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Synthetic route

Cyclopentane
287-92-3

Cyclopentane

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Conditions
ConditionsYield
With potassium chloride; tetrabutyl-ammonium chloride; acetic acid In water at 20℃; for 6.5h; Reagent/catalyst;96%
With sodium hypochlorite In water; acetone at 20℃; for 2h; Inert atmosphere;95%
With hydrogenchloride; potassium chloride; tetrabutyl-ammonium chloride In water at 20℃; Irradiation; Green chemistry;94%
cyclopentyl o-(N-methylcarbamoyl)phenyl sulphoxide

cyclopentyl o-(N-methylcarbamoyl)phenyl sulphoxide

A

2-methyl-1,2-benzisothiazole-3(2H)-one
2527-66-4

2-methyl-1,2-benzisothiazole-3(2H)-one

B

cyclopentyl chloride
930-28-9

cyclopentyl chloride

C

2-chlorocyclopentyl o-(N-methylcarbamoyl)phenyl sulphide

2-chlorocyclopentyl o-(N-methylcarbamoyl)phenyl sulphide

Conditions
ConditionsYield
With thionyl chloride In dichloromethane for 1h; Heating;A 53%
B 83%
C 10%
Cyclopentanol
96-41-3

Cyclopentanol

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

cyclopentene
142-29-0

cyclopentene

Conditions
ConditionsYield
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane 1.) 0 deg C; 2.) rt., 3h;A 80%
B n/a
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane 1.) 0 deg C; 2.)rt., 3h;
With bismuth(III) chloride In tetrachloromethane for 1.5h; Heating;
cyclopentene
142-29-0

cyclopentene

A

Cyclopentanol
96-41-3

Cyclopentanol

B

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Conditions
ConditionsYield
With tetrachloromethane; copper(II) choride dihydrate; chromium(III) acetylacetonate; water at 130℃; for 12h; Sealed tube;A 80%
B 20%
cyclopentanone
120-92-3

cyclopentanone

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Conditions
ConditionsYield
With dichloromethylsilane; iron(III) chloride In 1,2-dimethoxyethane for 6h; Heating;75%
Cyclopentanol
96-41-3

Cyclopentanol

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Conditions
ConditionsYield
With tertiary butyl chloride; n-pentylmethylimidazolium bromide at 60℃; for 3.75h;72%
With pyridine; p-toluenesulfonyl chloride at 100℃;40%
With phosphorus trichloride
cyclopentyl chloroformate
50715-28-1

cyclopentyl chloroformate

trifluoroborane diethyl ether
109-63-7

trifluoroborane diethyl ether

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

cyclopentene
142-29-0

cyclopentene

cyclopentyl chloroformate
50715-28-1

cyclopentyl chloroformate

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Conditions
ConditionsYield
With boron fluoride ether; pentane
With hexane; boron fluoride ether
tetrachloromethane
56-23-5

tetrachloromethane

cyclopentene
142-29-0

cyclopentene

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

1,2-dichlorocyclopentane
14916-75-7

1,2-dichlorocyclopentane

C

1-chloro-2-(trichloromethyl)cyclopentane
7582-02-7

1-chloro-2-(trichloromethyl)cyclopentane

D

3,3'-bicyclopentenyl
2690-18-8

3,3'-bicyclopentenyl

Conditions
ConditionsYield
Irradiation; Further byproducts given;
tetrachloromethane
56-23-5

tetrachloromethane

cyclopentene
142-29-0

cyclopentene

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

1,2-dichlorocyclopentane
14916-75-7

1,2-dichlorocyclopentane

C

Trichlormethyl-cyclopentan
7582-01-6

Trichlormethyl-cyclopentan

Conditions
ConditionsYield
Irradiation; Further byproducts given;
dichloromethane
75-09-2

