4-(2-Chloroethyl)morpholine supplier

Name
4-(2-Chloroethyl)morpholine
EINECS 221-810-2
CAS No. 3240-94-6
Article Data37
CAS DataBase
Density 1.088 g/cm³
Solubility
Melting Point
Formula C₆H₁₂ClNO
Boiling Point 202.8 °C at 760 mmHg
Molecular Weight 149.62
Flash Point 76.4 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 12.47000
LogP 1.29730

Synthetic route

: 622-40-2
2-(morpholin-4-yl)ethanol

: 3240-94-6
N-(2-chlorethyl)morpholine

Conditions

Conditions	Yield
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

Conditions	Yield
With potassium carbonate In water	84%
With potassium carbonate In water	69%
With potassium hydroxide In water	59%

: 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

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

...Expand

: 110-91-8
morpholine

: 107-04-0
1-Bromo-2-chloroethane

: 3240-94-6
N-(2-chlorethyl)morpholine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	20%
With potassium carbonate In acetonitrile at 20℃;

: 186581-53-3, 908094-01-9
diazomethane

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 3240-94-6
N-(2-chlorethyl)morpholine

: 19438-10-9
methyl 3-hydroxybenzoate

: 249937-00-6
methyl 3-(2-morpholinyl-4-ylethoxy)benzoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	100%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 2-carbomethoxy-4(5)-phenylimidazole

: 1355966-76-5
C17H21N3O3

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	100%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 52427-05-1
2-bromo-5-nitrophenol

: 1610875-62-1
4-(2-(2-bromo-5-nitrophenoxy)ethyl)morpholine

Conditions

Conditions	Yield
Stage #1: 2-bromo-5-nitrophenol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: N-(2-chlorethyl)morpholine In N,N-dimethyl-formamide at 20 - 70℃;	100%

: 3240-94-6
N-(2-chlorethyl)morpholine

: Phenyl 4-pyridyl ketone oxime

: C18H21N3O2

Conditions

Conditions	Yield
Stage #1: Phenyl 4-pyridyl ketone oxime With sodium hydride In water; N,N-dimethyl-formamide at 10 - 15℃; for 1h; Stage #2: N-(2-chlorethyl)morpholine In water; N,N-dimethyl-formamide at 20℃; for 2h;	100%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 126410-13-7
N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-(4-hydroxyphenyl)-2(R)-<(4-hydroxyphenyl)methyl>hexanamide

: 138483-73-5
N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-<4-<2-(4-morpholinyl)ethoxy>phenyl>-2(R)-<<4-<2-(4-morpholinyl)ethoxy>phenyl>methyl>hexanamide

Conditions

Conditions	Yield
With caesium carbonate In 1,4-dioxane at 80℃; for 4h;	99%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 4-bromo-6-hydroxypyrazolo[ 1,5-a]pyridine-3-carbonitrile

: 4-bromo-6-(2-morpholinoethoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 50℃; for 72h;	99%
With potassium carbonate In N,N-dimethyl acetamide at 50℃; for 72h;	99%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 138498-62-1
N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[1,1-dimethylethoxy-carbonylamino]-4(S)-hydroxy-6-phenyl-2(R)-(4-hydroxyphenylmethyl) hexanamide

: 138483-63-3
L-689502

Conditions

Conditions	Yield
With caesium carbonate In 1,4-dioxane at 80℃; for 36h;	98.9%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 619-45-4
4-methoxycarbonyl aniline

: 4-(2-Morpholin-4-yl-ethylamino)-benzoic acid methyl ester

Conditions

Conditions	Yield
With potassium iodide In acetonitrile at 170℃; under 4875.39 Torr; for 0.166667h; microwave irradiation;	98%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 610-78-6
3-nitro-4-chlorophenol

: 223442-48-6
4-(2-(4-chloro-3-nitrophenoxy)ethyl)morpholine

Conditions

Conditions	Yield
With caesium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 20h;	96%
With Ki; caesium carbonate In N-methyl-acetamide

: 3240-94-6
N-(2-chlorethyl)morpholine

: 3446-72-8
5-chloro-2-methyl-1H-indole-3-acetic acid ethyl ester

: ethyl 2-(5-chloro-2-methyl-1-(2-morpholinoethyl)-1H-indol-3-yl)acetate

Conditions

Conditions	Yield
Stage #1: 5-chloro-2-methyl-1H-indole-3-acetic acid ethyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: N-(2-chlorethyl)morpholine In N,N-dimethyl-formamide at 45℃; Inert atmosphere;	96%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 4-(3-methoxyphenyl)naphthalen-1-ol

: 4-(2-(1-(3-methoxyphenyl)naphthalen-4-yloxy)ethyl)morpholine

Conditions

Conditions	Yield
Stage #1: 4-(3-methoxyphenyl)naphthalen-1-ol With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: N-(2-chlorethyl)morpholine In N,N-dimethyl-formamide at 100℃; for 8h;	96%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 100-61-8
N-methylaniline

: 79049-81-3
N-methyl-N-[3-(N'-morpholyl)ethyl]aniline

Conditions

Conditions	Yield
With potassium iodide In acetonitrile at 110℃; under 825.066 Torr; for 0.166667h; microwave irradiation;	95%
at 200℃;

: 3240-94-6
N-(2-chlorethyl)morpholine

: 371-40-4
4-fluoroaniline

: (4-fluoro-phenyl)-(2-morpholin-4-yl-ethyl)-amine

Conditions

Conditions	Yield
With potassium iodide In acetonitrile at 170℃; under 4875.39 Torr; for 0.166667h; microwave irradiation;	95%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 914224-34-3
2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazol-7-ol

