Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
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% |
Conditions | Yield |
---|---|
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% |
cyclopentanone
Conditions | Yield |
---|---|
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde; | 100% |
Conditions | Yield |
---|---|
With oxygen; kieselguhr; copper(l) chloride In hexane for 2.5h; Oxidation; Heating; | 99% |
1,1-Bis(phenylthio)cyclopentane
cyclopentanone
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20 - 25℃; for 2h; Irradiation; | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium perborate at 70℃; for 3h; Ionic liquid; | 95% |
With bis-trimethylsilanyl peroxide; sodium hydride In tetrahydrofuran at 20℃; for 24h; Hydrolysis; | 65% |
1-Methanesulfonyl-1-methylsulfanyl-cyclopentane
cyclopentanone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 3h; Heating; | 94% |
Conditions | Yield |
---|---|
With Glyoxilic acid; Amberlyst 15 for 0.05h; microwave irradiation; | 94% |
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃; for 3h; | 88% |
Adipic acid
6-Hydroxyhexanoic acid
A
hexahydro-2H-oxepin-2-one
B
cyclopentanone
Conditions | Yield |
---|---|
at 280 - 300℃; Product distribution / selectivity; | A 7% B 94% |
sodium phosphate at 290℃; Product distribution / selectivity; | A 0.3% B 77% |
tin(IV) oxide at 270℃; Product distribution / selectivity; | A 1% B 73% |
sodium hydroxide at 270 - 290℃; Product distribution / selectivity; | A 25% B 58% |
sodium borate at 290℃; Product distribution / selectivity; | A 0.3% B 39% |
Conditions | Yield |
---|---|
Al2O3#dotK2O In water at 360℃; under 0.750075 Torr; for 500h; | 93% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide for 10h; Ambient temperature; | A 8% B 92% |
Conditions | Yield |
---|---|
With tetrabutylammonium tricarbonylnitrosylferrate In hexane at 20 - 80℃; Molecular sieve; Inert atmosphere; | A 92% B n/a |
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide In acetonitrile at 50℃; for 3h; the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C; | A n/a B 91.6% |
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% |
Conditions | Yield |
---|---|
With formaldehyd; silica gel; iron(III) chloride at 20℃; for 0.0833333h; | 90% |
With chloral hydrate In hexane at 25℃; for 0.5h; Solvent; Temperature; Inert atmosphere; | 83% |
With boron trifluoride diethyl etherate; sodium iodide In acetonitrile for 2h; Heating; | 82% |
With water; β‐cyclodextrin at 20℃; for 16h; | 98 % Chromat. |
2-cyclopentylidene-1,1-dimethylhydrazine
cyclopentanone
Conditions | Yield |
---|---|
With cerium(III) chloride; silica gel for 0.0666667h; Microwave irradiation; | 90% |
With sodium perborate; sodium hydroxide; potassium dihydrogenphosphate; water In tert-butyl alcohol at 60℃; for 24h; | 70% |
With ferric nitrate In dichloromethane 30 min., r.t., then reflux; | 69% |
With silica gel In tetrahydrofuran; water at 25℃; for 10h; | 20% |
Conditions | Yield |
---|---|
With silica gel; iron(III) chloride at 20℃; for 0.333333h; | 90% |
With sulfuric acid In water at 25℃; Rate constant; |
Conditions | Yield |
---|---|
With zirconium hydrogen sulfate; silica gel In hexane for 1.5h; Heating; | 90% |
B
cyclopentanone
Conditions | Yield |
---|---|
With CO In toluene toluene soln. of Mo complex placed in autoclave under 50 atm CO pressure, stirred at 90°C for 12 h; distn., trapping at -78°C; | A 83% B 90% |
cyclopentanone
Conditions | Yield |
---|---|
decompn. at 150°C for 0.5 h; | 88% |
decompn. at 150°C for 0.5 h; | 88% |
Conditions | Yield |
---|---|
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h; | A 87.4% B 0.8% |
1-pyrrolidinocyclopent-1-ene
2-((trifluoromethyl)thio)isoindoline-1,3-dione
A
cyclopentanone
Conditions | Yield |
---|---|
In acetonitrile at 25℃; for 48h; Hydrolysis; trifluoromethylthiolation; | A 12.9% B 87.1% |
Conditions | Yield |
---|---|
With water; oxygen; lithium bromide; copper(ll) bromide In tetrahydrofuran at 25℃; under 760.051 Torr; | A 87% B n/a |
Conditions | Yield |
---|---|
With iodo trichloro silane for 1h; Ambient temperature; | A 86% B 39% |
