Conditions | Yield |
---|---|
With phenylphosphorus tetrachloride In chloroform at 0℃; for 0.0833333h; | 98% |
With 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine at 0 - 20℃; for 3.25h; | 95% |
With 1,3,5-trichloro-2,4,6-triazine In acetonitrile at -10 - 25℃; for 5h; Solvent; Temperature; | 94% |
tetrachloromethane
tri(cyclopropylmethyl)phosphite
A
3-butenyl chloride
B
Phosphoric acid tricyclopropylmethyl ester
C
Trichloromethyl-phosphonic acid dicyclopropylmethyl ester
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In toluene at 80℃; Further byproducts given; | A 16% B 2% C 80% D 64% |
Cyclopropylmethanol
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
A 15% B 18% C 80% |
cyclopropylmethyl
A
3-butenyl chloride
B
1,3-dichlorobutane
C
1,2,4-trichlorobutane
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With chlorine In benzene Rate constant; Product distribution; Irradiation; other chlorinating agents; | A 10.3% B 6.2% C 19.1% D 34.4% |
methylcyclopropane
A
3-butenyl chloride
B
1,3-dichlorobutane
C
1,2,4-trichlorobutane
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With chlorine In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃; Irradiation; | A 10.3% B 6.2% C 19.1% D 34.4% |
With tert-butylhypochlorite In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃; for 2.5h; Irradiation; | A 17% B 3.2% C 6.5% D 24.2% |
Conditions | Yield |
---|---|
With phosphorus pentachloride | |
With hydrogenchloride |
Conditions | Yield |
---|---|
With chlorine Irradiation; | |
With chlorine at -196.1℃; Quantum yield; Irradiation; var. magnetic field; |
chlorocyclobutane
potassium acetate
acetic acid
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 100℃; Rate constant; Solvolyse und Isomerisierung; |
diazomethane
3-chloroprop-1-ene
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
Cu catalyst |
3,4-dichlorobut-1-ene
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
(i) 9-bora-bicyclo<3.3.1>nonane, THF, (ii) aq. NaOH; Multistep reaction; |
tetrachloromethane
tri(cyclopropylmethyl)phosphite
A
3-butenyl chloride
B
Dicyclopropylcarbinyl-phosphonat
C
Phosphoric acid tricyclopropylmethyl ester
D
Trichloromethyl-phosphonic acid dicyclopropylmethyl ester
E
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In toluene at 80℃; for 4h; Product distribution; Mechanism; | A 16 % Chromat. B 2 % Chromat. C 2 % Chromat. D 80 % Chromat. E 64 % Chromat. |
ethanol
3-cyclopropylmethoxy-3-chlorodiaziridine
A
3-butenyl chloride
B
allylcarbinyl ethyl ether
C
chlorocyclobutane
D
cyclobutyl ethyl ether
E
cyclopropylcarbinyl ethyl ether
F
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In ethanol; acetonitrile at 25℃; Thermodynamic data; Kinetics; Product distribution; Ea, effect of solvents; |
ethanol
3-cyclopropylmethoxy-3-chlorodiaziridine
A
allylcarbinyl ethyl ether
B
cyclobutyl ethyl ether
C
cyclopropylcarbinyl ethyl ether
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 25℃; Further byproducts given; | A 1 % Chromat. B 22 % Chromat. C 28 % Chromat. D 42 % Chromat. |
ethanol
3-cyclopropylmethoxy-3-chlorodiaziridine
A
chlorocyclobutane
B
cyclobutyl ethyl ether
C
cyclopropylcarbinyl ethyl ether
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 25℃; Further byproducts given; | A 5 % Chromat. B 22 % Chromat. C 28 % Chromat. D 42 % Chromat. |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrahydroborate; mercury dichloride 1.) CH2Cl2, 20 deg C, 2.) 20 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
cyclopropylcarbinol hypochlorite
