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4606-07-9

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4606-07-9 Usage

Chemical Properties

clear pale yellow liquid

Uses

Different sources of media describe the Uses of 4606-07-9 differently. You can refer to the following data:
1. Ethyl cyclopropanecarboxylate is a reagent used in the addition of cyclopropane.
2. Ethyl cyclopropanecarboxylate is a reagent used in the addition of cyclopropane. It acts as annulation reagent for the conversion of aromatics to 2-methylindanones under Friedel-Crafts conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 4606-07-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,6,0 and 6 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4606-07:
(6*4)+(5*6)+(4*0)+(3*6)+(2*0)+(1*7)=79
79 % 10 = 9
So 4606-07-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O2/c1-2-8-6(7)5-3-4-5/h5H,2-4H2,1H3

4606-07-9 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (B24870)  Ethyl cyclopropanecarboxylate, 98%   

  • 4606-07-9

  • 25g

  • 309.0CNY

  • Detail
  • Alfa Aesar

  • (B24870)  Ethyl cyclopropanecarboxylate, 98%   

  • 4606-07-9

  • 100g

  • 793.0CNY

  • Detail
  • Alfa Aesar

  • (B24870)  Ethyl cyclopropanecarboxylate, 98%   

  • 4606-07-9

  • 500g

  • 3385.0CNY

  • Detail

4606-07-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl Cyclopropanecarboxylate

1.2 Other means of identification

Product number -
Other names Cyclopropanecarboxylic acid Ethyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4606-07-9 SDS

4606-07-9Synthetic route

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With sulfuric acid In ethanol98%
ethyl α,γ-dichlorobutyrate
77100-87-9

ethyl α,γ-dichlorobutyrate

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With tetraethylammonium tosylate In dimethyl sulfoxide electrolysis;82%
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

A

ethyl 4-hydroxybutanoate
999-10-0

ethyl 4-hydroxybutanoate

B

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With oxygen; tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; electroreduction at -1.1 V;A 10%
B 68%
n-octyne
629-05-0

n-octyne

ethyl 4-iodobutyrate
7425-53-8

ethyl 4-iodobutyrate

A

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

B

C20H32O

C20H32O

Conditions
ConditionsYield
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran at 20℃;
Stage #2: ethyl 4-iodobutyrate In tetrahydrofuran at 20℃;
A 9%
B 65%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With sodium tert-pentoxide; benzene
With sodium tert-pentoxide In benzene
With N-(diphenylmethylidene)phenylamine at -78℃;
With copper(I) oxide; Cyclohexyl isocyanide
With potassium hydroxide; tetrabutylammomium bromide In toluene at 40℃; for 2h;91 % Chromat.
3-Bromo-2-bromomethyl-propionic acid ethyl ester
58539-11-0

3-Bromo-2-bromomethyl-propionic acid ethyl ester

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With ethanol; zinc
ethanol
64-17-5

ethanol

cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

ethyl 2-oxocyclohexane carboxylate
1655-07-8

ethyl 2-oxocyclohexane carboxylate

A

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

B

ethyl 1-(3-(ethoxycarbonyl)propyl)-2-oxocyclohexanecarboxylate
124355-49-3

ethyl 1-(3-(ethoxycarbonyl)propyl)-2-oxocyclohexanecarboxylate

Conditions
ConditionsYield
With sodium ethanolate
ethanol
64-17-5

ethanol

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With sulfuric acid
With ε-caprolactam methyl sulfonate at 30℃; for 8h; chemoselective reaction;87 %Chromat.
With quaternary ammonium salt functionalized methoxypolyethylene glycols-supported phosphotungstic acid catalyst at 50℃; for 3h;
With thionyl chloride Reflux;
With sulfuric acid for 12h; Inert atmosphere; Reflux;
Tosylat von 4-Aethoxy-butin-(3)-ol
19999-37-2

Tosylat von 4-Aethoxy-butin-(3)-ol

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With pyridine In water; acetone at 55℃; for 120h;
oxirane
75-21-8

oxirane

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With 1.) base Multistep reaction;
2-bromocyclobutanone
1192-01-4

