2-Cyclopentenone supplier | CasNO.930-30-3

Name
2-Cyclopentenone
EINECS 213-213-0
CAS No. 930-30-3
Article Data151
CAS DataBase
Density 1.046 g/cm³
Solubility Almost insoluble in water, soluble in alcohol and ether
Melting Point
Formula C₅H₆O
Boiling Point 135.999 °C at 760 mmHg
Molecular Weight 82.102
Flash Point 40.045 °C
Transport Information UN 1224 3/PG 3
Appearance Clear yellow liquid
Safety 16-36-36/37/39
Risk Codes 10-37-36/37/38-22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms 1-Cyclopenten-3-one;1-Cyclopenten-5-one;2-Cyclopentenone;Cyclopenten-3-one;NSC 73117;2-Cyclopenten-1-one;
PSA 17.07000
LogP 0.90550

Synthetic route

: 130249-17-1, 6705-52-8
2,3-epoxycyclopentanone

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With Amberlyst 15; sodium iodide In acetone at 20℃; for 3h; deoxygenation;	96%

: 33698-60-1
hepta-1,6-dien-3-one

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With [1,3-bis-mesityl-imidazolidin-2-yl]Cl2(PCp3)Ru=CHCH=CMe2 In dichloromethane for 12h; metathesis; Heating;	93%

: 35466-83-2
allyl methyl carbonate

: 933-06-2
1-acetoxycyclopentene

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
palladium diacetate In acetonitrile	93%

: 10493-98-8
2-hydroxy-2-cyclopenten-1-one

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
	93%

: 1056246-36-6
2-bromocyclopentanone

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With lithium carbonate; hydroquinone; lithium bromide In DMF (N,N-dimethyl-formamide) at 100℃; for 4h;	91.8%

: 19980-43-9
1-(trimethylsilyloxy)cyclopentene

A: 930-30-3
cyclopent-2-enone

B: 120-92-3
cyclopentanone

Conditions

Conditions	Yield
With oxygen; palladium matal-containing silica-supported catalyst In various solvent(s) at 59.9℃; for 24h; Product distribution; Mechanism; Pd(0) supported on various zeolites , influence of calcination and reaction temperature and of the solvent;	A 90.1% B n/a
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h; Product distribution; solvent;	A 90.1% B 0.8%
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h; Yields of byproduct given;	A 90.1% B n/a
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h;	A 90.1% B 0.8%

: 695-56-7
1,4-dioxaspiro[4.4]non-6-ene

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With cerium(III) chloride; sodium iodide In acetonitrile for 0.5h; Ambient temperature;	90%
With silica gel; iron(III) chloride at 20℃; for 0.166667h;	87%
With ammonium cerium(IV) nitrate In methanol; water at 20℃; for 0.166667h; Ring cleavage;	86%

: 3212-60-0, 6426-28-4, 62894-08-0, 109431-72-3
cyclopent-2-enol

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(ll) bromide In water; acetonitrile at 20℃; for 3.7h; Inert atmosphere;	90%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; iron(III) chloride In water; ethyl acetate at 20℃; for 2h;	78%
With 4-Phenylpyridine 1-oxide; chloro{bis-N,N'-(salicylaldehyde)ethylenediiminato}chromium(III); iodosylbenzene In dichloromethane at 20℃; for 14h; Oxidation;	74 % Turnov.

: 80522-45-8
1-triisopropylsilyl(oxy)-cyclopentene

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; disodium hydrogenphosphate; oxygen; palladium dihydroxide In dichloromethane at 24℃; for 42h;	88%

: 142-29-0
cyclopentene

A: 930-30-3
cyclopent-2-enone

B: 120-92-3
cyclopentanone

Conditions

Conditions	Yield
With methanesulfonic acid; oxygen; palladium diacetate; molybdovanadophosphate/C In water; acetonitrile at 50℃; for 6h; Wacker-type oxidation;	A 1% B 85%
With methanesulfonic acid; oxygen; palladium diacetate; molybdovanadophosphate/C In ethanol; water at 50℃; for 6h; Wacker-type oxidation;	A 6% B 75%