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With triphenyl phosphite In dichloromethane at -78℃; | A 1.5 % Chromat. B 8.5 % Chromat. C 90 % Chromat. |
cyclobutyl hypochlorite
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With triphenyl phosphite In dichloromethane at -78℃; | A 5 % Chromat. B 29 % Chromat. C 66 % Chromat. |
3-cyclopropylmethoxy-3-chlorodiaziridine
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In acetonitrile at 25℃; | A 7 % Chromat. B 15 % Chromat. C 78 % Chromat. |
With tetrabutylammonium tetrafluoroborate In acetonitrile at 25℃; | A 9 % Chromat. B 27 % Chromat. C 64 % Chromat. |
With tetrabutylammonium tetrafluoroborate In acetonitrile at 25℃; | A 9 % Chromat. B 27 % Chromat. C 64 % Chromat. |
methylcyclopropane
chlorine
A
3-butenyl chloride
B
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at -20℃; | |
at 50℃; |
thionyl chloride
Cyclopropylmethanol
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
pyridine
thionyl chloride
Cyclopropylmethanol
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
thionyl chloride
cyclobutanol
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
pyridine
thionyl chloride
cyclobutanol
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
ethanol
A
chlorocyclobutane
B
cyclobutyl ethyl ether
C
cyclopropylcarbinyl ethyl ether
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 25℃; Product distribution; Further Variations:; Solvents; |
ethanol
cyclobutoxychlorocarbene
A
chlorocyclobutane
B
cyclobutyl ethyl ether
C
cyclopropylcarbinyl ethyl ether
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 25℃; Product distribution; Further Variations:; Solvents; |
Conditions | Yield |
---|---|
In acetonitrile at 25℃; Product distribution; Kinetics; Further Variations:; Solvents; | |
In 1,2-dichloro-ethane at 25℃; Kinetics; | |
In acetonitrile at 25℃; Product distribution; Further Variations:; Solvents; | A 10 % Chromat. B 19 % Chromat. C 71 % Chromat. |
cyclobutoxychlorocarbene
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 25℃; Kinetics; | |
In acetonitrile at 25℃; Product distribution; Kinetics; Further Variations:; Solvents; | |
In acetonitrile at 25℃; Product distribution; Further Variations:; Solvents; | A 10 % Chromat. B 35 % Chromat. C 55 % Chromat. |
3-cyclopropylmethoxy-3-chlorodiaziridine
A
3-butenyl chloride
B
chlorocyclobutane
C
1,4-dichlorobutane
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 365℃; Product distribution; | A 4.9 % Chromat. B 22.9 % Chromat. C 28.9 % Chromat. D 43.4 % Chromat. |
5,6-bis(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
100% |
1-(4-hydroxy-2,6-dimethylphenyl)ethanone
chloro(cyclopropyl)methane
1-(4-(cyclopropylmethoxy)-2,6-dimethylphenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; | 99% |
4-cyanophenol
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; | 98% |
6-nitro-3,4-dihydro-1H-quinolin-2-one
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
Stage #1: 6-nitro-3,4-dihydro-1H-quinolin-2-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: chloro(cyclopropyl)methane With potassium iodide In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; | 94% |
Stage #1: 6-nitro-3,4-dihydro-1H-quinolin-2-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: chloro(cyclopropyl)methane With potassium iodide In N,N-dimethyl-formamide at 120℃; for 2h; | 94% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; | 94% |
Stage #1: 6-nitro-3,4-dihydro-1H-quinolin-2-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: chloro(cyclopropyl)methane With potassium iodide In N,N-dimethyl-formamide at 120℃; Inert atmosphere; | 94% |