Conditions | Yield |
---|---|
With pyrographite at 450℃; for 0.5h; | 85% |
With calcium hydroxide at 350℃; Product distribution; Further Variations:; Reagents; | 84.2% |
at 290℃; |
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry; | 85% |
With oxygen; potassium iodide; sodium nitrite In water; acetonitrile for 8h; Reflux; | 75% |
With potassium hydroxide In ethyl acetate at -78℃; Product distribution; | 18% |
2-aminoacetophenone
cyclopentanone
9-methyl-2,3-dihydro-1H-cyclopenta[b]quinoline
Conditions | Yield |
---|---|
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate; N,N-dimethyl-formamide at 90℃; Friedlaender reaction; | 98% |
With ammonium cerium (IV) nitrate In ethanol for 16h; Friedlaender synthesis; Reflux; | 97% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 20℃; Aldol Condensation; | 100% |
With molybdenum(V) chloride In neat (no solvent) for 0.0416667h; Claisen-Schmidt Condensation; Microwave irradiation; Green chemistry; | 99% |
With potassium hydroxide In ethanol at 40℃; for 0.00138889h; | 98% |
4-methoxy-benzaldehyde
cyclopentanone
(2E,5E)-2,5-bis(4-methoxybenzylidene)cyclopentanone
Conditions | Yield |
---|---|
With lithium perchlorate; triethylamine at 20℃; for 0.0166667h; | 100% |
With trichloro(trifluoromethanesulfonato)titanium(IV) at 20℃; for 2h; aldol condensation; | 97% |
With animal bone meal catalyst modified with Na In water for 0.25h; Reflux; | 97% |
cyclopentanone
ethyl 2-cyanoacetate
ethyl 2-cyano-2-cyclopentylideneacetate
Conditions | Yield |
---|---|
piperidine at 23℃; under 750.06 Torr; for 2h; Knoevenagel condensation; | 100% |
With morpholine; bis(acetylacetonate)oxovanadium at 40℃; for 1h; Reagent/catalyst; Temperature; Time; Knoevenagel Condensation; | 99% |
With ammonium acetate; acetic acid In toluene Knoevenagel Condensation; Reflux; | 93% |
Conditions | Yield |
---|---|
With iodine; mercury dichloride In dichloromethane for 1h; Ambient temperature; | 100% |
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.5h; | 91% |
With N-chloro-succinimide In dimethyl sulfoxide at 20℃; for 0.25h; | 87% |
Conditions | Yield |
---|---|
With N,O-bis(trimethylsilyl)hydroxylamine; potassium hydride In tetrahydrofuran for 1.5h; Ambient temperature; - 78 deg C to room temp.; | 100% |
With sodium hydroxide; hydroxylamine hydrochloride at 20℃; for 0.5h; grinding; | 100% |
With hydroxylamine hydrochloride; sodium acetate In methanol Heating; | 100% |
Conditions | Yield |
---|---|
With zirconium dioxide hydrate; isopropyl alcohol at 130℃; for 0.666667h; Meerwein-Ponndorf-Verley Reduction; | 100% |
Stage #1: cyclopentanone With tetrabutylammonium tricarbonylnitrosylferrate; tricyclohexylphosphine In 1,4-dioxane at 50℃; Inert atmosphere; Stage #2: With water; sodium hydroxide In 1,4-dioxane; methanol at 20℃; for 1.5h; Inert atmosphere; chemoselective reaction; | 99% |
With C15H18BF3; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 75℃; under 75007.5 Torr; for 20h; Glovebox; | 99% |
chloro-trimethyl-silane
cyclopentanone
1-(trimethylsilyloxy)cyclopentene
Conditions | Yield |
---|---|
With triethylamine; sodium iodide In acetonitrile at 23℃; for 1.5h; Inert atmosphere; | 100% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 40℃; for 0.5h; | 98% |
With magnesium In N,N-dimethyl-formamide at 15 - 25℃; | 94% |
4-penten-1-ylmagnesium bromide
cyclopentanone
1-(pent-4'-enyl)cyclopentan-1-ol
Conditions | Yield |
---|---|
100% | |
at 0℃; | 90% |
In diethyl ether for 2h; Ambient temperature; | 72% |
nitromethane
cyclopentanone
phenylmethanethiol
1-benzylthio-1-nitromethylcyclopentane
Conditions | Yield |
---|---|
With piperidine In benzene | 100% |
With piperidine In acetonitrile for 4h; Heating; | 94% |
With piperidine In benzene Heating; |
benzoic acid hydrazide
cyclopentanone
N'-cyclopentylidene benzohydrazide
Conditions | Yield |
---|---|
at 143℃; under 2100.21 Torr; for 0.05h; Microwave irradiation; neat (no solvent); | 100% |
for 0.05h; Microwave irradiation; | 100% |
at 20℃; for 0.05h; Microwave irradiation; | 100% |
3,4-dimethoxy-benzaldehyde
cyclopentanone
