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Cyclopentanone

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Cyclopentanone

EINECS 204-435-9
CAS No. 120-92-3 Density 0.987 g/cm3
PSA 17.07000 LogP 1.12950
Solubility practically insoluble in water Melting Point -51 °C
Formula C5H8O Boiling Point 130.457 °C at 760 mmHg
Molecular Weight 84.1179 Flash Point 30.556 °C
Transport Information UN 2245 3/PG 3 Appearance colourless liquid
Safety 23 Risk Codes 10-36/38
Molecular Structure Molecular Structure of 120-92-3 (Cyclopentanone) Hazard Symbols IrritantXi
Synonyms

Adipicketone;Adipin keton;Dumasin;Ketocyclopentane;Ketopentamethylene;NSC 4122;

Article Data 679

Cyclopentanone Synthetic route

96-41-3

Cyclopentanol

120-92-3

cyclopentanone

Conditions
ConditionsYield
With water; nickel dibromide; dibenzoyl peroxide In N,N-dimethyl acetamide at 60℃; for 3h;100%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) In hexane for 20h; Solvent; Reflux;100%
With allyl methyl carbonate; dihydridotetrakis(triphenylphosphine)ruthenium In toluene at 100℃; for 13h;99%
142-29-0

cyclopentene

120-92-3

cyclopentanone

Conditions
ConditionsYield
With oxygen; palladium(II) sulfate; PdSO4-H3PMo6W6O40 In cyclohexane; water at 30℃; for 6h;100%
With oxygen; H3PMo6W6O40 In cyclohexane; water at 29.9℃; under 760 Torr; for 6h;100%
With palladium(II) sulfate; oxygen; H3PMo6W6O40 In cyclohexane; water at 29.9℃; under 760 Torr; for 6h; Product distribution; Rate constant; other time, other Pd(II) salt, other concentration of catalyst;100%
930-30-3

cyclopent-2-enone

120-92-3

cyclopentanone

Conditions
ConditionsYield
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%
1192-28-5

Cyclopentanone oxime

120-92-3

cyclopentanone

Conditions
ConditionsYield
With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 In acetonitrile for 0.0583333h; Oxidation; Heating;100%
With potassium permanganate In water; acetonitrile at 25℃; for 1h;96%
With dihydrogen peroxide; tripropylammonium fluorochromate (VI) In acetone at 0 - 10℃; for 2.5h;96%

Sodium; 6-cyclopentylideneamino-hexanoate

120-92-3

cyclopentanone

Conditions
ConditionsYield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;100%
137-43-9

Cyclopentyl bromide

120-92-3

cyclopentanone

Conditions
ConditionsYield
With oxygen; kieselguhr; copper(l) chloride In hexane for 2.5h; Oxidation; Heating;99%
85895-34-7

1,1-Bis(phenylthio)cyclopentane

120-92-3

cyclopentanone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20 - 25℃; for 2h; Irradiation;98%
98-01-1

furfural

120-92-3

cyclopentanone

Conditions
ConditionsYield
With hydrogen In water at 160℃; under 30003 Torr; for 7h; Automated synthesizer;98%
With hydrogen In water at 160℃; under 30003 Torr; for 2.5h; Reagent/catalyst; Temperature; Pressure; Autoclave;96%
With hydrogen In water at 150℃; under 30003 Torr; for 6h; Reagent/catalyst; Autoclave;95%
287-92-3

Cyclopentane

120-92-3

cyclopentanone

Conditions
ConditionsYield
With hydrogenchloride; FeH6Mo6O24(3-)*3H3N*3H(1+)*7H2O; tetrabutylammomium bromide; dihydrogen peroxide In 1,4-dioxane; water at 85℃; for 24h;96%
With [Fe4III(μ-O)2(μ-acetate)6(2,2'-bipyridine)2(H2O)2](NO3-)(OH-); dihydrogen peroxide; acetic acid In water; acetonitrile at 32℃; for 3h; Catalytic behavior;60%
With dihydrogen peroxide; vanadium phosphorus oxide In acetonitrile at 50℃; for 20h;48%
2562-38-1

nitrocyclopentane

120-92-3

cyclopentanone

Conditions
ConditionsYield
With sodium perborate at 70℃; for 3h; Ionic liquid;95%
With bis-trimethylsilanyl peroxide; sodium hydride In tetrahydrofuran at 20℃; for 24h; Hydrolysis;65%

Cyclopentanone Specification

The Cyclopentanone, with the CAS registry number 120-92-3 and EINECS registry number 204-435-9, is a clear colorless liquid with a petroleum-like odor. It belongs to the following product categories: Pharmaceutical Intermediates; Organics; Alpha Sort; C; Volatiles/ Semivolatiles; C3 to C6; Carbonyl Compounds; Ketones; Alphabetical Listings; C-D; Flavors and Fragrances. And the molecular formula of the chemical is C5H8O. What's more, it is commonly used as a thinner for various epoxies used in MEMS fabrication, such as SU-8.

The physical properties of Cyclopentanone are as followings: (1)ACD/LogP: 0.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.293; (4)ACD/LogD (pH 7.4): 0.293; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.405; (8)ACD/KOC (pH 7.4): 34.405; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 17.07 Å2; (13)Index of Refraction: 1.457; (14)Molar Refractivity: 23.189 cm3; (15)Molar Volume: 85.214 cm3; (16)Polarizability: 9.193×10-24cm3; (17)Surface Tension: 34.01 dyne/cm; (18)Density: 0.987 g/cm3; (19)Flash Point: 30.556 °C; (20)Enthalpy of Vaporization: 36.35 kJ/mol; (21)Boiling Point: 130.457 °C at 760 mmHg; (22)Vapour Pressure: 9.702 mmHg at 25°C.

Preparation of Cyclopentanone: This chemical can be prepared by adipate in the presence of baryta with heating.

Uses of Cyclopentanone: It can react with pyrrolidine to produce 1-cyclopent-1-enyl-pyrrolidine. This reaction will need reagent methyl iodide and bis(trimethylsilyl)acetamide, and the menstruum petroleum ether. The reaction time is 1.5 hours with temperature of 40-50°C, and the yield is about 82%. 

You should be cautious while dealing with this chemical. It is a kind of flammble chemical which irritates to eyes and skin. Therefore, you had better not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).  

You can still convert the following datas into molecular structure:
(1)SMILES: C1CCC(=O)C1
(2)InChI: InChI=1/C5H8O/c6-5-3-1-2-4-5/h1-4H2
(3)InChIKey: BGTOWKSIORTVQH-UHFFFAOYAP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo subcutaneous 3gm/kg (3000mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903.
mammal (species unspecified) LD50 oral 2gm/kg (2000mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mouse LD50 intraperitoneal 1950mg/kg (1950mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA
Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 254, Pg. 2245, 1962.
mouse LDLo subcutaneous 2600mg/kg (2600mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: COMA

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903.
rat LC50 inhalation 19500mg/m3 (19500mg/m3) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LIVER: OTHER CHANGES
National Technical Information Service. Vol. OTS0572861,

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