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Basic Information
CAS No.: 285-67-6
Name: Cyclopentene oxide
Molecular Structure:
Molecular Structure of 285-67-6 (Cyclopentene oxide)
Formula: C5H8O
Molecular Weight: 84.1179
Synonyms: 1,2-Epoxycyclopentane;Cyclopentane, 1,2-epoxy-;Cyclopentene epoxide;Epoxycyclopentane;NSC 148216;NSC 196230;cis-1,2-Epoxycyclopentane;
EINECS: 206-005-6
Density: 1.071 g/cm3
Melting Point: 136-137 °C
Boiling Point: 102 °C at 760 mmHg
Flash Point: 10 °C
Solubility: Immiscible with water.
Appearance: Clear colorless to very faintly yellow liquid
Hazard Symbols: FlammableF,IrritantXi
Risk Codes: 11-36/37/38
Safety: 16-26-36-36/37/39
Transport Information: UN 1993 3/PG 2
PSA: 12.53000
LogP: 0.93770
Synthetic route
142-29-0

cyclopentene

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%
142-29-0

cyclopentene

A

285-67-6

Cyclopentene oxide

B

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

285-67-6

Cyclopentene oxide

Conditions
ConditionsYield
decompn. at 200°C for 0.5 h;86%
62820-00-2

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

142-29-0

cyclopentene

A

285-67-6

Cyclopentene oxide

B

4714-62-9

4-cyano-N-methylaniline

C

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

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%
5057-99-8

trans-cyclopentane-1,2-diol

285-67-6

Cyclopentene oxide

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

tert.-butylhydroperoxide

142-29-0

cyclopentene

A

285-67-6

Cyclopentene oxide

B

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%
142-29-0

cyclopentene

A

285-67-6

Cyclopentene oxide

B

4065-92-3

cyclopentane-1,2-diol

C

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%
142-29-0

cyclopentene

A

285-67-6

Cyclopentene oxide

C

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.
142-29-0

cyclopentene

A

285-67-6

Cyclopentene oxide

B

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.
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Chemistry

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

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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

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 .