Product Name

  • Name

    Cyclopentene oxide

  • EINECS 206-005-6
  • CAS No. 285-67-6
  • Article Data74
  • CAS DataBase
  • Density 1.071 g/cm3
  • Solubility Immiscible with water.
  • Melting Point 136-137 °C
  • Formula C5H8O
  • Boiling Point 102 °C at 760 mmHg
  • Molecular Weight 84.1179
  • Flash Point 10 °C
  • Transport Information UN 1993 3/PG 2
  • Appearance Clear colorless to very faintly yellow liquid
  • Safety 16-26-36-36/37/39
  • Risk Codes 11-36/37/38
  • Molecular Structure Molecular Structure of 285-67-6 (Cyclopentene oxide)
  • Hazard Symbols FlammableF,IrritantXi
  • Synonyms 1,2-Epoxycyclopentane;Cyclopentane, 1,2-epoxy-;Cyclopentene epoxide;Epoxycyclopentane;NSC 148216;NSC 196230;cis-1,2-Epoxycyclopentane;
  • PSA 12.53000
  • LogP 0.93770

Synthetic route

cyclopentene
142-29-0

cyclopentene

Cyclopentene oxide
285-67-6

Cyclopentene oxide

Conditions
ConditionsYield
With [NiII(tetrakis(2,6-di(n-butoxy)phenyl)porphyrinato)]; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;100%
With dihydrogen peroxide; teterabutylammonium In acetonitrile at 31.85℃; for 3h;99%
With tert.-butylhydroperoxide In acetonitrile at 65 - 68℃; for 9h;99%
cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

cyclopentane-1,2-diol
4065-92-3

cyclopentane-1,2-diol

Conditions
ConditionsYield
With sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In 5,5-dimethyl-1,3-cyclohexadiene; water at 60℃; for 2h; pH=1.6; Kinetics; Reagent/catalyst; Solvent;A 5.9%
B 93.4%
(C4H9)3SnOC5H8Cl

(C4H9)3SnOC5H8Cl

Cyclopentene oxide
285-67-6

Cyclopentene oxide

Conditions
ConditionsYield
decompn. at 200°C for 0.5 h;86%
4-cyano-N,N-dimethylaniline-N-oxide
62820-00-2

4-cyano-N,N-dimethylaniline-N-oxide

cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

4-cyano-N-methylaniline
4714-62-9

4-cyano-N-methylaniline

C

4-cyano-N,N-dimethylaniline
1197-19-9

4-cyano-N,N-dimethylaniline

Conditions
ConditionsYield
With 1H-imidazole; [Mn(2,3,7,8,12,13,17,18-octamethyl-5,10,15,20-tetraphenylporphyrin)Cl] In dichloromethane at 25℃; Product distribution; with various alkene concentrations;A 80%
B 20%
C 79%
(C4H9)3SnOC5H8Br

(C4H9)3SnOC5H8Br

Cyclopentene oxide
285-67-6

Cyclopentene oxide

Conditions
ConditionsYield
decompn. at 100°C for 0.5 h;73%
decompn. at 100°C for 0.5 h;73%
trans-cyclopentane-1,2-diol
5057-99-8

trans-cyclopentane-1,2-diol

Cyclopentene oxide
285-67-6

Cyclopentene oxide

Conditions
ConditionsYield
With sodium hydroxide; p-toluenesulfonyl chloride; benzyltriethylammonium bromide In dichloromethane at 25℃; for 0.166667h;71%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

tert. Butyl-2-cyclopenten-1-yl-peroxid
38362-74-2

tert. Butyl-2-cyclopenten-1-yl-peroxid

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 0℃; for 48h;A n/a
B 63%
cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

cyclopentane-1,2-diol
4065-92-3

cyclopentane-1,2-diol

C

Glutaraldehyde
111-30-8

Glutaraldehyde

Conditions
ConditionsYield
With dihydrogen peroxide; H3PMo10W2O40 at 35℃; for 3h;A 0.8%
B 13.9%
C 60.6%
With dihydrogen peroxide; H3PMo10W2O40 at 35℃; for 3h; Product distribution; various molybdenum compounds as catalysts;A 0.8%
B 13.9%
C 60.6%
cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

