyl)morpholiniumchloride;Morpholinoethyl chloride hydrochloride;N-(2-Chloroethyl)morpholinehydrochloride;N-(b-Chloroethyl)morpholine hydrochloride;b-Morpholinoethyl chloride hydrochloride;

Article Data 5

4-(2-Chloroethyl)morpholine hydrochloride Synthetic route

5-hydroxymethyl-6-methylazepino[4,5-b]indole

A

1,2,3,4,5,6-hexahydro-3-morpholinoethyl-5-hydroxymethyl-6-methylazepino[4,5-b]indole

B

3647-69-6

4-(2-chloroethyl)morpholine hydrochride

trans-4-Bromo-N-methyl-N-[4-(2-morpholin-4-yl-ethoxy)-cyclohexyl]-benzenesulfonamide

A

trans-4-Bromo-N-(4-hydroxy-cyclohexyl)-N-methyl-benzenesulfonamide

B

3647-69-6

4-(2-chloroethyl)morpholine hydrochride

trans-N-Methyl-N-[4-(2-morpholin-4-yl-ethoxy)-cyclohexyl]-4-trifluoromethyl-benzenesulfonamide

A

trans-N-(4-hydroxy-cyclohexyl)-N-methyl-4-trifluoro-methyl-benzenesulfonamide

B

3647-69-6

4-(2-chloroethyl)morpholine hydrochride

110-91-8

morpholine

107-07-3

2-chloro-ethanol

3647-69-6

4-(2-chloroethyl)morpholine hydrochride

Conditions
ConditionsYield
With thionyl chloride; sodium hydroxide In toluene for 5h; Reflux;
Stage #1: morpholine; 2-chloro-ethanol In toluene for 2h; Reflux;
Stage #2: With thionyl chloride In toluene at 20℃; for 6.33h; Cooling with ice;
7.9 g
622-40-2

2-(morpholin-4-yl)ethanol

3647-69-6

4-(2-chloroethyl)morpholine hydrochride

Conditions
ConditionsYield
With thionyl chloride In chloroform Reflux; Cooling with ice;
3647-69-6

4-(2-chloroethyl)morpholine hydrochride

(3R,4R)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3-(7-hydroxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

(3R,4R)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3-[7-(2-morpholin-4-yl-ethoxy)-naphthalen-2-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h;100%
3647-69-6

4-(2-chloroethyl)morpholine hydrochride

(3R,4R)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3-(6-hydroxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

(3R,4R)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3-[6-(2-morpholin-4-yl-ethoxy)-naphthalen-2-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h;100%
55289-05-9

methyl 3-hydroxy-2-methylbenzoate

3647-69-6

4-(2-chloroethyl)morpholine hydrochride

467252-57-9

methyl 2-methyl-3-(2-morpholinoethoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Heating;100%
3647-69-6

4-(2-chloroethyl)morpholine hydrochride

99-76-3

methyl 4-hydroxylbenzoate

92501-87-6

methyl 4-(2-morpholinoethoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃;100%
With caesium carbonate In acetonitrile at 80 - 85℃; for 4h; Inert atmosphere;92%
With potassium carbonate In acetone Heating;
15174-02-4

4-hydroxy-2-nitroanisole

3647-69-6

4-(2-chloroethyl)morpholine hydrochride

761440-70-4

4-[2-(4-methoxy-3-nitro-phenoxy)-ethyl]-morpholine

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In DMF (N,N-dimethyl-formamide) at 80℃; for 4h;100%

4-(2-Chloroethyl)morpholine hydrochloride Chemical Properties

Molecular Formula: C6H13Cl2NO
Formula Weight: 186.08
mp OF 4-(2-CHLOROETHYL)MORPHOLINE HYDRO CHLORIDE (3647-69-6): 180-185 °C (dec.)(lit.)
Flash Point: 76.4 °C  
Boiling Point: 202.8 °C at 760 mmHg  
Water Solubility : soluble
Vapour Pressure: 0.288 mmHg at 25°C  
Sensitive of 4-(2-CHLOROETHYL)MORPHOLINE HYDRO CHLORIDE (3647-69-6): Hygroscopic
Appearence of 4-(2-CHLOROETHYL)MORPHOLINE HYDRO CHLORIDE (3647-69-6): White to beige crystalline powder

4-(2-Chloroethyl)morpholine hydrochloride Uses

4-(2-Chloroethyl)morpholine hydro chloride (3647-69-6) (MOC) is used as intermediate for the synthesis of pharmaceuticals (e.g. floredil, morinamide, nimorazole and pholcodine).

4-(2-Chloroethyl)morpholine hydrochloride Production

4-(2-Chloroethyl)morpholine hydro chloride (3647-69-6) is obtained by thionyl chloride chlorination reaction with morpholine ethanol, which is get from the addition reaction of morpholine and epoxy ethane.

4-(2-Chloroethyl)morpholine hydrochloride Toxicity Data With Reference

1.    

mmo-sat 21,500 nmol/L

    ENMUDM    Environmental Mutagenesis. 3 (1981),11.
2.    

mmo-esc 21,500 nmol/L

    ENMUDM    Environmental Mutagenesis. 3 (1981),11.
3.    

dns-rat:lvr 100 µmol/L

    ENMUDM    Environmental Mutagenesis. 3 (1981),11.
4.    

msc-mus:lym 44 µmol/L

    ENMUDM    Environmental Mutagenesis. 3 (1981),33.

4-(2-Chloroethyl)morpholine hydrochloride Consensus Reports

Reported in EPA TSCA Inventory.

4-(2-Chloroethyl)morpholine hydrochloride Safety Profile

Safety: WARNING: Irreversible damage risk, protect skin/eyes/lungs.
Hazard Codes : T (Toxic)
Risk Statements : 21-25-34-43-52/53 (Harmful in contact with skin; Toxic if swallowed; Causes burns; May cause sensitization by skin contact; Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment)
Safety Statements : 26-36/37/39-45-61 (In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; Wear suitable protective clothing, gloves and eye/face protection; In case of accident or if you feel unwell, seek medical advice immediately; Avoid release to the environment. Refer to special instructions safety data sheet)
RIDADR : UN 2923 8/PG 3
WGK Germany : 2
RTECS : QE0260000
PackingGroup : III
HS Code : 29349990
Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl and NOx.

4-(2-Chloroethyl)morpholine hydrochloride Specification

Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep container closed when not in use.

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