2,5-Bis<(3,4-dimethoxyphenyl)methylen>cyclopentanon
Conditions | Yield |
---|---|
With lithium perchlorate; triethylamine at 20℃; for 96h; | 100% |
With hydrogenchloride; acetic acid at 25 - 30℃; for 2h; | 85% |
With hydrogenchloride In acetic acid at 25 - 30℃; for 2h; | 85% |
Conditions | Yield |
---|---|
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; | 100% |
With zinc; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran for 0.0833333h; Ambient temperature; | 98% |
With ammonium chloride; zinc In tetrahydrofuran; water at 20℃; for 10h; | 90% |
Conditions | Yield |
---|---|
With trimethyl orthoformate at 40℃; under 6000480 Torr; for 8h; | 100% |
Irradiation; | 25% |
Ce(3+)-mont at 25℃; for 0.5h; Yield given; |
t-butoxycarbonylhydrazine
cyclopentanone
tert-butyl 2-cyclopentylidenehydrazine carboxylate
Conditions | Yield |
---|---|
In methanol at 20℃; for 2h; | 100% |
In methanol at 20℃; for 3h; Inert atmosphere; | 98% |
In hexane for 0.333333h; Heating; | 96% |
Conditions | Yield |
---|---|
With iodine; magnesium In diethyl ether for 3h; Grignard reaction; Heating; | 100% |
With iodine; magnesium 1.) ether, reflux, 2.) ether, benzene, RT, 2 h; Yield given. Multistep reaction; | |
Stage #1: 1-Bromonaphthalene With magnesium In diethyl ether Stage #2: cyclopentanone In diethyl ether for 3h; Grignard reaction; | |
Stage #1: 1-Bromonaphthalene With magnesium In diethyl ether for 0.5h; Reflux; Stage #2: cyclopentanone In diethyl ether at 0℃; for 1h; |
2,4,6-trimethylbenzenesulfonohydrazide
cyclopentanone
N'-cyclopentylidene-2,4,6-trimethylbenzenesulfonohydrazide
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
In methanol 1.) 50 deg, 2.) room temperature; | 88% |
t-butyldimethylsiyl triflate
cyclopentanone
1-tert-butyldimethylsilyloxycyclopentene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.0833333h; | 100% |
With 2,6-dimethylpyridine In tetrahydrofuran at 0℃; for 1h; | 71% |
With triethylamine In dichloromethane at 0℃; |
ethyl hydrogen (5,6-dihydro-p-dioxin-2-yl)ethylphosphonite
cyclopentanone
Conditions | Yield |
---|---|
for 600h; Ambient temperature; | 100% |
cyclopentanone
1,2-diamino-benzene
2,3-cyclopentano-3,4-dihydro-5H-4-spirocyclopentano-1,5-benzodiazepine
Conditions | Yield |
---|---|
With mesoporous aluminosilicate MCM-41(14) at 100℃; for 1h; | 100% |
With ytterbium(III) triflate at 20℃; for 4h; | 99% |
With octadecafluorodecahydronaphthalene (cis+trans) at 60℃; for 2h; | 99% |
cyclopentanone
toluene-4-sulfonic acid hydrazide
cyclopentanone p-tolylsulfonylhydrazone
Conditions | Yield |
---|---|
In ethanol at 100℃; for 1h; | 100% |
In ethanol at 100℃; for 1.66667h; Inert atmosphere; | 100% |
In methanol at 20℃; Inert atmosphere; | 99.5% |
cyclopentanone
2-amino-1-benzylamine
3',4'-dihydro-1'H-spiro[cyclopentane-1,2'-quinazoline]
Conditions | Yield |
---|---|
In chloroform at 60℃; for 24h; | 100% |
With acetic acid In ethanol for 3h; Heating; | 82% |
cyclopentanone
4-flourophenylmagnesium bromide
1-cyclopent-1-enyl 4-fluorobenzene
Conditions | Yield |
---|---|
Stage #1: cyclopentanone; 4-flourophenylmagnesium bromide In tetrahydrofuran at 0℃; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water | 100% |
In tetrahydrofuran; diethyl ether at 0℃; for 2h; Reflux; | 100% |
Stage #1: cyclopentanone; 4-flourophenylmagnesium bromide In tetrahydrofuran at 0℃; for 2h; Reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran Cooling with ice; | 100% |
In diethyl ether Grignard reaction; Reflux; | 61% |
(i), (ii) KHSO4; Multistep reaction; |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 0.0166667h; microwave irradiation; | 100% |
With aluminum oxide; potassium fluoride In methanol at 35 - 40℃; for 0.5h; Claisen-Schmidt condensation; ultrasound irradiation; | 96% |
With sodium-modified hydroxyapatite In water for 0.5h; Aldol condensation; Reflux; | 96% |
nitromethane
thiophenol
cyclopentanone
1-nitromethyl-1-phenylthiocyclopentane
Conditions | Yield |
---|---|
With piperidine In benzene for 61h; Heating; | 100% |
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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