C

cyclopent-2-enone
930-30-3

cyclopent-2-enone

Conditions
ConditionsYield
With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-); urea hydrogen peroxide adduct In acetonitrile at 70℃; for 24h; Ene Reaction;A 10%
B 32%
C 58%
With oxygen In chlorobenzene at 50℃; Mechanism; Product distribution; catalysts Co(acac)3 and MoO2(acac)2;A 10.4 % Chromat.
B n/a
C n/a
With air; iron 5,10,15,20-tetrakis-(2',6'-dichlorophenyl)porphyrinate; iodosylbenzene In dichloromethane for 0.5h; Product distribution; Mechanism; var. cycloalkenes; other porphyrin; var. reaction time;A 64 % Chromat.
B 19 % Chromat.
C 1.9 % Chromat.
cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 65 - 68℃; for 9h;A 39%
B 16%
With sodium hypochlorite In acetonitrile at 65 - 68℃; for 9h;A 5%
B 14%
With oxygen; isobutyraldehyde at 50℃; for 6h; Catalytic behavior; Reagent/catalyst;A 89 %Chromat.
B 11 %Chromat.
2-chlorocyclopentane-1-ol
69578-06-9

2-chlorocyclopentane-1-ol

Cyclopentene oxide
285-67-6

Cyclopentene oxide

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide; diethyl ether
trifluoroacetyl peroxide
359-48-8

trifluoroacetyl peroxide

cyclopentene
142-29-0

cyclopentene

Cyclopentene oxide
285-67-6

Cyclopentene oxide

Conditions
ConditionsYield
With dichloromethane; sodium carbonate
2-t-butylperoxycyclopentane-1-yl
90466-76-5

2-t-butylperoxycyclopentane-1-yl

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

cyclopentyl t-butyl peroxide
56141-93-6

cyclopentyl t-butyl peroxide

Conditions
ConditionsYield
With tri-n-butyl-tin hydride In benzene at 24.9℃; Rate constant; Irradiation;
4-cyano-N,N-dimethylaniline-N-oxide
62820-00-2

4-cyano-N,N-dimethylaniline-N-oxide

cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

4’-cyano-N-methylformanilide
97860-68-9

4’-cyano-N-methylformanilide

C

4-cyano-N-methylaniline
4714-62-9

4-cyano-N-methylaniline

D

N,N'-dimethyl-N,N'-bis-(p-cyanophenyl)hydrazine
79121-26-9

N,N'-dimethyl-N,N'-bis-(p-cyanophenyl)hydrazine

E

N,N'-bis-(p-cyanophenyl)-N-methylmethylenediamine
97860-69-0

N,N'-bis-(p-cyanophenyl)-N-methylmethylenediamine

F

4-cyano-N,N-dimethylaniline
1197-19-9

4-cyano-N,N-dimethylaniline

Conditions
ConditionsYield
With (2,3,7,8,12,13,17,18-octamethyl-5,10,15,20-tetraphenylporphinato)iron(III) chloride In dichloromethane at 25℃; Product distribution;
3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole
76847-41-1

3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole

cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

3-bromo-4,5-dihydro-5-hydroxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole
76847-42-2

3-bromo-4,5-dihydro-5-hydroxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole

Conditions
ConditionsYield
In chloroform-d1 at 34℃; Rate constant;A 41 % Spectr.
B 41 % Spectr.
cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

cyclopent-2-enone
930-30-3

cyclopent-2-enone

Conditions
ConditionsYield
With oxygen 1.) 35 deg C, 101.3 kPa; 2.) pyrolysis GLC; Multistep reaction;
With Ce0.3Co0.7Fe2O4; dihydrogen peroxide In 1,4-dioxane at 90℃; for 9h;A 76.7 %Chromat.
B 11.6 %Chromat.
With Ca0.1Co0.9Fe2O4; dihydrogen peroxide In N,N-dimethyl-formamide at 60℃; for 8h; Catalytic behavior; Solvent; Reagent/catalyst; Schlenk technique;
cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

cyclopent-1-en-3-yl hydroperoxide
4096-28-0

cyclopent-1-en-3-yl hydroperoxide

C

2-(Cyclopent-2-enylperoxy)-cyclopentyl-hydroperoxide
4065-77-4

2-(Cyclopent-2-enylperoxy)-cyclopentyl-hydroperoxide

Conditions
ConditionsYield
With oxygen at 35℃; under 759.8 Torr;A 14 % Chromat.
B n/a
C n/a
With 2,2'-azobis(isobutyronitrile); oxygen at 35℃; under 759.8 Torr; for 145h; Mechanism; Product distribution; quantity mol O2 per mol olefine;A 14 % Chromat.
B n/a
C n/a
With oxygen at 35℃; under 759.8 Torr;
With oxygen at 35℃; under 759.8 Torr; Yield given. Yields of byproduct given;
cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

C

cyclopent-2-enone
930-30-3

cyclopent-2-enone

D

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With bis(acetonitrile)chloronitropalladium(II) In dichloromethane at 20℃; for 6h; Product distribution; other cycloalkenes;A 4 % Chromat.
B 27 % Chromat.
C 1 % Chromat.
D 3 % Chromat.
1-Bromo-2-tert-butylperoxy-cyclopentane

1-Bromo-2-tert-butylperoxy-cyclopentane

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

cyclopentyl t-butyl peroxide
56141-93-6

cyclopentyl t-butyl peroxide

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; trans-di-O-tert-butyl hyponitrite In benzene for 1.5h; Rate constant;
trans-2-bromomercurio-1-t-butylperoxycyclopentane

trans-2-bromomercurio-1-t-butylperoxycyclopentane

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

cyclopentyl t-butyl peroxide
56141-93-6

cyclopentyl t-butyl peroxide

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In dichloromethane 1.) 0 deg C, 30 min, 2.) room temperature, 30 min; Yield given. Yields of byproduct given;
cyclopentene
142-29-0

cyclopentene

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

but-2-enyl hydroperoxide
29314-30-5

but-2-enyl hydroperoxide

Conditions
ConditionsYield
With oxygen at 35℃; regioselectivity of the autooxidation; other cyclic olefins;
Cyclopentane
287-92-3

Cyclopentane

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

ethene
74-85-1

ethene

C

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

D

buta-1,3-diene
106-99-0

buta-1,3-diene

E

cyclopentene
142-29-0

cyclopentene

F

acrolein
107-02-8

acrolein

G

propene

propene

Conditions
ConditionsYield
With hydrogen; oxygen at 399.9℃; Product distribution; Rate constant; Mechanism; various O2 pressure; other reaction temperature;
(+/-)-trans-2-iodocyclopentanol
57857-90-6, 89417-14-1, 116051-23-1, 122673-93-2

(+/-)-trans-2-iodocyclopentanol

silver nitrate

silver nitrate

Cyclopentene oxide
285-67-6

Cyclopentene oxide

(+/-)-trans-2-chlorocyclopentanol
20377-80-4

(+/-)-trans-2-chlorocyclopentanol

aqueous NaOH

aqueous NaOH

Cyclopentene oxide
285-67-6

Cyclopentene oxide

water
7732-18-5

water

(+/-)-trans-2-amino-cyclopentanol; hydrogenoxalate

(+/-)-trans-2-amino-cyclopentanol; hydrogenoxalate

sodium nitrite

sodium nitrite

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

B

trans-cyclopentanediol-(1.2)

trans-cyclopentanediol-(1.2)

(+/-)-(trans-2-hydroxy-cyclopentyl)-trimethyl-ammonium; iodide
120640-00-8, 120640-01-9