: 950769-60-5
4-(2-((2-(4-nitrophenyl)benzo[d]imidazo[2,1-b]thiazol-7-yl)oxy)ethyl)morpholine

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 5h;	95%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 24036-52-0
6-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one

: 6-bromo-4-(2-morpholinoethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h;	94.1%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 1,3,3-trimethyl-5-(phenylmethylene)-2-oxabicyclo<2.2.2>octan-6-one oxime (II)

: 1,3,3-Trimethyl-5-[1-phenyl-meth-(E)-ylidene]-2-oxa-bicyclo[2.2.2]octan-6-one O-(2-morpholin-4-yl-ethyl)-oxime

Conditions

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide 1.) methanol, reflux, 30 min; 2.) 50 deg C, 3 h; r.t., 12 h;	94%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 1105056-24-3
9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one

: 1436402-36-6
C34H29NO7

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere;	94%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 79420-48-7
7-hydroxy-1,2,3,4-tetrahydrocyclopenta(b)benzopyran-4-one

: 146857-62-7
6-(2-Morpholin-4-yl-ethoxy)-2,3-dihydro-1H-cyclopenta[b]chromen-9-one

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	93%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 2,3-dihydro-6-mercapto-1,3,5-triphenyl-2-thioxo-4(3H)-pyrimidinone

: 6-(2-morpholin-4-yl-ethylsulfanyl)-1,3,5-triphenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60 - 65℃; for 4h;	93%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 116776-59-1
6-(4-Fluoro-phenyl)-4-phenyl-2H-pyridazin-3-one

: 127588-46-9
6-(4-Fluoro-phenyl)-2-(2-morpholin-4-yl-ethyl)-4-phenyl-2H-pyridazin-3-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;	92%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 496-15-1
1-indoline

: 1-(2-morpholin-4-yl-ethyl)-2,3-dihydro-1H-indole

Conditions

Conditions	Yield
With potassium iodide In acetonitrile at 110℃; under 825.066 Torr; for 0.166667h; microwave irradiation;	92%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 104-94-9
4-methoxy-aniline

: 4-methoxy-N-(2-morpholinoethyl)aniline

Conditions

Conditions	Yield
With potassium iodide In acetonitrile at 110℃; under 825.066 Torr; for 0.166667h; microwave irradiation;	92%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 1092361-69-7
C18H17F3NOS2(1-)*Na(1+)

: 1092361-75-5
N-methyl-3-phenyl-3-[4-(trifluoromethyl)-phenoxy]-propylamine carbodithioic acid S-[2-morpholino-ethyl] ester

Conditions

Conditions	Yield
In methanol at 20℃; for 12h;	92%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 6-bromo-N-(4-methylcyclohexyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

: 6-bromo-N-(4-methylcyclohexyl)-1-[2-(morpholin-4-yl)ethyl]-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 6-bromo-N-(4-methylcyclohexyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(2-chlorethyl)morpholine In N,N-dimethyl-formamide at 50℃; for 12h;	92%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 149-30-4
2-Mercaptobenzothiazole

: 97406-76-3
2-(2-morpholin-4-yl-ethylsulfanyl)-benzothiazole

Conditions

Conditions	Yield
With aluminum oxide at 50℃; neat (no solvent);	91.6%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 100-02-7
4-nitro-phenol

: 65300-53-0
4-[2-(4-nitrophenoxy)ethyl]morpholine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 2.5h; Reflux;	91%
With ethanol; sodium ethanolate
Stage #1: 4-nitro-phenol With potassium hydroxide In ethanol at 20℃; for 2h; Stage #2: N-(2-chlorethyl)morpholine In toluene for 24h; Reflux;

: 3240-94-6
N-(2-chlorethyl)morpholine

: 99-93-4
4-Hydroxyacetophenone

: 2079-50-7
1-(4-(2-morpholinoethoxy)phenyl)ethanone

Conditions

Conditions	Yield
Stage #1: N-(2-chlorethyl)morpholine; 4-Hydroxyacetophenone With sodium ethanolate In ethanol at 20℃; for 17h; Heating / reflux; Stage #2: With hydrogenchloride In water Stage #3: With sodium hydroxide; water	91%
With ethanol; sodium ethanolate
With potassium carbonate In acetone at 60℃;

: 3240-94-6
N-(2-chlorethyl)morpholine

: 126456-38-0
N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-(4-hydroxyphenyl)-2(R)-(phenylmethyl)hexanamide

: 138483-72-4
N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-<(tert-butyloxycarbonyl)amino>-4(S)-hydroxy-6-<4-<2-(4-morpholinyl)ethoxy>phenyl>-2(R)-(phenylmethyl)hexanamide

Conditions

Conditions	Yield
With caesium carbonate In 1,4-dioxane at 80℃; for 3h;	91%

: 3240-94-6
N-(2-chlorethyl)morpholine

: 1100642-23-6
N-(1H-benzimidazol-2-ylmethyl)-2-chloro-9H-purin-6-amine

: 1133758-63-0
N-(1H-benzimidazol-2-ylmethyl)-2-chloro-9-(2-morpholin-4-ylethyl)-9H-purin-6-amine

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	91%

4-(2-Chloroethyl)morpholine 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 NO_x. 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.

Product Name

4-(2-Chloroethyl)morpholine

Synthetic route

4-(2-Chloroethyl)morpholine Specification

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