2-bromocyclobutanone

sodium ethanolate
141-52-6

sodium ethanolate

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

ethyl 2,4-dibromobutyrate
36847-51-5

ethyl 2,4-dibromobutyrate

A

4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

B

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

C

butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; Product distribution; Mechanism; electrolysis; I*, napp; various conc. of the ester; in the presence and in the absence of 3,4-xylenol;
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

Boc-Tyr-OH
3978-80-1

Boc-Tyr-OH

A

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

B

ethyl 4-<4'-<<2-<(tert-butoxycarbonyl)amino>-2-carboxy>ethyl>phenoxy>butanoate
171858-32-5

ethyl 4-<4'-<<2-<(tert-butoxycarbonyl)amino>-2-carboxy>ethyl>phenoxy>butanoate

Conditions
ConditionsYield
With sodium hydride 1.) THF, RT, 5 min, 2.) THF, reflux, 21 h; Yield given. Multistep reaction;
1,1-cyclopropanedicarboxylic acid monoethyl ester
3697-66-3

1,1-cyclopropanedicarboxylic acid monoethyl ester

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With 1-hydroxy-2(1H)-pyridinethione; dicyclohexyl-carbodiimide 1.) CHCl3, room temperature, 6 h, 2.) CHCl3, room temperature, irradiation; Yield given. Multistep reaction;
ethyl 1-chlorocarbonylcyclopropanecarboxylate
3697-67-4

ethyl 1-chlorocarbonylcyclopropanecarboxylate

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With 2-mercaptopyridine-1-oxide sodium salt 2.) room temperature, irradiation; Multistep reaction;
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

KOH

KOH

pumice stone

pumice stone

A

4-butanolide
96-48-0

4-butanolide

B

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

C

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
at 180℃;
diethyl sulfate
64-67-5

diethyl sulfate

potassium-salt of/the/ cyclopropanecarboxylic acid

potassium-salt of/the/ cyclopropanecarboxylic acid

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

ethyl iodide
75-03-6

ethyl iodide

silver salt of/the/ cyclopropane-carboxylic acid

silver salt of/the/ cyclopropane-carboxylic acid

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

A

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

B

cyclopropanecarboxylic acid , γ-butyrolactone

cyclopropanecarboxylic acid , γ-butyrolactone

Conditions
ConditionsYield
With potassium hydroxide; pumice stone at 180℃;
ethanol
64-17-5

ethanol

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With sulfuric acid
diethyl cyclopropane-1,1-dicarboxylate
1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

ultra-violet light

ultra-violet light

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 58 percent / magnesium iodide / toluene / 8 h / Heating
2: 1.) 1-hydroxy-pyridine-2-thione, dicyclohexyl-carbodiimide / 1.) CHCl3, room temperature, 6 h, 2.) CHCl3, room temperature, irradiation
View Scheme
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

isobutene
115-11-7

isobutene

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With phenylhydrazine In toluene
In ethyl acetate; toluene
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethene
74-85-1

ethene

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 40℃; under 6000.6 Torr; for 14h; Catalytic behavior; Temperature; Inert atmosphere; Schlenk technique;70 %Chromat.
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethene
74-85-1

ethene

A

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

B

diethyl Fumarate
623-91-6

diethyl Fumarate

C

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
ConditionsYield
With tetrakis(trifluoroacetato)rhodium(II) In dichloromethane at 20℃; under 6000.6 Torr; for 14h; Reagent/catalyst; Inert atmosphere; Schlenk technique;A 41 %Chromat.
B n/a
C n/a
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethene
74-85-1

ethene

A

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

(E)-Cyclopropan-1,2,3-tricarbonsaeuretriethylester
729-87-3, 13950-16-8

(E)-Cyclopropan-1,2,3-tricarbonsaeuretriethylester

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 20℃; under 1500.15 Torr; for 14h; Catalytic behavior; Pressure; Inert atmosphere; Schlenk technique;A 39 %Chromat.
B 35 %Chromat.
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

cyclopropanecarbohydrazide
6952-93-8

cyclopropanecarbohydrazide

Conditions
ConditionsYield
With hydrazine hydrate at 120℃; for 16h;100%
With hydrazine hydrate
With hydrazine In ethanol for 3h; Heating;
With hydrazine hydrate at 80℃;
With hydrazine hydrate In ethanol at 80℃; for 18h; Sealed tube;
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

