5911-08-0

Basic information

• Product Name: Cylopropylmethyl chloride
• Synonyms: CYCLOPROPYLMETHYL CHLORIDE;(CHLOROMETHYL)CYCLOPROPANE;Cyclopropane, (chloromethyl)-;Cyclopropane,(chloromethyl)-;Cylopropylmethylchloride;Cyclopropylmethychloride;Cyclopropylmethyl Chloride, Pract.;CPMCl
• CAS NO: 5911-08-0
• Molecular Formula: C₄H₇Cl
• Molecular Weight: 90.55
• EINECS: 227-632-1
• Product Categories: Cycloalkanes;Alkyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 5911-08-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: -91°C
• Boiling Point: 87-89 °C(lit.)
• Flash Point: 29 °F
• Appearance: COA
• Density: 0.98 g/mL at 25 °C(lit.)
• Vapor Pressure: 71.1mmHg at 25°C
• Refractive Index: n20/D 1.435(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Not miscible in water.
• BRN: 635697
• CAS DataBase Reference: Cylopropylmethyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Cylopropylmethyl chloride(5911-08-0)
• EPA Substance Registry System: Cylopropylmethyl chloride(5911-08-0)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 5911-08-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to pale yellow liquid

Uses

Different sources of media describe the Uses of 5911-08-0 differently. You can refer to the following data:
1. (Chloromethyl)cyclopropane was used in the synthesis of (lithiomethyl)cyclopropane and homoallyllithium via 4,4?-di-tert-butylbiphenyl or naphthalene-catalysed lithiation reaction. On reaction with isolable dialkylsilylene affords 5-silaspiro[4.4]nonane derivative.
2. (Chloromethyl)cyclopropane was used in the synthesis of (lithiomethyl)cyclopropane and homoallyllithium via 4,4′-di-tert-butylbiphenyl or naphthalene-catalysed lithiation reaction.

Synthesis Reference(s)

Tetrahedron Letters, 13, p. 2135, 1972 DOI: 10.1016/S0040-4039(01)84787-0

General Description

(Chloromethyl)cyclopropane on reaction with isolable dialkylsilylene affords 5-silaspiro[4.4]nonane derivative.

InChI:InChI=1/C4H7Cl/c5-3-4-1-2-4/h4H,1-3H2

Synthetic route

Cyclopropylmethanol (2516-33-8) → chloro(cyclopropyl)methane (5911-08-0)

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 (56-23-5) + tri(cyclopropylmethyl)phosphite (112057-32-6) → 3-butenyl chloride (927-73-1) + Phosphoric acid tricyclopropylmethyl ester (27301-78-6) + Trichloromethyl-phosphonic acid dicyclopropylmethyl ester (112142-26-4) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
In toluene at 80℃; Further byproducts given;	A 16% B 2% C 80% D 64%

Cyclopropylmethanol (2516-33-8) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
	A 15% B 18% C 80%

cyclopropylmethyl (2154-76-9) → 3-butenyl chloride (927-73-1) + 1,3-dichlorobutane (1190-22-3) + 1,2,4-trichlorobutane (1790-22-3) + chloro(cyclopropyl)methane (5911-08-0)

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 (594-11-6) → 3-butenyl chloride (927-73-1) + 1,3-dichlorobutane (1190-22-3) + 1,2,4-trichlorobutane (1790-22-3) + chloro(cyclopropyl)methane (5911-08-0)

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%

Cyclopropylmethanol (2516-33-8) + cyclobutanol (2919-23-5) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
With phosphorus pentachloride
With hydrogenchloride

methylcyclopropane (594-11-6) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
With chlorine Irradiation;
With chlorine at -196.1℃; Quantum yield; Irradiation; var. magnetic field;

chlorocyclobutane (1120-57-6) + potassium acetate (127-08-2) + acetic acid (64-19-7) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at 100℃; Rate constant; Solvolyse und Isomerisierung;

diazomethane (186581-53-3, 908094-01-9) + 3-chloroprop-1-ene (107-05-1) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
Cu catalyst