dichloromethane

cyclopentene
142-29-0

cyclopentene

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

chloromethylcyclopentane
13988-39-1

chloromethylcyclopentane

C

3,3'-bicyclopentenyl
2690-18-8

3,3'-bicyclopentenyl

Conditions
ConditionsYield
(radiolysis);
cyclopentene
142-29-0

cyclopentene

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

1,2-dichlorocyclopentane
14916-75-7

1,2-dichlorocyclopentane

C

1-chloro-2-(trichloromethyl)cyclopentane
7582-02-7

1-chloro-2-(trichloromethyl)cyclopentane

Conditions
ConditionsYield
With tetrachloromethane Irradiation; Further byproducts given;
tetrachloromethane
56-23-5

tetrachloromethane

di-tert-butyl peroxide
110-05-4

di-tert-butyl peroxide

Cyclopentane
287-92-3

Cyclopentane

A

chloroform
67-66-3

chloroform

B

hexachloroethane
67-72-1

hexachloroethane

C

cyclopentyl chloride
930-28-9

cyclopentyl chloride

D

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
Product distribution; Irradiation;
cyclopentyldiphenylbismutane
96449-49-9

cyclopentyldiphenylbismutane

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With sulfuryl dichloride In dichloromethane -70 deg C to r.t.;A 43 % Chromat.
B 2 % Chromat.
Dichlorodifluoromethane
75-71-8

Dichlorodifluoromethane

cyclopentene
142-29-0

cyclopentene

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

(Chloro-difluoro-methyl)-cyclopentane
77116-58-6

(Chloro-difluoro-methyl)-cyclopentane

C

3-(Chloro-difluoro-methyl)-cyclopentene
77116-57-5

3-(Chloro-difluoro-methyl)-cyclopentene

(3aS,4R,7R,7aS)-5-(Chloro-difluoro-methyl)-octahydro-4,7-methano-indene
77116-59-7

(3aS,4R,7R,7aS)-5-(Chloro-difluoro-methyl)-octahydro-4,7-methano-indene

Conditions
ConditionsYield
at 200℃; Further byproducts given. Title compound not separated from byproducts;
cyclopentene
142-29-0

cyclopentene

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Conditions
ConditionsYield
With nitrogen trichloride; borane 1.) CH2Cl2, 0 deg C, 2.) CH2Cl2, 30 h, 25 deg C; Yield given. Multistep reaction;
Cyclopentane
287-92-3

Cyclopentane

chlorine
7782-50-5

chlorine

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Cyclopentane
287-92-3

Cyclopentane

chlorine
7782-50-5

chlorine

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Conditions
ConditionsYield
at 155℃;
at 155℃;
chloroform
67-66-3

chloroform

Cyclopentanol
96-41-3

Cyclopentanol

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

calcium carbonate

calcium carbonate

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

B

trans-1,2-dichloro-cyclopentane

trans-1,2-dichloro-cyclopentane

Cyclopentane
287-92-3

Cyclopentane

A

Cyclopentanol
96-41-3

Cyclopentanol

B

cyclopentyl chloride
930-28-9

cyclopentyl chloride

C

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With oxygen In acetonitrile at 13℃; under 760 Torr; Product distribution; Further Variations:; Reagents; Irradiation;
tetrachloromethane
56-23-5

tetrachloromethane

cyclopentene
142-29-0

cyclopentene

A

cyclopentyl chloride
930-28-9

cyclopentyl chloride

trans-1-chloro-2-(trichloromethyl)cyclopentane

trans-1-chloro-2-(trichloromethyl)cyclopentane

Conditions
ConditionsYield
With chromium(III) acetylacetonate; water at 140℃; for 6h; Autoclave;
C5H9ClO2S

