Conditions | Yield |
---|---|
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. |
A
Cyclopentyl bromide
B
thianthrene-5-oxide
C
cyclopentene
D
Thianthrene
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium bromide Product distribution; Substitution; elimination; | A 89% B 100% C 1.5% D 3.5% |
Conditions | Yield |
---|---|
With hydrogen; palladium In methanol at 30℃; under 760 Torr; Rate constant; Product distribution; Thermodynamic data; mechanism of reaction, var. solvents, var. amount of catalyst, var. catalysts, var. conc., var. pressure, eq. constants, activation energy; | 97.1% |
With hydrogen; Ruthenium deposition on Pd/Cu at 199.9℃; Rate constant; effect of catalyst content on the rate on the yield; | 3% |
With hydrogen; ruthenium at 49.9℃; under 140 Torr; Product distribution; variation of temperature; |
C17H17N3O8S2
A
(4-nitro-N-((4-nitrophenyl)sulfonyl)benzenesulfonamide)
B
cyclopentene
Conditions | Yield |
---|---|
In neat (no solvent) at 175℃; for 0.5h; | A 95% B 90% |
Conditions | Yield |
---|---|
tert-butylhydroquinone In diphenylether at 215℃; for 2.58333h; Product distribution / selectivity; | 94.19% |
Conditions | Yield |
---|---|
With nickel(II) oxide; 1-methyl-2-nitrobenzene; oxalic acid at 280 - 310℃; for 3.16667h; Temperature; | 92% |
With 5,6,8,9-tetrahydro-7-phenyldibenzoxanthenylium tetrafluoroborate In dichloromethane at 20℃; for 27h; |
Conditions | Yield |
---|---|
With formic acid at 20 - 240℃; Inert atmosphere; | 86% |
cyclopentene
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; pentane 1.) -78 deg C; 2.) 25 deg C over 1 h; | 85% |
With n-butyllithium | 85% |
Conditions | Yield |
---|---|
With [i-PrNDI]Ni2(C6H6); 1,3,5-trimethyl-benzene In benzene for 24h; Reagent/catalyst; Inert atmosphere; Glovebox; regioselective reaction; | 83% |
at 526.9℃; Rate constant; pyrolysis, other temperature; | |
at 341.2℃; under 485 - 500 Torr; Rate constant; Mechanism; | |
at 303.9 - 780.9℃; Kinetics; |
n-decyl acetate
A
1-hexene
B
1-Decene
C
1,2-dimethylcyclopentane
D
1-Butyl-2-methylcyclopropane
E
1-Methyl-2-pentylcyclopropane
F
cyclopentene
Conditions | Yield |
---|---|
at 495℃; for 0.00727778h; Rate constant; Product distribution; various temp., also in toluene, also with 14C-labelled ester; | A 1.03% B 81.3% C 1.91% D 1.2% E 0.497% F 0.45% |
Conditions | Yield |
---|---|
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane 1.) 0 deg C; 2.) rt., 3h; | A 80% B n/a |
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane 1.) 0 deg C; 2.)rt., 3h; | |
With bismuth(III) chloride In tetrachloromethane for 1.5h; Heating; |
Conditions | Yield |
---|---|
at 178℃; under 200 Torr; Mechanism; | 78% |
A
thianthrene-5-oxide
B
cyclopentyl iodide
C
cyclopentene
D
Thianthrene
Conditions | Yield |
---|---|
With potassium iodide In acetonitrile for 2h; Product distribution; Substitution; elimination; | A 78% B 55% C 21% D 19% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 70℃; for 72h; Glovebox; | A 75% B n/a C n/a |
Conditions | Yield |
---|---|