(+/-)-(trans-2-hydroxy-cyclopentyl)-trimethyl-ammonium; iodide

Ag2O

Ag2O

H2O

H2O

Cyclopentene oxide
285-67-6

Cyclopentene oxide

Conditions
ConditionsYield
Erhitzen des Reaktionsprodukts auf 130grad;
methanol
67-56-1

methanol

(+/-)-(trans-2-hydroxy-cyclopentyl)-trimethyl-ammonium; iodide
120640-00-8, 120640-01-9

(+/-)-(trans-2-hydroxy-cyclopentyl)-trimethyl-ammonium; iodide

Ag2O

Ag2O

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

trans-cyclopentane-1,2-diol
5057-99-8

trans-cyclopentane-1,2-diol

C

trans-2-methoxy-cyclopentanol

trans-2-methoxy-cyclopentanol

Conditions
ConditionsYield
Erhitzen des Reaktionsprodukts bis auf 190grad;
3,3-(α-hydroxytetramethylene)diazirine
334538-40-8

3,3-(α-hydroxytetramethylene)diazirine

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

C

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h; Photolysis;
3,3-(α-hydroxytetramethylene)diazirine lithium salt

3,3-(α-hydroxytetramethylene)diazirine lithium salt

A

Cyclopentene oxide
285-67-6

Cyclopentene oxide

C

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h; Photolysis;
Cyclopentene oxide
285-67-6

Cyclopentene oxide

aniline
62-53-3

aniline

trans-2-(phenylamino)cyclopentanol
77924-49-3, 101593-89-9

trans-2-(phenylamino)cyclopentanol

Conditions
ConditionsYield
With zirconium(IV) chloride at 20℃; for 0.25h;100%
With lithium bromide at 20℃; for 5h;100%
With sulfated zirconia In neat (no solvent) at 20℃; for 0.5h; regioselective reaction;98%
pyrrolidine
123-75-1

pyrrolidine

Cyclopentene oxide
285-67-6

Cyclopentene oxide

(+/-)-trans-(1-pyrrolidinyl)cyclopentan-2-ol
32635-39-5

(+/-)-trans-(1-pyrrolidinyl)cyclopentan-2-ol

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation;100%
With triethylaluminum 1.) toluene, CH2Cl2, 25-30 deg C, 30 min, 2.) room temperature; Yield given. Multistep reaction;
In water
With potassium carbonate
In ethanol at 80℃; for 18h; Inert atmosphere;
Cyclopentene oxide
285-67-6

Cyclopentene oxide

diallylamine
124-02-7

diallylamine

trans-2-(diallylamino)cyclopentanol
77924-51-7

trans-2-(diallylamino)cyclopentanol

Conditions
ConditionsYield
In ethanol for 24h; Heating;100%
In ethanol at 95℃; Sealed tube;100%
With triethylaluminum 1.) toluene, CH2Cl2, 25-30 deg C, 30 min, 2.) room temperature; Yield given. Multistep reaction;
Cyclopentene oxide
285-67-6

Cyclopentene oxide

(+/-)-trans-2-iodocyclopentanol
57857-90-6, 89417-14-1, 116051-23-1, 122673-93-2

(+/-)-trans-2-iodocyclopentanol

Conditions
ConditionsYield
With iodine; tiolacetic acid In dichloromethane at 20℃; for 0.333333h; Ring cleavage;100%
With cerium(III) chloride; sodium iodide In acetonitrile at 20℃; for 0.166667h;91%
With cerium(III) chloride; sodium iodide In acetonitrile at 20℃; for 24h;89.5%
With water; iodine; triphenylphosphine In acetonitrile for 0.25h; Ambient temperature; Yield given;
With water; lithium iodide
Cyclopentene oxide
285-67-6

Cyclopentene oxide

trans-2-aminocyclopentanol
33092-86-3

trans-2-aminocyclopentanol

Conditions
ConditionsYield
With ammonium hydroxide at 85℃; for 0.5h; microwave irradiation;100%
With ammonium hydroxide In ethanol at 120 - 140℃; for 5h; in steel autoclave;71%
With ammonium hydroxide at 140℃; under 15200 Torr;
Cyclopentene oxide
285-67-6

