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3240-94-6

Basic Information
CAS No.: 3240-94-6
Name: 4-(2-Chloroethyl)morpholine
Article Data: 37
Molecular Structure:
Molecular Structure of 3240-94-6 (4-(2-Chloroethyl)morpholine)
Formula: C6H12ClNO
Molecular Weight: 149.62
Synonyms: 1-Chloro-2-morpholinoethane;1-Morpholino-2-chloroethane;2-(4-Morpholinyl)ethyl chloride;2-Morpholino-1-chloroethane;2-Morpholinoethyl chloride;4-(2-Chloroethyl)morpholine;Morpholinoethyl chloride;N-(2-Chloroethyl)morpholine;N-(Chloroethyl)morpholine;b-Chloroethylmorpholine;b-Morpholinoethyl chloride;
EINECS: 221-810-2
Density: 1.088 g/cm3
Boiling Point: 202.8 °C at 760 mmHg
Flash Point: 76.4 °C
PSA: 12.47000
LogP: 1.29730
Synthetic route
622-40-2

2-(morpholin-4-yl)ethanol

3240-94-6

N-(2-chlorethyl)morpholine

Conditions
ConditionsYield
With thionyl chloride In toluene at 0℃; for 10h; Reflux;89%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 40℃;74%
With thionyl chloride In dichloromethane at 0 - 40℃;43.85%
3647-69-6

4-(2-chloroethyl)morpholine hydrochride

3240-94-6

N-(2-chlorethyl)morpholine

Conditions
ConditionsYield
With potassium carbonate In water84%
With potassium carbonate In water69%
With potassium hydroxide In water59%
110-91-8

morpholine

107-06-2

1,2-dichloro-ethane

A

3240-94-6

N-(2-chlorethyl)morpholine

B

1723-94-0

1,2-dimorpholylethane

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 70 - 80℃; for 2.5h;A 30%
B 22%
110-91-8

morpholine

107-04-0

1-Bromo-2-chloroethane

3240-94-6

N-(2-chlorethyl)morpholine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;20%
With potassium carbonate In acetonitrile at 20℃;
16158-87-5

N-(chloromethyl)morpholine

3240-94-6

N-(2-chlorethyl)morpholine

110-91-8

morpholine

107-20-0

2-chloroethanal

3240-94-6

N-(2-chlorethyl)morpholine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane; water for 2h; Ambient temperature;
whose hydrochloride

whose hydrochloride

3240-94-6

N-(2-chlorethyl)morpholine

Conditions
ConditionsYield
With thionyl chloride; chloroform
With thionyl chloride; benzene
With tetrachloromethane; thionyl chloride

5-(3-methoxy-4-fluoromethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

A

3240-94-6

N-(2-chlorethyl)morpholine

B

519015-10-2

2-morpholinoethyl-5-(3-methoxy-4-fluoromethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

110-91-8

morpholine

540-51-2

2-bromoethanol

3240-94-6

N-(2-chlorethyl)morpholine

Conditions
ConditionsYield
Stage #1: morpholine; 2-bromoethanol With triethylamine In toluene at 80℃; for 4h;
Stage #2: With thionyl chloride In dichloromethane at 0 - 80℃; for 2h;
Stage #1: morpholine; 2-bromoethanol With potassium carbonate In acetonitrile at 75℃; for 16h;
Stage #2: With thionyl chloride; 1,2-dichloro-ethane In 1,2-dichloro-ethane at 80℃; for 16h;
3240-94-6

N-(2-chlorethyl)morpholine

1687-53-2

5-amino-2-methoxyphenol

170229-80-8

4-methoxy-3-(2-morpholinoethoxy)aniline

Conditions
ConditionsYield
In pyridine; DMF (N,N-dimethyl-formamide) at 20 - 60℃;100%
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Specification

The IUPAC name of this chemical is 4-(2-chloroethyl)morpholine. With the CAS registry number 3240-94-6 and EINECS 221-810-2, it is also named as 2-(4-Morpholinyl)ethyl chloride. The classification codes are Drug / Therapeutic Agent; Mutation data; TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]. This chemical is highly toxic. When heated to decomposition it emits toxic fumes of Cl and NOx. So the storage environment should be well-ventilated, low-temperature and dry. Keep 4-(2-Chloroethyl)morpholine separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.93; (4)ACD/LogD (pH 7.4): 0.19; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.1; (8)ACD/KOC (pH 7.4): 28.02; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.461; (13)Molar Refractivity: 37.79 cm3; (14)Molar Volume: 137.5 cm3; (15)Polarizability: 14.98×10-24 cm3; (16)Surface Tension: 31.6 dyne/cm; (17)Enthalpy of Vaporization: 43.9 kJ/mol; (18)Vapour Pressure: 0.288 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 149.060742; (21)MonoIsotopic Mass: 149.060742; (22)Topological Polar Surface Area: 12.5; (23)Heavy Atom Count: 9; (24)Complexity: 73.5.

Uses of 4-(2-Chloroethyl)morpholine: It can react with 2-morpholin-4-yl-ethanol to get 4,4'-(3-oxa-pentane-1,5-diyl)-bis-morpholine. This reaction needs reagent 50percent NaOH, catalytic agent Adogen 464 and solvent tetrahydrofuran by heating. The reaction time is 6 hours. The yield is 84%.

People can use the following data to convert to the molecule structure. 
1. SMILES:ClCCN1CCOCC1
2. InChI:InChI=1/C6H12ClNO/c7-1-2-8-3-5-9-6-4-8/h1-6H2
3. InChIKey:ZAPMTSHEXFEPSD-UHFFFAOYAJ

The following are the toxicity data which has been tested. 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LCLo inhalation 370mg/m3/10M (370mg/m3)   National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. NOV1942,
rat LD50 unreported 70mg/kg (70mg/kg)   Pharmaceutical Bulletin. Vol. 1, Pg. 297, 1953.