3,4-dichlorobut-1-ene (310447-99-5, 310448-01-2) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
(i) 9-bora-bicyclo<3.3.1>nonane, THF, (ii) aq. NaOH; Multistep reaction;

tetrachloromethane (56-23-5) + tri(cyclopropylmethyl)phosphite (112057-32-6) → 3-butenyl chloride (927-73-1) + Dicyclopropylcarbinyl-phosphonat (6554-31-0) + Phosphoric acid tricyclopropylmethyl ester (27301-78-6) + Trichloromethyl-phosphonic acid dicyclopropylmethyl ester (112142-26-4) + chloro(cyclopropyl)methane (5911-08-0)

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 (64-17-5) + 3-cyclopropylmethoxy-3-chlorodiaziridine (122651-94-9) → 3-butenyl chloride (927-73-1) + allylcarbinyl ethyl ether (44611-46-3) + chlorocyclobutane (1120-57-6) + cyclobutyl ethyl ether (70097-82-4) + cyclopropylcarbinyl ethyl ether (70097-81-3) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
In ethanol; acetonitrile at 25℃; Thermodynamic data; Kinetics; Product distribution; Ea, effect of solvents;

ethanol (64-17-5) + 3-cyclopropylmethoxy-3-chlorodiaziridine (122651-94-9) → allylcarbinyl ethyl ether (44611-46-3) + cyclobutyl ethyl ether (70097-82-4) + cyclopropylcarbinyl ethyl ether (70097-81-3) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at 25℃; Further byproducts given;	A 1 % Chromat. B 22 % Chromat. C 28 % Chromat. D 42 % Chromat.

ethanol (64-17-5) + 3-cyclopropylmethoxy-3-chlorodiaziridine (122651-94-9) → chlorocyclobutane (1120-57-6) + cyclobutyl ethyl ether (70097-82-4) + cyclopropylcarbinyl ethyl ether (70097-81-3) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at 25℃; Further byproducts given;	A 5 % Chromat. B 22 % Chromat. C 28 % Chromat. D 42 % Chromat.

bicyclo[1.1.0]butane (157-33-5) → chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

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 (75637-38-6) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
With triphenyl phosphite In dichloromethane at -78℃;	A 1.5 % Chromat. B 8.5 % Chromat. C 90 % Chromat.

cyclobutyl hypochlorite (75637-39-7) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
With triphenyl phosphite In dichloromethane at -78℃;	A 5 % Chromat. B 29 % Chromat. C 66 % Chromat.

3-cyclopropylmethoxy-3-chlorodiaziridine (122651-94-9) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

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 (594-11-6) + chlorine (7782-50-5) → 3-butenyl chloride (927-73-1) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at -20℃;
at 50℃;

thionyl chloride (7719-09-7) + Cyclopropylmethanol (2516-33-8) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

pyridine (110-86-1) + thionyl chloride (7719-09-7) + Cyclopropylmethanol (2516-33-8) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

thionyl chloride (7719-09-7) + cyclobutanol (2919-23-5) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

pyridine (110-86-1) + thionyl chloride (7719-09-7) + cyclobutanol (2919-23-5) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

ethanol (64-17-5) + cyclopropylmethoxychlorocarbene → chlorocyclobutane (1120-57-6) + cyclobutyl ethyl ether (70097-82-4) + cyclopropylcarbinyl ethyl ether (70097-81-3) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at 25℃; Product distribution; Further Variations:; Solvents;

ethanol (64-17-5) + cyclobutoxychlorocarbene (364612-99-7) → chlorocyclobutane (1120-57-6) + cyclobutyl ethyl ether (70097-82-4) + cyclopropylcarbinyl ethyl ether (70097-81-3) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at 25℃; Product distribution; Further Variations:; Solvents;

cyclopropylmethoxychlorocarbene → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

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 (364612-99-7) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

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 (122651-94-9) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + 1,4-dichlorobutane (110-56-5) + chloro(cyclopropyl)methane (5911-08-0)

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 (225668-16-6) + chloro(cyclopropyl)methane (5911-08-0) → 5,6-bis(3-fluoro-4-methoxyphenyl)-2-cyclopropylmethyl-2H-pyridazin-3-one