Cyclopentene oxide

cyclopentene
142-29-0

cyclopentene

Conditions
ConditionsYield
With sodium amalgam; chiral Co(II) In tetrahydrofuran-d8 at 20℃; for 6h; deoxygenation;100%
With triphenylphosphine at 200℃; for 8.5h;59%
With trifluoroacetic acid; selenobenzamide In dichloromethane at 20℃; for 30h; Mechanism; With other reagents are dicussed.;85 % Chromat.
piperidine
110-89-4

piperidine

Cyclopentene oxide
285-67-6

Cyclopentene oxide

trans-2-(piperidin-1-yl)cyclopentanol

trans-2-(piperidin-1-yl)cyclopentanol

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation;100%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

4-bromo-3-fluorophenol
121219-03-2

4-bromo-3-fluorophenol

trans-2-(4-bromo-3-fluorophenoxy)cyclopentanol

trans-2-(4-bromo-3-fluorophenoxy)cyclopentanol

Conditions
ConditionsYield
With sodium carbonate In propyl cyanide at 175℃; for 2h; microwave irradiation; Inert atmosphere;100%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

C5H12N2O
158001-05-9

C5H12N2O

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 85℃; for 12h;100%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

(±)-trans-2-azidocyclopentanol

(±)-trans-2-azidocyclopentanol

Conditions
ConditionsYield
With PEG-400; sodium azide at 20℃; for 0.583333h;99%
With 1‑(1‑carboxymethyl)‑3‑methylimidazolium tetrafluoroborate; sodium azide In neat (no solvent) at 60℃; for 0.5h; Reagent/catalyst; Green chemistry; regioselective reaction;95%
With sodium azide; glycerol-tri(3-methylimidazolium) trimesylate In water at 60℃; for 2h;94%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

((1R,2R)-2-Chloro-cyclopentyloxy)-trimethyl-silane
80717-12-0

((1R,2R)-2-Chloro-cyclopentyloxy)-trimethyl-silane

Conditions
ConditionsYield
In chloroform at 25℃; for 0.25h;99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

hex-1-yne
693-02-7

hex-1-yne

trans-2-(hex-1-yn-1-yl)cyclopentan-1-ol

trans-2-(hex-1-yn-1-yl)cyclopentan-1-ol

Conditions
ConditionsYield
Stage #1: hex-1-yne With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: Cyclopentene oxide In tetrahydrofuran at -78℃; for 4h;
99%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h;
Stage #2: Cyclopentene oxide With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 1.3h; Yamaguchi-Hirao alkylation; Further stages.;
62%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

thiobenzoic acid
98-91-9

thiobenzoic acid

(+/-)-thiobenzoic acid S-(trans-2-hydroxy-cyclopentyl ester)
93604-41-2

(+/-)-thiobenzoic acid S-(trans-2-hydroxy-cyclopentyl ester)

Conditions
ConditionsYield
With aluminum oxide In diethyl ether at 20℃; for 1h;99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

morpholine
110-91-8

morpholine

2-(morpholin-4-yl)cyclopentanol
161193-34-6

2-(morpholin-4-yl)cyclopentanol

Conditions
ConditionsYield
With acetic acid In water at 20℃; for 0.5h; Solvent; Reagent/catalyst;99%
In ethanol Heating;
Cyclopentene oxide
285-67-6

Cyclopentene oxide

2-methoxyphenylmagnesium bromide
16750-63-3

2-methoxyphenylmagnesium bromide

2-(2-methoxyphenyl)cyclopentanol
1250244-71-3

2-(2-methoxyphenyl)cyclopentanol

Conditions
ConditionsYield
Stage #1: 2-methoxyphenylmagnesium bromide With copper(l) iodide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: Cyclopentene oxide In tetrahydrofuran at 20℃;
Stage #3: With water; ammonium chloride In tetrahydrofuran at 20℃; for 0.5h;
99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