: 41820-27-3
Δ3-dimethyl dihydromuconate

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With water; Al2O3#dotK2O at 400℃; Industry scale;	85%

: 279-35-6
1,3-epiperoxycyclopentane

A: 930-30-3
cyclopent-2-enone

B: 626-96-0
4-oxopentanal

C: 26831-63-0
rac-3-hydroxycyclopentanone

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane Rate constant; Product distribution; Et3N, Dabco, Dabco+AcOH in C6D6; Me4NOAc in CD3Cl;	A n/a B 82% C n/a
With 1,4-diaza-bicyclo[2.2.2]octane; acetic acid In benzene-d6 0 deg C -> 45 deg C, 65 h;

...Expand

: 94726-41-7
3-(tri-n-butyl)stannylcyclopentan-1-one

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile at 60℃; for 1h; cleavage;	81%

: 78522-00-6, 78549-40-3
(1R,2R,3R)-2,3-Dibromo-cyclopentanol

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With potassium hydroxide In diethyl ether at 0℃; for 1h;	80%

: 120-92-3
cyclopentanone

A: 930-30-3
cyclopent-2-enone

B: 7027-34-1
[1,1'-bi(cyclopentan)]-1'-en-2-one

Conditions

Conditions	Yield
ruthenium trichloride for 48h; Condensation; Heating;	A 8% B 80%

: 142-29-0
cyclopentene

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) iodide In water; acetonitrile at 45℃; for 0.5h; Reagent/catalyst; Temperature;	79%
With pyridine; dmap; 5,10,15,20-tetrakisphenylporphyrin; oxygen; acetic anhydride In dichloromethane for 2h; Irradiation;	71%
With tert.-butylhydroperoxide; potassium carbonate; 2.5 mol percent Pd on charcoal In dichloromethane at 0℃;	71%

: 57702-56-4
cis- and trans-4-cumyloxy-2-cyclopentenol

A: 930-30-3
cyclopent-2-enone

B: 98-83-9
isopropenylbenzene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 105℃;	A 76.6% B n/a

: 120-92-3
cyclopentanone

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With iodic acid; dimethyl sulfoxide at 45℃; for 6h;	74%
With allyl diethyl phosphate; sodium carbonate; palladium diacetate In tetrahydrofuran at 86℃; for 21h;	63%
With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 7h; Sealed tube;	51%

: 14579-07-8
1-(trimethylsilyl)cyclopentene

A: 930-30-3
cyclopent-2-enone

B: 156518-14-8
2-(trimethylsilyl)-2-cyclopentenyl hydroperoxide

Conditions

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane at -10 - -5℃; for 2.5h; Irradiation; Yields of byproduct given;	A n/a B 72%

: 19931-06-7
5-Chlor-2-cyclopenten-1-on

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With water; zinc In dimethyl sulfoxide; benzene at 25℃; for 6h;	71%

: 86950-87-0
allyl cyclopent-1-en-1-yl carbonate

A: 930-30-3
cyclopent-2-enone

B: 30079-93-7
2-allylcyclopentanone

C: 120-92-3
cyclopentanone

Conditions

Conditions	Yield
palladium diacetate; triphenylphosphine In acetonitrile for 1.5h; Heating; Yields of byproduct given;	A 71% B n/a C n/a

...Expand

: 29268-42-6
bicyclo<3.2.0>heptan-2-one

A: 930-30-3
cyclopent-2-enone

B: 74-85-1
ethene

Conditions

Conditions	Yield
at 580 - 600℃;	A 70% B n/a

: 19980-43-9
1-(trimethylsilyloxy)cyclopentene

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With diallylcarbonate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane In benzonitrile for 1h; Heating;	69%
With allyl methyl carbonate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane In acetonitrile Heating;	81 % Chromat.
Multi-step reaction with 2 steps 1: 77 percent / CH2Cl2 / 25 °C 2: 1) O3 2) Et2NH / 1) CH2Cl2 / -78 deg C 2) CCl4 / reflux View Scheme
With 2,4,6-trimethyl-pyridine; sodium hexafluoroantimonate; Graphite In acetonitrile at 20℃; Electrochemical reaction; Inert atmosphere;	33 %Chromat.