C5H9ClO2S

cyclopentyl chloride
930-28-9

cyclopentyl chloride

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 0℃; for 1h; Inert atmosphere;
isovanillin
621-59-0

isovanillin

cyclopentyl chloride
930-28-9

cyclopentyl chloride

3-cyclopentyloxy-4-methoxybenzylaldehyde
67387-76-2

3-cyclopentyloxy-4-methoxybenzylaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 125℃; for 2h;100%
With potassium carbonate In N-methyl-acetamide
With potassium carbonate
cyclopentyl chloride
930-28-9

cyclopentyl chloride

tricyclo[8.2.1.02,9]trideca-5,11-diene-13-one

tricyclo[8.2.1.02,9]trideca-5,11-diene-13-one

anti-tricyclo[8.2.1.02,9]trideca-5,11-diene-13-ol

anti-tricyclo[8.2.1.02,9]trideca-5,11-diene-13-ol

Conditions
ConditionsYield
Stage #1: cyclopentyl chloride With magnesium In tetrahydrofuran at 50℃; for 1h;
Stage #2: tricyclo[8.2.1.02,9]trideca-5,11-diene-13-one In tetrahydrofuran at 40℃; for 0.166667h;
100%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

cyclopentylbenzene
700-88-9

cyclopentylbenzene

Conditions
ConditionsYield
With iron(III) chloride; N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran at 0 - 40℃; for 1.66667h;99%
With copper(l) iodide In 2-methyltetrahydrofuran; toluene at 80℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube;71%
With copper(l) iodide In 2-methyltetrahydrofuran; hexane at 80℃; for 14h; Schlenk technique; Inert atmosphere;70%
With iron(III) chloride; N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran at 0 - 40℃; for 1.66667h;
cyclopentyl chloride
930-28-9

cyclopentyl chloride

trimethylstannyl sodium
16643-09-7

trimethylstannyl sodium

Trimethylstannyl-cyclopentan
15095-84-8

Trimethylstannyl-cyclopentan

Conditions
ConditionsYield
In tetrahydrofuran 25°C in N2-atmosphere; various yields for various conditions;98%
In further solvent(s) byproducts: NaCl; under argon, equimolar amounts, at 0°C in tetraglyme; GLC;92%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

4-amino-5-bromo-2-chloropyrimidine
205672-25-9

4-amino-5-bromo-2-chloropyrimidine

5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
733039-20-8

5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine

Conditions
ConditionsYield
With triethylamine In methanol at 20℃;92.74%
With copper diacetate; sodium hydroxide In dichloromethane at 80℃; for 10h;77%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

N,N‐dimethyl-2‐{[5‐(4-tert-butoxycarbonylpiperazin‐1‐yl)pyridin‐2‐yl]amino}‐7H‐pyrrolo[2,3‐d]pyrimidine‐6‐ carboxamide

N,N‐dimethyl-2‐{[5‐(4-tert-butoxycarbonylpiperazin‐1‐yl)pyridin‐2‐yl]amino}‐7H‐pyrrolo[2,3‐d]pyrimidine‐6‐ carboxamide

N,N‐dimethyl‐7‐cyclopentyl‐2‐{[5‐(4-tert-butoxycarbonylpiperazin‐1‐yl)pyridin‐2‐yl]amino}‐7H‐pyrrolo[2,3‐d]pyrimidine‐6‐carboxamide
1374639-78-7

N,N‐dimethyl‐7‐cyclopentyl‐2‐{[5‐(4-tert-butoxycarbonylpiperazin‐1‐yl)pyridin‐2‐yl]amino}‐7H‐pyrrolo[2,3‐d]pyrimidine‐6‐carboxamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 55℃; for 5h;90.6%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

C19H23N7O2

C19H23N7O2

6-acetyl-8-cyclopentyl-5-methyl-2-[[5-(1-piperazinyl)-2-pyridinyl]amino]-5,6-dihydropyrido[2,3-d]pyrimidyl-7(8H)-one

6-acetyl-8-cyclopentyl-5-methyl-2-[[5-(1-piperazinyl)-2-pyridinyl]amino]-5,6-dihydropyrido[2,3-d]pyrimidyl-7(8H)-one

Conditions
ConditionsYield
With 1,10-Phenanthroline; potassium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 90℃; for 2h; Temperature; Reagent/catalyst;90.5%
2-cyclohex-1-enyl-pyridine
14159-55-8