Conditions	Yield
	100%

1-(4-hydroxy-2,6-dimethylphenyl)ethanone (91060-92-3) + chloro(cyclopropyl)methane (5911-08-0) → 1-(4-(cyclopropylmethoxy)-2,6-dimethylphenyl)ethanone (1439935-91-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	99%

4-cyanophenol (767-00-0) + chloro(cyclopropyl)methane → 4-(cyclopropylmethoxy)benzonitrile

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 (22246-16-8) + chloro(cyclopropyl)methane (5911-08-0) → 1-(cyclopropylmethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

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 (225668-09-7) + chloro(cyclopropyl)methane (5911-08-0) → 2-cyclopropylmethyl-5-(3-fluoro-4-methoxyphenyl)-6-(4-methoxyphenyl)-2H-pyridazin-3-one

Conditions	Yield
	93.8%

N-norcodeine hydrochloride (14648-14-7) + chloro(cyclopropyl)methane (5911-08-0) → 17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-3-methoxymorphinan-6α-ol (77794-51-5)

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 (225668-02-0) + chloro(cyclopropyl)methane (5911-08-0) → 6-(3-fluoro-4-methoxyphenyl)-2-isobutyl-5-(4-methoxyphenyl)-2H-pyridazin-3-one

Conditions	Yield
	93%

11-oxo(10H)-pyrrolo<2,1-c><1,2,5>benzothiadiazepine 5,5-dioxide (142529-02-0) + chloro(cyclopropyl)methane (5911-08-0) → 9-Cyclopropylmethyl-4,4-dioxo-4,9-dihydro-4λ6-thia-3a,9-diaza-benzo[f]azulen-10-one

Conditions	Yield
With potassium carbonate; potassium iodide In acetone for 24h; Ambient temperature;	90%

phenylmagnesium bromide (100-58-3) + chloro(cyclopropyl)methane (5911-08-0) → benzylcyclopropane (1667-00-1)

Conditions	Yield
With 1-Phenylprop-1-yne; copper dichloride In tetrahydrofuran at 70℃; for 12h;	90%

chloro(cyclopropyl)methane (5911-08-0) → 6-bromo-2-(2-cyclopropanemethyl)isoquinolin-1(2H)-one (1070294-27-7)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 3h;	90%

chloro(cyclopropyl)methane (5911-08-0) + 5,6-bis(4-Methoxyphenyl)-4-ethoxy-carbonyl-2H-pyridazin-3-one (70768-88-6) → 5,6-bis(4-methoxyphenyl)-2-cyclopropylmethyl-4-ethoxycarbonyl-2H-pyridazin-3-one (288586-95-8)

Conditions	Yield
	89.1%

(1r,4r)-4-(tritylamino)cyclohexanol + chloro(cyclopropyl)methane (5911-08-0) → C29H33NO

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 (5911-08-0) + (-)-3,14β-dimethoxy-4,5-α-epoxy-5β-methylmorphinan-6-one hydrochloride → (-)-17-(cyclopropylmethyl)-3,14β-dimethoxy-4,5-α-epoxy-5β-methylmorphinan-6-one (159022-20-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 22h;	86%

chloro(cyclopropyl)methane (5911-08-0) + AR-M390 (209808-01-5) → 4-[(1-cyclopropylmethyl-piperidin-4-ylidene)-phenyl-methyl]-N,N-diethyl-benzamide

Conditions	Yield
With potassium carbonate In acetonitrile at 25℃; for 0.5h;	86%

Cyclopropylmethanol (2516-33-8) → chloro(cyclopropyl)methane (5911-08-0)

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 (56-23-5) + tri(cyclopropylmethyl)phosphite (112057-32-6) → 3-butenyl chloride (927-73-1) + Phosphoric acid tricyclopropylmethyl ester (27301-78-6) + Trichloromethyl-phosphonic acid dicyclopropylmethyl ester (112142-26-4) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
In toluene at 80℃; Further byproducts given;	A 16% B 2% C 80% D 64%