: 98-01-1
furfural

A: 930-30-3
cyclopent-2-enone

B: 120-92-3
cyclopentanone

Conditions

Conditions	Yield
With hydrogen In water at 160℃; under 30003 Torr; for 1.2h; Autoclave;	A 31% B 69%
With water; hydrogen at 160℃;
Multi-step reaction with 2 steps 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / Autoclave 2: hydrogen; water / 160 °C / Autoclave View Scheme

: 98-00-0
(2-furyl)methyl alcohol

A: 930-30-3
cyclopent-2-enone

B: 120-92-3
cyclopentanone

Conditions

Conditions	Yield
With water; zinc at 250℃; for 2.33333h; Autoclave;	A 66.1% B 9.4%
With water; hydrogen at 160℃; Autoclave;

: 104755-25-1
C11H12Cl2OSe

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water	64%
With sodium hydrogencarbonate In dichloromethane for 4h;	64%

: 98-00-0
(2-furyl)methyl alcohol

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With hydrogen In water at 150℃; under 15001.5 Torr; Pressure; Reagent/catalyst; Autoclave; Green chemistry;	61.5%
With hydrogen In hexane; water at 150℃; for 6h; Reagent/catalyst; Solvent; Temperature; Autoclave;	52.3%
Multi-step reaction with 2 steps 1: hydrogen; water / 8 h / 160 °C / Inert atmosphere; Autoclave 2: hydrogen; water / 160 °C / Autoclave View Scheme

: 57260-93-2
4-methylsulfinyl-4-methylthio-1-cyclopentene

A: 930-30-3
cyclopent-2-enone

B: 14320-37-7
3-Cyclopentenon

Conditions

Conditions	Yield
With sulfuric acid In water; acetone for 5h; Ambient temperature;	A 6% B 60%

: 98-01-1
furfural

: 930-30-3
cyclopent-2-enone

Conditions

Conditions	Yield
With [(pentamethylcyclopentadienyl)IrIII(4,4’-dihydroxy-2,2’-bipyridine)(H2O)]SO4; alumina; hydrogen In water at 130℃; under 22502.3 Torr; for 4h; Autoclave;	60%
With water; zinc at 250℃; for 2.33333h; Autoclave;	23.1%
Multi-step reaction with 2 steps 1: water / 4 h / 160 °C / 750.08 Torr / Inert atmosphere; Autoclave 2: hydrogen; water / 160 °C / Autoclave View Scheme

: 930-30-3
cyclopent-2-enone

: 19093-37-9
allyl phenyl sulfoxide

: 77548-22-2
1-(3-oxocyclopentyl)-3-phenylsulfinyl-2-(E)-propene

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane Product distribution; 1.) -78 deg C, 90 min; 2.) -78 deg C, 1.0 h; other temperature, other time;	100%
With hydrogenchloride; lithium diisopropyl amide 1.) THF, hexane, -78 to 20 deg C, 1.5 h, then 20 deg C, 30 min; 2.) -78 deg C, 1 h; Yield given. Multistep reaction;

: 930-30-3
cyclopent-2-enone

: 34948-25-9
n-butylcopper

: 84131-68-0
rac-3-butylcyclopentanone

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; chloro-trimethyl-silane; lithium iodide In various solvent(s) at -78℃; for 0.1h;	100%

: 930-30-3
cyclopent-2-enone

: 75839-80-4
S-tert-butyl cyanothiolacetate

: 104725-25-9, 104725-49-7
Cyano-(3-oxo-cyclopentyl)-thioacetic acid S-tert-butyl ester

Conditions

Conditions	Yield
With chloro-trimethyl-silane; sodium hydride In benzene at 10℃; for 3h;	100%

: 930-30-3
cyclopent-2-enone

: 120-92-3
cyclopentanone

Conditions

Conditions	Yield
With limonene.; palladium on activated charcoal for 0.5h; Heating;	100%
With hydrogen; SC-1 Ni2B In methanol at 25℃; under 760 Torr; for 24h;	100%
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 0.5h; Ambient temperature;	99%