2-cyclohex-1-enyl-pyridine

cyclopentyl chloride
930-28-9

cyclopentyl chloride

2-(2-cyclopentylcyclohex-1-en-1-yl)pyridine

2-(2-cyclopentylcyclohex-1-en-1-yl)pyridine

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; neopentylmagnesium bromide; cobalt(II) bromide; 1,3-diisopropyl-1H-benzo[d]imidazol-3-ium bromide In tetrahydrofuran at 0 - 20℃; for 12h; Schlenk technique;90%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

N-cyclopentyl-4-methoxybenzamide
346720-43-2

N-cyclopentyl-4-methoxybenzamide

Conditions
ConditionsYield
With zinc perchlorate In neat (no solvent) at 80℃; for 3h; Ritter Amidation;90%
With iron(II) chloride tetrahydrate In neat (no solvent) at 80℃; for 4h; Ritter Amidation;90%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

2-chloro-6-bromo-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

2-chloro-6-bromo-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

2-chloro-6-bromo-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

2-chloro-6-bromo-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

Conditions
ConditionsYield
With sodium acetate In ethanol at 20℃; for 7h;88%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

4,4,5,5-tetramethyl-2-(2-phenylhexan-2-yl)-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-(2-phenylhexan-2-yl)-1,3,2-dioxaborolane

(2-cyclopentylhexan-2-yl)benzene

(2-cyclopentylhexan-2-yl)benzene

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Sealed tube;88%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

(2,6-dibutylbenzo[1,2-b:5,4-b']difuran-3,5-diyl)bis((4-hydroxyphenyl)methanone)

(2,6-dibutylbenzo[1,2-b:5,4-b']difuran-3,5-diyl)bis((4-hydroxyphenyl)methanone)

(2,6-dibutylbenzo[1,2-b:5,4-b']difuran-3,5-diyl)bis((4-(cyclopentyloxy)phenyl)methylketone)

(2,6-dibutylbenzo[1,2-b:5,4-b']difuran-3,5-diyl)bis((4-(cyclopentyloxy)phenyl)methylketone)

Conditions
ConditionsYield
Stage #1: (2,6-dibutylbenzo[1,2-b:5,4-b']difuran-3,5-diyl)bis((4-hydroxyphenyl)methanone) With potassium carbonate In toluene at 25 - 30℃; for 0.5h;
Stage #2: cyclopentyl chloride In toluene at 25 - 30℃; for 5h;
87.8%
7-hydroxy-2,2-dimethyl-chroman-4-one
17771-33-4

7-hydroxy-2,2-dimethyl-chroman-4-one

cyclopentyl chloride
930-28-9

cyclopentyl chloride

7-(cyclopentyloxy)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one
120046-18-6

7-(cyclopentyloxy)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 22h;85%
(E)-1-([1,1'-biphenyl]-4-yl)-N-(4-methoxyphenyl)ethan-1-imine

(E)-1-([1,1'-biphenyl]-4-yl)-N-(4-methoxyphenyl)ethan-1-imine

cyclopentyl chloride
930-28-9

cyclopentyl chloride

1-(3-cyclopentyl-[1,1'-biphenyl]-4-yl)ethanone
1443686-20-1

1-(3-cyclopentyl-[1,1'-biphenyl]-4-yl)ethanone

Conditions
ConditionsYield
Stage #1: (E)-1-([1,1'-biphenyl]-4-yl)-N-(4-methoxyphenyl)ethan-1-imine; cyclopentyl chloride With neopentylmagnesium bromide; cobalt(II) bromide; 1,3-Diisopropyl-4,5-dihydro-3H-imidazol-1-ium tetrafluoroborate In tetrahydrofuran at 0 - 20℃; for 29h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran Inert atmosphere; Schlenk technique;
85%
With 1,3-diisopropylimidazolium tetrafluoroborate; neopentylmagnesium bromide; cobalt(II) bromide In tetrahydrofuran at 20℃; for 24h; Schlenk technique;85%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

p-cyclopentyltoluene
827-55-4

p-cyclopentyltoluene

Conditions
ConditionsYield
Stage #1: cyclopentyl chloride With [1,3-bis(3,5-di-tert-butyl-2-hydroxybenzyl)benzimidazolium][FeCl4] In diethyl ether at 0℃; for 0.0333333h; Schlenk technique; Inert atmosphere;
Stage #2: para-methylphenylmagnesium bromide In diethyl ether at 0 - 30℃; for 2h; Temperature; Schlenk technique; Inert atmosphere;
84%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