4,4'-diamino diphenyl methane
101-77-9

4,4'-diamino diphenyl methane

2-(4-(4-(2-hydroxycyclopentylamino)benzyl)phenylamino)cyclopentanol

2-(4-(4-(2-hydroxycyclopentylamino)benzyl)phenylamino)cyclopentanol

Conditions
ConditionsYield
With iron oxide In neat (no solvent) at 20℃; for 20h; Green chemistry; regioselective reaction;99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

phenylacetylene
536-74-3

phenylacetylene

trans-2-(phenylethynyl)cyclopentan-1-ol

trans-2-(phenylethynyl)cyclopentan-1-ol

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: Cyclopentene oxide In tetrahydrofuran at -78℃; for 4h;
99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

trans-2-((4-methoxybenzyl)amino)cyclopentanol

trans-2-((4-methoxybenzyl)amino)cyclopentanol

Conditions
ConditionsYield
With acetic acid In neat (no solvent) at 20℃; for 1h; regioselective reaction;99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

1-bromo-5-dimethoxy-2-vinylbenzene
139469-06-0

1-bromo-5-dimethoxy-2-vinylbenzene

(1R,2S)-2-(4-methoxy-2-vinylphenyl)cyclopentan-1-ol

(1R,2S)-2-(4-methoxy-2-vinylphenyl)cyclopentan-1-ol

Conditions
ConditionsYield
Stage #1: 1-bromo-5-dimethoxy-2-vinylbenzene With iodine; magnesium for 0.5h; Reflux; Inert atmosphere; Sealed tube;
Stage #2: With copper(l) iodide at 0℃; for 0.5h; Inert atmosphere;
Stage #3: Cyclopentene oxide In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;
99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

(+/-)-trans-2-chlorocyclopentanol
20377-80-4

(+/-)-trans-2-chlorocyclopentanol

Conditions
ConditionsYield
With morpholine; 1,3,5-trichloro-2,4,6-triazine In water at 20℃; for 0.25h;98%
With zirconyl chloride In acetonitrile at 20℃; for 0.333333h;98%
With cerium(III) chloride In acetonitrile for 1h; Heating;90%
With hydrogenchloride at -20 - -10℃;
With hydrogenchloride
Cyclopentene oxide
285-67-6

Cyclopentene oxide

ethyl p-tolyl sulfone
7569-34-8

ethyl p-tolyl sulfone

α-(2-hydroxycyclopentyl)ethyl p-tolyl sulfone

α-(2-hydroxycyclopentyl)ethyl p-tolyl sulfone

Conditions
ConditionsYield
With n-butyllithium In hexane; toluene 1.) 60-65 deg C, 1 h, 2.) 110 deg C, 18 h;98%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

phenylmagnesium bromide

phenylmagnesium bromide

trans-2-phenylcyclopentan-1-ol
42086-64-6

trans-2-phenylcyclopentan-1-ol

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran98%
86%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

lithium phenylacetylide
4440-01-1

lithium phenylacetylide

trans-2-(phenylethynyl)cyclopentan-1-ol

trans-2-(phenylethynyl)cyclopentan-1-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at -78℃;98%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

trans-2-phenylcyclopentan-1-ol
42086-64-6

trans-2-phenylcyclopentan-1-ol

Conditions
ConditionsYield
With (lithium)2(CN)(phenyl)2cuprate In tetrahydrofuran for 10h; Ambient temperature;98%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

trans-cyclopentane-1,2-diol
5057-99-8

trans-cyclopentane-1,2-diol

Conditions
ConditionsYield
With water; tetra(n-butyl)ammonium hydrogensulfate at 20 - 45℃;98%
With water at 100℃; for 18h;96%
With carbon tetrabromide at 60℃; for 3.5h;85%
Conditions
ConditionsYield
With dimethylbromosulphonium bromide In acetonitrile at 20℃; for 0.333333h;98%
With quaternary ammonium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; water In acetonitrile for 3h; Heating;80%
With triphenylphosphine hydrobromide In dichloromethane at -90℃; for 0.716667h; Ring cleavage;76%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