Cyclopropylmethanol (2516-33-8) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
	A 15% B 18% C 80%

cyclopropylmethyl (2154-76-9) → 3-butenyl chloride (927-73-1) + 1,3-dichlorobutane (1190-22-3) + 1,2,4-trichlorobutane (1790-22-3) + chloro(cyclopropyl)methane (5911-08-0)

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 (594-11-6) → 3-butenyl chloride (927-73-1) + 1,3-dichlorobutane (1190-22-3) + 1,2,4-trichlorobutane (1790-22-3) + chloro(cyclopropyl)methane (5911-08-0)

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%

Cyclopropylmethanol (2516-33-8) + cyclobutanol (2919-23-5) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
With phosphorus pentachloride
With hydrogenchloride

methylcyclopropane (594-11-6) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
With chlorine Irradiation;
With chlorine at -196.1℃; Quantum yield; Irradiation; var. magnetic field;

chlorocyclobutane (1120-57-6) + potassium acetate (127-08-2) + acetic acid (64-19-7) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at 100℃; Rate constant; Solvolyse und Isomerisierung;

diazomethane (186581-53-3, 908094-01-9) + 3-chloroprop-1-ene (107-05-1) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
Cu catalyst

3,4-dichlorobut-1-ene (310447-99-5, 310448-01-2) → chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
(i) 9-bora-bicyclo<3.3.1>nonane, THF, (ii) aq. NaOH; Multistep reaction;

tetrachloromethane (56-23-5) + tri(cyclopropylmethyl)phosphite (112057-32-6) → 3-butenyl chloride (927-73-1) + Dicyclopropylcarbinyl-phosphonat (6554-31-0) + Phosphoric acid tricyclopropylmethyl ester (27301-78-6) + Trichloromethyl-phosphonic acid dicyclopropylmethyl ester (112142-26-4) + chloro(cyclopropyl)methane (5911-08-0)

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 (64-17-5) + 3-cyclopropylmethoxy-3-chlorodiaziridine (122651-94-9) → 3-butenyl chloride (927-73-1) + allylcarbinyl ethyl ether (44611-46-3) + chlorocyclobutane (1120-57-6) + cyclobutyl ethyl ether (70097-82-4) + cyclopropylcarbinyl ethyl ether (70097-81-3) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
In ethanol; acetonitrile at 25℃; Thermodynamic data; Kinetics; Product distribution; Ea, effect of solvents;

ethanol (64-17-5) + 3-cyclopropylmethoxy-3-chlorodiaziridine (122651-94-9) → allylcarbinyl ethyl ether (44611-46-3) + cyclobutyl ethyl ether (70097-82-4) + cyclopropylcarbinyl ethyl ether (70097-81-3) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at 25℃; Further byproducts given;	A 1 % Chromat. B 22 % Chromat. C 28 % Chromat. D 42 % Chromat.

ethanol (64-17-5) + 3-cyclopropylmethoxy-3-chlorodiaziridine (122651-94-9) → chlorocyclobutane (1120-57-6) + cyclobutyl ethyl ether (70097-82-4) + cyclopropylcarbinyl ethyl ether (70097-81-3) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
at 25℃; Further byproducts given;	A 5 % Chromat. B 22 % Chromat. C 28 % Chromat. D 42 % Chromat.

bicyclo[1.1.0]butane (157-33-5) → chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

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 (75637-38-6) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
With triphenyl phosphite In dichloromethane at -78℃;	A 1.5 % Chromat. B 8.5 % Chromat. C 90 % Chromat.

cyclobutyl hypochlorite (75637-39-7) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

Conditions	Yield
With triphenyl phosphite In dichloromethane at -78℃;	A 5 % Chromat. B 29 % Chromat. C 66 % Chromat.

3-cyclopropylmethoxy-3-chlorodiaziridine (122651-94-9) → 3-butenyl chloride (927-73-1) + chlorocyclobutane (1120-57-6) + chloro(cyclopropyl)methane (5911-08-0)

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.