: 930-30-3
cyclopent-2-enone

: 141-97-9
ethyl acetoacetate

: 66077-94-9
ethyl 3-oxo-2-(3-oxocyclopentyl)butanoate

Conditions

Conditions	Yield
With hydrotalcite at 80℃; for 6h; Michael addition;	100%
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 25℃; for 10h; Michael reaction;	99%
With zinc trifluoromethanesulfonate at 20℃; for 6h;	95%

: 930-30-3
cyclopent-2-enone

: 108-98-5
thiophenol

: 75717-34-9
3-(phenylthio)cyclopentan-1-one

Conditions

Conditions	Yield
triethylamine In chloroform for 2h; Ambient temperature;	100%
With SBA-15 supported (N-heterocyclic carbene)copper(I) complex In 1,2-dichloro-ethane at 100℃; for 48h; Schlenk technique; Glovebox; Inert atmosphere; stereoselective reaction;	99%
With tetra(n-butyl)ammonium hydroxide In ethanol; water at 20℃; for 0.0333333h; Catalytic behavior; Solvent; Michael Addition; Green chemistry;	99%

: 930-30-3
cyclopent-2-enone

: 13716-45-5
diethyl trimethylsilyl phosphite

: 81435-28-1
(3-Trimethylsilanyloxy-cyclopent-2-enyl)-phosphonic acid diethyl ester

Conditions

Conditions	Yield
In acetonitrile at 180℃; for 12h;	100%

: 930-30-3
cyclopent-2-enone

: 105-53-3
diethyl malonate

: 91766-21-1
3-(bis(ethoxycarbonyl)methyl)cyclopentanone

Conditions

Conditions	Yield
With hydrotalcite at 80℃; for 6h; Michael addition;	100%
With montmorillonite-enwrapped copper at 100℃; for 14h; Michael reaction;	91%
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 25℃; for 0.5h; Michael reaction;	90%

: 104-53-0
3-phenyl-propionaldehyde

: 930-30-3
cyclopent-2-enone

: 273219-46-8
2-(1-hydroxy-3-phenylpropyl)-2-cyclopenten-1-one

Conditions

Conditions	Yield
With tributylphosphine; 1,1'-bi-2-naphthol In tetrahydrofuran at 20℃; for 1h; Baylis-Hillman addition;	100%
With Dimethyl(phenyl)phosphine In methanol; chloroform at 20℃; for 23h; Morita-Baylis-Hillman reaction;	98%
With sodium phenoxide; tris[tert-butyl]phosphonium tetrafluoroborate In tetrahydrofuran at 20℃; for 1h; Baylis-Hillman reaction;	95%

: 930-30-3
cyclopent-2-enone

: 124-13-0
Octanal

: 2-(1-hydroxy-octyl)-cyclopent-2-enone

Conditions

Conditions	Yield
With tributylphosphine; 1,1'-bi-2-naphthol In tetrahydrofuran at 20℃; for 3h; Baylis-Hillman addition;	100%

: 930-30-3
cyclopent-2-enone

: 130914-24-8
chlorodicyclopentylphosphine

: 3-(dicyclopentylphosphinoyl)cyclopentanone

Conditions

Conditions	Yield
With 4 A molecular sieve; acetic acid at 20℃; for 2h;	100%

: 930-30-3
cyclopent-2-enone

: 98-80-6
phenylboronic acid

: 64145-51-3
3-phenylcyclopentanone

Conditions

Conditions	Yield
With chloroform; caesium carbonate; triphenylphosphine; palladium diacetate In toluene at 80℃; for 24h;	100%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium carbonate In water at 80℃; for 1h;	99%
With tert-butyl-amphos chloride; sodium dodecyl-sulfate; sodium carbonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene at 20℃;	99%