(Bicyclo<2.2.1>hept-5-en-2-yl)trimethoxysilan

(Bicyclo<2.2.1>hept-5-en-2-yl)trimethoxysilan

C14H24O2Si

C14H24O2Si

Conditions
ConditionsYield
Stage #1: cyclopentyl chloride With iodine; magnesium In tert-butyl methyl ether Inert atmosphere; Reflux;
Stage #2: (Bicyclo<2.2.1>hept-5-en-2-yl)trimethoxysilan In tert-butyl methyl ether Inert atmosphere; Reflux;
84%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

sodium cyanide
143-33-9

sodium cyanide

cyclopentanecarbonitrile
4254-02-8

cyclopentanecarbonitrile

Conditions
ConditionsYield
With tetrakis[tris(dimethylamino)phosphoranylideneamino]phosphonium chloride; tris phosphate In octane at 110℃; for 6h;82%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

fluorocyclopentane
1481-36-3

fluorocyclopentane

Conditions
ConditionsYield
With potassium fluoride; tetrakis[tris(dimethylamino)phosphoranylideneamino]phosphonium chloride; tris phosphate In DMF (N,N-dimethyl-formamide) at 110℃; for 6h;80%
With potassium fluoride; tetrakis[tris(dimethylamino)phosphoranylideneamino]phosphonium chloride In DMF (N,N-dimethyl-formamide) at 110℃; for 6h;68%
7,8-benzoquinoline
230-27-3

7,8-benzoquinoline

cyclopentyl chloride
930-28-9

cyclopentyl chloride

10-cyclopentylbenzo[h]quinoline

10-cyclopentylbenzo[h]quinoline

Conditions
ConditionsYield
With 1,3-diisopropylimidazolium tetrafluoroborate; neopentylmagnesium bromide; cobalt(II) bromide In tetrahydrofuran at 20℃; for 24h; Schlenk technique;80%
With iron(II) triflate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; lithium hexamethyldisilazane at 140℃; for 12h; regioselective reaction;76%
2-ethynylpyridine
1945-84-2

2-ethynylpyridine

cyclopentyl chloride
930-28-9

cyclopentyl chloride

2-(cyclopentylethynyl)pyridine
865173-44-0

2-(cyclopentylethynyl)pyridine

Conditions
ConditionsYield
With copper(l) iodide; C21H23ClNiP2S; caesium carbonate; sodium iodide In dimethyl sulfoxide at 50℃; for 12h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;80%
4-n-chlorophenylacetylene
873-73-4

4-n-chlorophenylacetylene

cyclopentyl chloride
930-28-9

cyclopentyl chloride

1-chloro-4-(cyclopentylethynyl)benzene

1-chloro-4-(cyclopentylethynyl)benzene

Conditions
ConditionsYield
With copper(l) iodide; C21H23ClNiP2S; caesium carbonate; sodium iodide In dimethyl sulfoxide at 50℃; for 12h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;79%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

dimethyl(phenyl)silyllithium
3839-31-4

dimethyl(phenyl)silyllithium

cyclopentyldimethyl(phenyl)silane

cyclopentyldimethyl(phenyl)silane

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere;74%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

1-(cyclopentylethynyl)-4-methoxybenzene

1-(cyclopentylethynyl)-4-methoxybenzene

Conditions
ConditionsYield
With copper(l) iodide; C21H23ClNiP2S; caesium carbonate; sodium iodide In dimethyl sulfoxide at 50℃; for 12h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;74%
cyclopentyl chloride
930-28-9

cyclopentyl chloride

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

cyclopentyl(diphenyl)phosphane
7650-81-9

cyclopentyl(diphenyl)phosphane

Conditions
ConditionsYield
With magnesium In diethyl ether at 20℃; Inert atmosphere;72%

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