Upstream product

• 2516-33-8 Cyclopropylmethanol 
• 2919-23-5 cyclobutanol 
• 594-11-6 methylcyclopropane 
• 1120-57-6 chlorocyclobutane 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 186581-53-3 diazomethane 
• 107-05-1 3-chloroprop-1-ene 
• 310447-99-5 3,4-dichlorobut-1-ene 
• 56-23-5 tetrachloromethane 
• 112057-32-6 tri(cyclopropylmethyl)phosphite 
• 64-17-5 ethanol 
• 122651-94-9 3-cyclopropylmethoxy-3-chlorodiaziridine 
• 157-33-5 bicyclo[1.1.0]butane 

Downstream Products

• 927-73-1 3-butenyl chloride 
• 1120-57-6 chlorocyclobutane 
• 36982-54-4 (acetoxymethyl)cyclopropane 
• 57297-73-1 cyclobutyl acetate 
• 594-11-6 methylcyclopropane 
• 58862-95-6 <(N,N-dimethylamino)methyl>cyclopropane 
• 74339-17-6 1-anilino-2-cyclopropyl-1,1-diphenylethane 
• 97280-20-1 diethyl N-<4-<(cyclopropylmethyl)amino>benzoyl>-L-glutamate 
• 97280-16-5 diethyl N-<4-benzoyl>-L-glutamate 
• 118111-54-9 cyprodime 
• 112246-80-7 (-)-17-Cyclopropylmethylmorphinan-6-one 
• 131575-18-3 3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one 
• 79257-06-0 1-cyclopropylmethyl-2,3-dihydro-2-phenylspiro 
• 79242-40-3 C₂₂H₂₄ClNO 

Relevant articles and documents

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Method for synthesizing cylopropylmethyl chloride by using cyclopropanemethanol

The invention relates to the field of organic synthesis and discloses a method for synthesizing cylopropylmethyl chloride by using cyclopropanemethanol. The method comprises the following steps: (A) dissolving cyanuric chloride into a solvent A to obtain a solution; (B) dropwise adding the cyclopropanemethanol into the prepared solution for reacting; (C) adding a reaction solution finished the reaction into an alkali solution for quenching; (D) extracting a target product by using a solvent B, drying and rectifying to obtain a product. According to the method, the cyclopropanemethanol and the cyanuric chloride are used as raw materials, and are easy to obtain, low in cost and less in pollution; in addition, the method has the advantages of mild reaction conditions, simple post treatment and suitability for industrial production.

Ni-catalyzed cascade cyclization-kumada alkyl-alkyl cross-coupling

Suggesting novel disconnections: A powerful Ni-catalyzed cascade reaction involving cyclization followed by cross-coupling allows the formation of up to three alkyl-alkyl bonds in a single operation by using alkene-containing alkyl iodides and Grignard reagents (see scheme; acac=acetylacetonate; TMEDA=N,N′,N′-tetramethyl ethylenediamine). Mechanistic experimental and computational studies suggest a NiI-NiII-Ni III catalytic cycle and the intermediacy of radicals. Copyright

Rearrangements concerted with fragmentation of cyclopropylmethoxychlorocarbene and cyclobutoxychlorocarbene in hydrocarbon solvents and Ar matrices

Fragmentations of cyclopropylmethoxychlorocarbene (6) and cyclobutoxychlorocarbene (10) lead to rearrangments that afford mixtures of cyclopropylmethyl chloride (7), cyclobutyl chloride (8), and 3-butenyl chloride (9). Isotopic substitution studies show that these rearrangments are accompanied by partial exchange of the methylene groups within 6 and 10. Surprisingly, these processes that are typical of carbocations persist in hydrocarbon solvents such as pentane and cyclohexane-d12. Quantum chemical calculations reveal that the cis-conformers of the incipient oxychlorocarbenes C 4H7OCCl decay to C4H7Cl + CO via transient hydrogen bonded C4H7 σ+...Clσ- complexes which possess significant ion pair character, even in the gas phase or in nonpolar solvents. In contrast to benzyloxychlorocarbene, no free radicals are formed upon generation or photolysis of 6 or 10 in Ar matrixes, although acid chlorides (the recombination products of these radical pairs) are observed. The IR spectra obtained in these experiments show the presence of several conformers of the two C4H7OCCl.