: 930-30-3
cyclopent-2-enone

: 55107-14-7
Methyl 4,4-dimethyl-3-oxopentanoate

: (+)-4,4-dimethyl-3-oxo-2-(3-oxocyclopentyl)pentanoic acid methyl ester

Conditions

Conditions	Yield
Ru[(S,S)-Msdpen](η6-hexamethylbenzene) In toluene at 30℃; for 24h; Michael reaction;	100%

: 930-30-3
cyclopent-2-enone

: 5720-07-0
4-methoxyphenylboronic acid

: 155325-51-2
(R)-3-(4-methoxyphenyl)cyclopentan-1-one

Conditions

Conditions	Yield
With potassium hydroxide; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene; bis(ethylene)rhodium(I) chloride dimer In 1,4-dioxane; water at 50℃; for 1h;	100%
With chlorobis(ethylene)rhodium(I) dimer; C22H20N2O4; potassium hydroxide In ethanol at 30℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	98%
With chlorobis(ethylene)rhodium(I) dimer; (R)-6,6'-dimethoxy-P2,P2,P2',P2'-tetrakis-[4-(trifluoromethyl)phenyl]-biphenyl-2,2'-bisphosphine; potassium hydroxide In water; toluene at 20℃; for 6.5h; Inert atmosphere; optical yield given as %ee; stereoselective reaction;	96%

: 930-30-3
cyclopent-2-enone

: 98-80-6
phenylboronic acid

: 64145-51-3, 86505-50-2, 141662-68-2, 86505-44-4
(R)-3-phenylcyclopentanone

Conditions

Conditions	Yield
With chlorobis(ethylene)rhodium(I) dimer; (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene; potassium hydroxide In methanol; dichloromethane at 20℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	100%
With potassium hydroxide; (R,R)-tetrafluorobenzobarrelene rhodium catalyst In 1,4-dioxane at 30℃; for 1h;	99%
With chlorobis(ethylene)rhodium(I) dimer; C22H20N2O4; potassium hydroxide In ethanol at 30℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

: 930-30-3
cyclopent-2-enone

: 95124-07-5
dimethyl (prop-2-yn-1-yl)malonate

: 868388-53-8
2-(3-oxocyclopentyl)-2-prop-2-ynylmalonic acid dimethyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 10h;	70%

: 930-30-3
cyclopent-2-enone

: 93102-05-7
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

: 185692-51-7
7-Benzyl-2-oxo-7-azabicyclo[3.3.0]octane

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h;	100%
With trifluoroacetic acid In dichloromethane at 20 - 25℃; for 5h;	81.4%
With trifluoroacetic acid In dichloromethane at -5 - 0℃;

: 930-30-3
cyclopent-2-enone

: 93102-05-7
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

: 174293-33-5
(3aS,6aR)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 18h;	100%
With trifluoroacetic acid In dichloromethane at 20℃; for 18h;	100%
With trifluoroacetic acid In dichloromethane at 0 - 20℃; Inert atmosphere;	84%

: 930-30-3
cyclopent-2-enone

: 1219624-35-7
1-methoxy-N-(3-(trifluoromethyl)benzyl)-N-((trimethylsilyl)methyl)methanamine

: 2-(3-(trifluoromethyl)benzyl)hexahydrocyclopenta[c]pyrrol-4(5H)-one

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.75h; Inert atmosphere;	100%

: 930-30-3
cyclopent-2-enone

: 151169-75-4
3,4-dichlophenylboronic acid

: 1429345-63-0
(S)-3-(3,4-dichlorophenyl)cyclopentanone

Conditions

Conditions	Yield
Stage #1: 3,4-dichlophenylboronic acid With bis(norbornadiene)rhodium(l)tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Stage #2: cyclopent-2-enone With triethylamine In 1,4-dioxane; water at 20℃; for 18h;	100%
Stage #1: 3,4-dichlophenylboronic acid With bis(norbornadiene)rhodium(l)tetrafluoroborate; (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Stage #2: cyclopent-2-enone With triethylamine In 1,4-dioxane; water at 20℃; for 18h;	100%

: 930-30-3
cyclopent-2-enone

: 5-cyclopropyl-1-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-1H-pyrazole-4-carboxylic acid methyl ester