2-((2-methoxyphenyl)thio)acetonitrile
79506-64-2

2-((2-methoxyphenyl)thio)acetonitrile

5-cyclopropyl-4-((2-methoxyphenyl)thio)oxazole

5-cyclopropyl-4-((2-methoxyphenyl)thio)oxazole

Conditions
ConditionsYield
Stage #1: 2-((2-methoxyphenyl)thio)acetonitrile With n-butyllithium In hexane at -78℃;
Stage #2: ethyl cyclopropylcarboxylate In hexane at -78 - 20℃;
100%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

dimethyl aluminum selenide
67132-62-1

dimethyl aluminum selenide

Cyclopropanecarboselenoic acid Se-methyl ester
67132-66-5

Cyclopropanecarboselenoic acid Se-methyl ester

Conditions
ConditionsYield
In dichloromethane; toluene 1.) 0 deg C, 2.) up to RT;96%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

benzene
71-43-2

benzene

2,3-dihydro-2-methyl-1H-inden-1-one
17496-14-9

2,3-dihydro-2-methyl-1H-inden-1-one

Conditions
ConditionsYield
aluminium trichloride for 16h; Heating;93%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

methyl iodide
74-88-4

methyl iodide

2-cyclopropyl-2-propanol
930-39-2

2-cyclopropyl-2-propanol

Conditions
ConditionsYield
With magnesium In diethyl ether 1) room temp., 30 min, 2) reflux, 1 h;92.7%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

acetonitrile
75-05-8

acetonitrile

3-cyclopropyl-3-oxo-propionitrile
118431-88-2

3-cyclopropyl-3-oxo-propionitrile

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 16h;90%
With potassium tert-butylate; isopropyl alcohol In 2-methyltetrahydrofuran at 20℃; for 2h; Solvent; Time; Inert atmosphere;48%
With sodium hydride In tetrahydrofuran for 15h; Heating / reflux;
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

(2-fluorophenyl)acetic acid
451-82-1

(2-fluorophenyl)acetic acid

1-cyclopropyl-2-(2-fluorophenyl)ethanone
150322-73-9

1-cyclopropyl-2-(2-fluorophenyl)ethanone

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide; toluene at 95 - 110℃; for 1.5h; Large scale;88%
Stage #1: (2-fluorophenyl)acetic acid With magnesium; isopropyl bromide In tetrahydrofuran; toluene at 15 - 65℃;
Stage #2: ethyl cyclopropylcarboxylate In tetrahydrofuran; toluene at 5 - 65℃;
diethyl ether
60-29-7

diethyl ether

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

(triethoxymethyl)cyclopropane

(triethoxymethyl)cyclopropane

Conditions
ConditionsYield
With boron trifluoride In Hexadecane at 110℃; for 18h; Autoclave;88%
bromobenzene
108-86-1

bromobenzene

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

cyclopropyl diphenyl carbinol
5785-66-0

cyclopropyl diphenyl carbinol

Conditions
ConditionsYield
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; Barbier Coupling Reaction; chemoselective reaction;84%
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; chemoselective reaction;84%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

N,N-bis(2-bromoallyl)-4-methylaniline
13633-36-8

N,N-bis(2-bromoallyl)-4-methylaniline

3-(2-cyclopropyl-2-oxoethyl)-2,5-dihydro-4-methyl-1-(4-methylphenyl)-1H-pyrrole
545435-10-7

3-(2-cyclopropyl-2-oxoethyl)-2,5-dihydro-4-methyl-1-(4-methylphenyl)-1H-pyrrole

Conditions
ConditionsYield
Stage #1: N,N-bis(2-bromoallyl)-4-methylaniline With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; for 1.5h;
Stage #2: ethyl cyclopropylcarboxylate In diethyl ether; pentane at -78℃; for 1h;
82%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

aniline
62-53-3

aniline

N-phenylcyclopropanecarboxamide
2759-52-6

N-phenylcyclopropanecarboxamide

Conditions
ConditionsYield
With chromium chloride; magnesium In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;82%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