5-(3-fluoro-4-methoxyphenyl)-6-(4-methoxyphenyl)-2H-pyridazin-3-one
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
93.8% |
N-norcodeine hydrochloride
chloro(cyclopropyl)methane
17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-3-methoxymorphinan-6α-ol
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 18h; | 93% |
6-(3-fluoro-4-methoxyphenyl)-5-(4-methoxyphenyl)-2H-pyridazine-3-one
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
93% |
11-oxo(10H)-pyrrolo<2,1-c><1,2,5>benzothiadiazepine 5,5-dioxide
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone for 24h; Ambient temperature; | 90% |
Conditions | Yield |
---|---|
With 1-Phenylprop-1-yne; copper dichloride In tetrahydrofuran at 70℃; for 12h; | 90% |
chloro(cyclopropyl)methane
6-bromo-2-(2-cyclopropanemethyl)isoquinolin-1(2H)-one
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; | 90% |
chloro(cyclopropyl)methane
5,6-bis(4-Methoxyphenyl)-4-ethoxy-carbonyl-2H-pyridazin-3-one
5,6-bis(4-methoxyphenyl)-2-cyclopropylmethyl-4-ethoxycarbonyl-2H-pyridazin-3-one
Conditions | Yield |
---|---|
89.1% |
Conditions | Yield |
---|---|
Stage #1: (1r,4r)-4-(tritylamino)cyclohexanol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: chloro(cyclopropyl)methane In tetrahydrofuran at 20℃; for 6h; | 86.4% |
chloro(cyclopropyl)methane
(-)-17-(cyclopropylmethyl)-3,14β-dimethoxy-4,5-α-epoxy-5β-methylmorphinan-6-one
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 22h; | 86% |
chloro(cyclopropyl)methane
AR-M390
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 25℃; for 0.5h; | 86% |
Conditions | Yield |
---|---|
With phenylphosphorus tetrachloride In chloroform at 0℃; for 0.0833333h; | 98% |
With 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine at 0 - 20℃; for 3.25h; | 95% |
With 1,3,5-trichloro-2,4,6-triazine In acetonitrile at -10 - 25℃; for 5h; Solvent; Temperature; | 94% |
tetrachloromethane
tri(cyclopropylmethyl)phosphite
A
3-butenyl chloride
B
Phosphoric acid tricyclopropylmethyl ester
C
Trichloromethyl-phosphonic acid dicyclopropylmethyl ester
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In toluene at 80℃; Further byproducts given; | A 16% B 2% C 80% D 64% |
Cyclopropylmethanol
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
A 15% B 18% C 80% |
cyclopropylmethyl
A
3-butenyl chloride
B
1,3-dichlorobutane
C
1,2,4-trichlorobutane
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With chlorine In benzene Rate constant; Product distribution; Irradiation; other chlorinating agents; | A 10.3% B 6.2% C 19.1% D 34.4% |
methylcyclopropane
A
3-butenyl chloride
B
1,3-dichlorobutane
C
1,2,4-trichlorobutane
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With chlorine In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃; Irradiation; | A 10.3% B 6.2% C 19.1% D 34.4% |
With tert-butylhypochlorite In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃; for 2.5h; Irradiation; | A 17% B 3.2% C 6.5% D 24.2% |
Conditions | Yield |
---|---|
With phosphorus pentachloride | |
With hydrogenchloride |
Conditions | Yield |
---|---|
With chlorine Irradiation; | |
With chlorine at -196.1℃; Quantum yield; Irradiation; var. magnetic field; |
chlorocyclobutane
potassium acetate
acetic acid
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 100℃; Rate constant; Solvolyse und Isomerisierung; |
diazomethane
3-chloroprop-1-ene
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
Cu catalyst |
3,4-dichlorobut-1-ene
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