: 5-cyclopropyl-1-[3-(3-oxocyclopentyl)phenyl]-1H-pyrazole-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine In 1,4-dioxane; water at 20 - 100℃; for 18h; Concentration; Temperature;	100%

: 693-03-8
n-butyl magnesium bromide

: 75-77-4
chloro-trimethyl-silane

: 930-30-3
cyclopent-2-enone

: 108643-82-9
((3-butylcyclopent-1-en-1-yl)oxy)trimethylsilane

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide In tetrahydrofuran at -78℃;	99%

...Expand

: 930-30-3
cyclopent-2-enone

: 51263-39-9
(Z)-ethyl 2-bromobut-2-enoate

: 105230-72-6, 105307-94-6, 122090-17-9, 122090-18-0
2-Oxo-6-vinyl-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.25h;	99%

: 930-30-3
cyclopent-2-enone

: 3839-31-4
dimethyl(phenyl)silyllithium

: 109023-10-1
3-(dimethyl(phenyl)silyl)cyclopentanone

Conditions

Conditions	Yield
With copper(I) iodide dimethyl sulfide complex In tetrahydrofuran at -78 - 0℃; for 11h;	99%
With copper(l) cyanide 1.) THF, 0 deg C, 20 min, 2.) THF, -78 deg C, 2 h; Yield given. Multistep reaction;

: 930-30-3
cyclopent-2-enone

: 10481-34-2
2-bromo-2-cyclopenten-1-one

Conditions

Conditions	Yield
With pyridine N-oxide; N-Bromosuccinimide In acetonitrile at 0 - 20℃; Inert atmosphere;	99%
With bromine; triethylamine In dichloromethane	98%
Stage #1: cyclopent-2-enone With hydrogen bromide In dichloromethane at -20℃; for 0.0833333h; Inert atmosphere; Stage #2: With bromine In dichloromethane at -24 - -20℃; for 1.5h; Inert atmosphere; Stage #3: With pyridine In dichloromethane at -20 - 0℃; Inert atmosphere;	97%

: 930-30-3
cyclopent-2-enone

: 33948-35-5
2-iodo-cyclopent-2-enone

Conditions

Conditions	Yield
With dmap; iodine; potassium carbonate In tetrahydrofuran for 1h;	99%
With dmap; iodine; potassium carbonate In tetrahydrofuran; water at 25 - 30℃; for 4h;	99%
With pyridine; iodine In dichloromethane Ambient temperature; further amines as reagents;	96%

: 930-30-3
cyclopent-2-enone

: 555-16-8
4-nitrobenzaldehdye

: 2-[hydroxy(4-nitrophenyl)methyl]-2-cyclopenten-1-one

Conditions

Conditions	Yield
With pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane; sodium hydrogencarbonate In tetrahydrofuran; water at 25℃; for 40h; Baylis-Hillman Reaction;	99%
With dmap; N,N,N,N,-tetramethylethylenediamine; magnesium iodide In methanol at 20℃; for 5h; Morita-Baylis-Hillman reaction; Inert atmosphere;	94%
With 1H-imidazole In tetrahydrofuran; water at 20℃; for 16h; Product distribution; Further Variations:; Solvents;	92%

: 930-30-3
cyclopent-2-enone

: 557-20-0
diethylzinc

: 86505-42-2, 86505-49-9, 10264-55-8
3-ethylcyclopentanone

Conditions

Conditions	Yield
With 1-[3-((S)-1-hydroxy-3,3-dimethyl-2-butanylamino)-3-oxopropyl]-3-benzylbenzimidazolium iodide; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran; hexane at 20℃; for 3h;	99%
Stage #1: diethylzinc With [3-[(1R,2R)-2-(3,5-di-tert-butyl-2-hydroxybenzylamino)cyclohexyl]-1-isopropyl-4-phenyl-3H-imidazol-1-ylidene]copper(I) bromide In diethyl ether at 25℃; for 0.25h; Inert atmosphere; Stage #2: cyclopent-2-enone In diethyl ether at 25℃; for 1.16667h; Inert atmosphere; Stage #3: With hydrogenchloride; water In diethyl ether	91%
With copper(I) trifluoromethanesulfonate benzene complex; (+)-3-((tert-butyldimethylsilyl)oxy)-8-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxa-phosphepin-4-yl)-8-azabicyclo[3.2.1]oct-6-ene In hexane; dichloromethane at 0℃; for 12h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere; Schlenk technique;	68%