N,N-bis(2-bromoallyl)-4-methylaniline
13633-36-8

N,N-bis(2-bromoallyl)-4-methylaniline

5-cyclopropyl-1,2,3,4,5,6-hexahydro-2-(4-methylphenyl)cyclopenta[c]pyrrol-5-ol
545435-11-8

5-cyclopropyl-1,2,3,4,5,6-hexahydro-2-(4-methylphenyl)cyclopenta[c]pyrrol-5-ol

Conditions
ConditionsYield
Stage #1: N,N-bis(2-bromoallyl)-4-methylaniline With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; for 1.5h;
Stage #2: ethyl cyclopropylcarboxylate In diethyl ether; pentane at -78 - 20℃;
80%
para-bromotoluene
106-38-7

para-bromotoluene

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

(cyclopropyl)(di-p-tolyl)methanol
7035-46-3

(cyclopropyl)(di-p-tolyl)methanol

Conditions
ConditionsYield
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; Barbier Coupling Reaction; chemoselective reaction;78%
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; chemoselective reaction;78%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

(trimethylsilyl)methylmagnesium chloride
13170-43-9

(trimethylsilyl)methylmagnesium chloride

2-cyclopropyl-2-propenyltrimethylsilane
144729-87-3

2-cyclopropyl-2-propenyltrimethylsilane

Conditions
ConditionsYield
With cesium chloride; silica gel73%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

carbon monoxide
201230-82-2

carbon monoxide

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

1-Cyclopropyl-hexane-1,2-dione
136201-68-8

1-Cyclopropyl-hexane-1,2-dione

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; hexane; pentane a) -110 deg C, 2 h, b) to r.t.;67%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

toluene
108-88-3

toluene

2,6-dimethylindan-1-one
66309-83-9

2,6-dimethylindan-1-one

Conditions
ConditionsYield
aluminium trichloride In toluene Heating;67%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

2,2'-(2-(2,4-dimethylphenyl)ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2,2'-(2-(2,4-dimethylphenyl)ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

methyl iodide
74-88-4

methyl iodide

1-cyclopropyl-3-(2,4-dimethylphenyl)-2,2-dimethylpropan-1-one

1-cyclopropyl-3-(2,4-dimethylphenyl)-2,2-dimethylpropan-1-one

Conditions
ConditionsYield
Stage #1: 2,2'-(2-(2,4-dimethylphenyl)ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: ethyl cyclopropylcarboxylate In tetrahydrofuran; hexane at 50℃; for 0.25h; Inert atmosphere;
Stage #3: methyl iodide In tetrahydrofuran; hexane at 20℃; for 0.25h; Inert atmosphere; regioselective reaction;
65%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

1-benzyloxy-2-iodobenzene
142523-69-1

1-benzyloxy-2-iodobenzene

3-cyclopropyl-2-phenylbenzo[b]furan

3-cyclopropyl-2-phenylbenzo[b]furan

Conditions
ConditionsYield
Stage #1: 1-benzyloxy-2-iodobenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -25℃;
Stage #2: ethyl cyclopropylcarboxylate In tetrahydrofuran; pentane at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane at 20℃;
64%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

cyclopropane carbohydroxamic acid
5687-86-5

cyclopropane carbohydroxamic acid

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride In ethanol for 8h; Ambient temperature;60%
With hydroxylamine; sodium methylate
With potassium hydroxide; hydroxylamine hydrochloride In methanol
carbon monoxide
201230-82-2

carbon monoxide

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

tert.-butyl lithium
594-19-4

tert.-butyl lithium

A

1-cyclohexyl-2,2-dimethyl-1-propanone
15963-60-7

1-cyclohexyl-2,2-dimethyl-1-propanone

B

Cyclopropyl-1-dimethyl-3,3-butan-dion-1,2
34650-62-9

Cyclopropyl-1-dimethyl-3,3-butan-dion-1,2

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; hexane; pentane a) -110 deg C, 2 h, b) to r.t.;A 3%
B 60%
2-chloro-4-methylpyrimidine
13036-57-2