(i) 9-bora-bicyclo<3.3.1>nonane, THF, (ii) aq. NaOH; Multistep reaction; |
tetrachloromethane
tri(cyclopropylmethyl)phosphite
A
3-butenyl chloride
B
Dicyclopropylcarbinyl-phosphonat
C
Phosphoric acid tricyclopropylmethyl ester
D
Trichloromethyl-phosphonic acid dicyclopropylmethyl ester
E
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In toluene at 80℃; for 4h; Product distribution; Mechanism; | A 16 % Chromat. B 2 % Chromat. C 2 % Chromat. D 80 % Chromat. E 64 % Chromat. |
ethanol
3-cyclopropylmethoxy-3-chlorodiaziridine
A
3-butenyl chloride
B
allylcarbinyl ethyl ether
C
chlorocyclobutane
D
cyclobutyl ethyl ether
E
cyclopropylcarbinyl ethyl ether
F
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In ethanol; acetonitrile at 25℃; Thermodynamic data; Kinetics; Product distribution; Ea, effect of solvents; |
ethanol
3-cyclopropylmethoxy-3-chlorodiaziridine
A
allylcarbinyl ethyl ether
B
cyclobutyl ethyl ether
C
cyclopropylcarbinyl ethyl ether
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 25℃; Further byproducts given; | A 1 % Chromat. B 22 % Chromat. C 28 % Chromat. D 42 % Chromat. |
ethanol
3-cyclopropylmethoxy-3-chlorodiaziridine
A
chlorocyclobutane
B
cyclobutyl ethyl ether
C
cyclopropylcarbinyl ethyl ether
D
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
at 25℃; Further byproducts given; | A 5 % Chromat. B 22 % Chromat. C 28 % Chromat. D 42 % Chromat. |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrahydroborate; mercury dichloride 1.) CH2Cl2, 20 deg C, 2.) 20 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
cyclopropylcarbinol hypochlorite
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With triphenyl phosphite In dichloromethane at -78℃; | A 1.5 % Chromat. B 8.5 % Chromat. C 90 % Chromat. |
cyclobutyl hypochlorite
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
With triphenyl phosphite In dichloromethane at -78℃; | A 5 % Chromat. B 29 % Chromat. C 66 % Chromat. |
3-cyclopropylmethoxy-3-chlorodiaziridine
A
3-butenyl chloride
B
chlorocyclobutane
C
chloro(cyclopropyl)methane
Conditions | Yield |
---|---|
In acetonitrile at 25℃; | A 7 % Chromat. B 15 % Chromat. C 78 % Chromat. |
With tetrabutylammonium tetrafluoroborate In acetonitrile at 25℃; | A 9 % Chromat. B 27 % Chromat. C 64 % Chromat. |
With tetrabutylammonium tetrafluoroborate In acetonitrile at 25℃; | A 9 % Chromat. B 27 % Chromat. C 64 % Chromat. |
IUPAC Name:chloromethylcyclopropane
Molecular Formula:C4H7Cl
Molecular Weight:90.551380 g/mol
Appearance:colorless liquid
Melting Point:-91°C
Boiling Point:87-89 °C(lit.)
Flash Point:29 °F
Water Solubility:1165 mg/L at 25 °C
Density:0.98 g/mL at 25 °C(lit.)
Refractive index:n20/D 1.435(lit.)
BRN:635697
EINECS:227-632-1
Synonyms of Cylopropylmethyl chloride(5911-08-0):
CYCLOPROPYLMETHYL CHLORIDE;(CHLOROMETHYL)CYCLOPROPANE;Cyclopropane, (chloromethyl)-;Cyclopropane,(chloromethyl);Cylopropylmethylchloride;Cyclopropylmethychloride;Cyclopropylmethyl Chloride, Pract.;CPMCl
Categories of Cylopropylmethyl chloride(5911-08-0):
Cycloalkanes;Alkyl;Halogenated Hydrocarbons;Organic Building Blocks
First Aid Measures of Cylopropylmethyl chloride(5911-08-0):
Ingestion:If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Skin:Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Remove contaminated clothing and shoes.
Eyes:Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Storage of Cylopropylmethyl chloride(5911-08-0):
Keep away from heat, sparks, and flame. Flammables-area.
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