: 930-30-3
cyclopent-2-enone

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: ethyl 2-oxo-(3-oxocyclopentyl)cyclopentanecarboxylate

Conditions

Conditions	Yield
europium-containing poly(2,4-OH2-C6H4COO--co-HCHO)-gel In tetrachloromethane for 10h; Michael addition; Heating;	99%
silica gel; ytterbium(III) triflate for 144h; Ambient temperature;	87%
With trifluoroacetic acid In acetonitrile at 20℃; for 60h; Addition; Michael addition;	72%

: 930-30-3
cyclopent-2-enone

: 98-80-6
phenylboronic acid

: 64145-51-3, 86505-44-4, 141662-68-2, 86505-50-2
(S)-3-phenylcyclopentanone

Conditions

Conditions	Yield
With potassium phosphate; chlorobis(ethylene)rhodium(I) dimer; C25H27NO3S In 1,4-dioxane; water at 60℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%
Stage #1: phenylboronic acid With chlorobis(ethylene)rhodium(I) dimer; (R)-N-cinnamyl-2-methylpropane-2-sulfinamide In 1,4-dioxane at 40℃; for 0.5h; Inert atmosphere; Stage #2: cyclopent-2-enone With potassium phosphate In 1,4-dioxane; water at 40℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%
With chlorobis(ethylene)rhodium(I) dimer; (R)-(+)-[(η5-1-bis(3,5-dimethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 50℃; for 7h; Inert atmosphere; enantioselective reaction;	99%

2-Cyclopentenone Specification

The 2-2-Cyclopentenone with CAS registry number of 930-30-3 is also known as 2-Cyclopentenone. The IUPAC name is Cyclopent-2-en-1-one. It belongs to product categories of Ring Systems; C3 to C6; Carbonyl Compounds; Ketones. Its EINECS registry number is 213-213-0. In addition, the formula is C₅H₆O and the molecular weight is 82.10. This chemical is a clear yellow liquid that almost insoluble in water but soluble in alcohol and ether. What's more, it may cause inflammation to the skin or other mucous membranes and may cause damage to health. It should be sealed at the temperature of 4 °C at room temperature away from oxidants.

Physical properties about 2-2-Cyclopentenone are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 20.652; (4)ACD/KOC (pH 7.4): 20.652; (5)#H bond acceptors: 1; (6)Index of Refraction: 1.492; (7)Molar Refractivity: 22.793 cm³; (8)Molar Volume: 78.507 cm³; (9)Surface Tension: 36.818 dyne/cm; (10)Density: 1.046 g/cm³; (11)Flash Point: 40.045 °C; (12)Enthalpy of Vaporization: 37.34 kJ/mol; (13)Boiling Point: 135.999 °C at 760 mmHg; (14)Vapour Pressure: 7.529 mmHg at 25 °C.

Preparation of 2-2-Cyclopentenone: it is prepared by elimination of α-bromo-cyclopentanone using lithium carbonate and claisen condensation-decarboxylation-isomerization cascades of unsaturated diesters.

2-2-Cyclopentenone is prepared by elimination of α-bromo-cyclopentanone

Uses of 2-2-Cyclopentenone: it is used to produce 1-deuterio-2-cyclopentenol. The reaction occurs with reagent LiAlD₄ and solvent diethyl ether with other condition of heating for 15 minutes. The yield is about 84%.

2-2-Cyclopentenone is used to produce 1-deuterio-2-cyclopentenol.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It also is flammable and harmful if swallowed. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1CC(=O)C=C1
2. InChI: InChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2
3. InChIKey: BZKFMUIJRXWWQK-UHFFFAOYSA-N

Product Name

2-Cyclopentenone

Synthetic route

2-Cyclopentenone Specification

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