2-chloro-4-methylpyrimidine

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

C9H9ClN2O

C9H9ClN2O

Conditions
ConditionsYield
Stage #1: 2-chloro-4-methylpyrimidine With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h;
Stage #2: ethyl cyclopropylcarboxylate In tetrahydrofuran at -78℃; for 5h;
46%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

1-(benzyloxy)-2-bromo-4-methylbenzene
2830-53-7

1-(benzyloxy)-2-bromo-4-methylbenzene

3-cyclopropyl-5-methyl-2-phenylbenzo[b]furan

3-cyclopropyl-5-methyl-2-phenylbenzo[b]furan

Conditions
ConditionsYield
Stage #1: 1-(benzyloxy)-2-bromo-4-methylbenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -25℃;
Stage #2: ethyl cyclopropylcarboxylate In tetrahydrofuran; pentane at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane at 20℃;
45%
ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

(2-(4-bromophenyl)cyclopropane-1,1-diyl)dibenzene
96010-06-9

(2-(4-bromophenyl)cyclopropane-1,1-diyl)dibenzene

cyclopropyl[bis-(4-(2,2-diphenylcyclopropyl)phenyl)]methanol
1251909-11-1

cyclopropyl[bis-(4-(2,2-diphenylcyclopropyl)phenyl)]methanol

Conditions
ConditionsYield
Stage #1: (2-(4-bromophenyl)cyclopropane-1,1-diyl)dibenzene With magnesium In tetrahydrofuran
Stage #2: ethyl cyclopropylcarboxylate In tetrahydrofuran
43%
5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate rhodium(II)
121393-39-3

5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate rhodium(II)

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

C62H63N4O2Rh

C62H63N4O2Rh

Conditions
ConditionsYield
Stage #1: 5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate rhodium(II) With triphenylphosphine In benzene at 25℃; for 0.166667h;
Stage #2: ethyl cyclopropylcarboxylate In benzene at 25℃; for 96h; Inert atmosphere; Darkness; regioselective reaction;
38%
allylbenzene
300-57-2

allylbenzene

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

2-benzylbi(cyclopropan)-1-ol

2-benzylbi(cyclopropan)-1-ol

Conditions
ConditionsYield
With triisopropoxytitanium(IV) chloride; cyclohexylmagnesiumchloride In tetrahydrofuran; diethyl ether at 20℃; for 2h; Inert atmosphere;33%

4606-07-9Relevant articles and documents

Intermolecular Electrophilic Bromoesterification and Bromoetherification of Unactivated Cyclopropanes

Leung, Vincent Ming-Yau,Gieuw, Matthew H.,Ke, Zhihai,Yeung, Ying-Yeung

supporting information, p. 2039 - 2044 (2020/04/20)

1,3-difunctionalization of cyclopropane is an useful organic transformation. The corresponding 1,3-difunctionalized products are synthetic synthons and building blocks in many organic syntheses. Many existing ring-opening difunctionalization methodologies rely primarily on the use of donor?acceptor cyclopropanes, while the difunctionalization of unactivated cyclopropanes is less exploited. In this research, 1,3-bromoesterification and 1,3-bromoetherification of unactivated cyclopropanes were successfully achieved using N-bromosuccinimide as the brominating agent with high yields and regioselectivity. (Figure presented.).

Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes

Chanda, Tanmoy,Chowdhury, Sushobhan,Anand, Namrata,Koley, Suvajit,Gupta, Ashutosh,Singh, Maya Shankar

supporting information, p. 981 - 985 (2015/03/04)

First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spirocyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol.

Cross-coupling of nonactivated alkyl halides with alkynyl grignard reagents: A nickel pincer complex as the catalyst

Vechorkin, Oleg,Godinat, Aurélien,Scopelliti, Rosario,Hu, Xile

supporting information; experimental part, p. 11777 - 11781 (2012/01/19)

In a pinch: The nickel pincer complex 1 catalyzes the cross-coupling of the title compounds with remarkable substrate scope and functional group tolerance. A nickel/alkynyl species was isolated and shown to be catalytically competent. THF=tetrahydrofuran, O-TMEDA=bis[2-(N,N-dimethylaminoethyl)] ether. Copyright

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