2-((S)-1-Phenyl-ethylamino)-cyclopentanol
537688-49-6

2-((S)-1-Phenyl-ethylamino)-cyclopentanol

Conditions
ConditionsYield
With lithium perchlorate In acetonitrile for 18h; Heating;98%
With lithium perchlorate In acetonitrile for 18h; Heating;
Cyclopentene oxide
285-67-6

Cyclopentene oxide

phenylselenyl zinc chloride
1111071-92-1

phenylselenyl zinc chloride

trans-1-hydroxy-2-(phenylseleno)cyclopentane
75826-42-5, 113815-50-2, 124615-81-2

trans-1-hydroxy-2-(phenylseleno)cyclopentane

Conditions
ConditionsYield
In water at 20℃; for 2h;98%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

4-methoxyphenyl magnesium bromide
13139-86-1

4-methoxyphenyl magnesium bromide

2-(4-methoxyphenyl)cyclopentanol
933674-44-3

2-(4-methoxyphenyl)cyclopentanol

Conditions
ConditionsYield
Stage #1: 4-methoxyphenyl magnesium bromide With copper(l) iodide In tetrahydrofuran; diethyl ether at -78℃; for 0.5h;
Stage #2: Cyclopentene oxide In tetrahydrofuran; diethyl ether at -78 - 20℃;
98%

Cyclopentene oxide Chemical Properties

Product Name: Cyclopentene oxide (CAS NO.285-67-6)

Molecular Formula: C5H8O
Molecular Weight: 84.12g/mol
Mol File: 285-67-6.mol
EINECS: 206-005-6
Boiling point: 102 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 10 °C
Density: 1.071 g/cm3
Refractive index: n20/D 1.434(lit.)
Index of Refraction: 1.49 
Molar Refractivity: 22.71 cm3 
Molar Volume: 78.5 cm3 
Surface Tension: 36.9 dyne/cm
Enthalpy of Vaporization: 32.71 kJ/mol
Vapour Pressure: 39.6 mmHg at 25°C
XLogP3-AA: 0.8
H-Bond Donor: 0
H-Bond Acceptor: 1
Structure Descriptors of Cyclopentene oxide (CAS NO.285-67-6):
  IUPAC Name: (1R,5S)-6-oxabicyclo[3.1.0]hexane
  Canonical SMILES: C1CC2C(C1)O2
  Isomeric SMILES: C1C[C@@H]2[C@H](C1)O2
  InChI: InChI=1S/C5H8O/c1-2-4-5(3-1)6-4/h4-5H,1-3H2/t4-,5+ 
  InChIKey: GJEZBVHHZQAEDB-SYDPRGILSA-N
Product Categories: Organics

Cyclopentene oxide Toxicity Data With Reference

1.    

mmo-sat 15 µmol/plate

    MUREAV    Mutation Research. 90 (1981),67.
2.    

mmo-klp 2 mmol/L

    MUREAV    Mutation Research. 89 (1981),269.
3.    

sce-ham:lng 40 mmol/L

    MUREAV    Mutation Research. 249 (1991),55.

Cyclopentene oxide Consensus Reports

Reported in EPA TSCA Inventory.

Cyclopentene oxide Safety Profile

Safety Information of Cyclopentene oxide (CAS NO.285-67-6):
Hazard Codes:F,Xi
Risk Statements:
11:  Highly Flammable
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin 
Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing 
37:  Wear suitable gloves
39:  Wear eye/face protection

Cyclopentene oxide Specification

 Cyclopentene oxide , its CAS NO. is 285-67-6, the synonyms are Cyclopentane, 1,2-epoxy- ; Cyclopentene epoxide ; Epoxycyclopentane ; cis-1,2-Epoxycyclopentane ; 1,2-Epoxycyclopentane ; 6-Oxabicyclo(3.1.0)hexane .

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