With tetra-n-propylammonium bromide In N,N-dimethyl-formamide electrolytic reduction: platinum electrodes; reference: Ag wire. cathode and anode separated by a membrane; | A 71% B 15% |
2-(cyclopentyloxy)tropone
A
2-hydroxy-2,4,6-cycloheptatrien-1-one
B
cyclopentene
Conditions | Yield |
---|---|
In dimethylsulfoxide-d6 at 180℃; for 2h; | A n/a B 70% |
In dimethyl sulfoxide at 180℃; for 8h; |
Conditions | Yield |
---|---|
With hydrogen sulfide at 600℃; | A 12% B 59% |
With silica-supported tetrakis(triphenylphosphite)platinum(0)-derived nanocatalyst In benzene at 600℃; | A 58.1% B 2.2% |
penta-1,3-diene
A
Cyclopentane
B
cyclopenta-1,3-diene
C
cyclopentene
Conditions | Yield |
---|---|
With silica-supported tetrakis(triphenylphosphine)platinum(0)-derived nanocatalyst In benzene at 600℃; | A 0.1% B 53.6% C 4.7% |
Cyclopentyl bromide
A
Cyclopentane
B
bicyclopentyl
C
cyclopentene
D
cyclopentylmagnesium bromide
Conditions | Yield |
---|---|
With magnesium In diethyl ether at 0℃; Mechanism; Rate constant; reaction rate dependence on angular velocity of disk, solution viscosity; | A 13 % Chromat. B 21 % Chromat. C 13 % Chromat. D 50% |
cyclopentyl chloride
water-d2
A
monodeuterocyclopentane
B
cyclopentene
Conditions | Yield |
---|---|
Stage #1: cyclopentyl chloride With magnesium In tetrahydrofuran for 1h; Reflux; Inert atmosphere; Stage #2: water-d2 In tetrahydrofuran at 0℃; Inert atmosphere; | A 50% B n/a |
pentane
A
methylbutane
B
hexane
C
Cyclopentane
D
cyclopenta-1,3-diene
E
cyclopentene
F
benzene
Conditions | Yield |
---|---|
With hydrogen; Platinum-copper at 334.9℃; Product distribution; various temp. and percent Pt; | A 1% B n/a C 49.2% D 25.9% E 15.1% F n/a G n/a |
cyclopentylmagnesium bromide
A
Cyclopentane
B
bicyclopentyl
C
cyclopentene
Conditions | Yield |
---|---|
With copper dichloride In diethyl ether at 0℃; | A 46% B 1% C 42% |
Conditions | Yield |
---|---|
With hydrogen; silica gel; palladium at 330℃; | A n/a B 45% |
With hydrogen; silica gel; palladium at 330℃; | A 40% B n/a |
endo-1,4-Dimethyl-2,3,9-trioxatricyclo<4.2.1.15,8>decane
A
1-(cyclopent-3-en-1-yl)ethanone
B
cis-1,3-Diacetylcyclopentane
C
acetic anhydride
D
acetic acid
E
cyclopentene
Conditions | Yield |
---|---|
In chloroform-d1 at 55℃; for 40h; Mechanism; | A 28% B 32% C 4% D 33% E 2% |
In pentane at -20℃; for 7.5h; Mechanism; Irradiation; | A 23% B 8% C 4% D 25% E 3% |
cis-1,2-cyclopentanediol
A
Cyclopentane
trans-cyclopentane-1,2-diol
C
cyclopentene
Conditions | Yield |
---|---|
With hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 24h; | A 32% B 11% C 6% |
Cyclopentene oxide
A
Cyclopentanol
B
(+)-(R)-2-cyclopentene-1-ol
C
(-)-(S)-2-cyclopenten-1-ol
D
cyclopentanone
E
cyclopentene
Conditions | Yield |
---|---|
With ammonium chloride; hydroxocobalamine hydrochloride; zinc In methanol for 96h; Product distribution; Equilibrium constant; Kinetics; Ambient temperature; dark, isomerization, different solvents (also deuterated ones), different temperatures, ΔH(excit.), ΔS(excit.); | A 0.5% B n/a C n/a D 5.5% E 30% |
isobutene
A
1-butylene
B
(Z)-2-Butene
C
2-methyl-but-2-ene
D
Z-piperylene
E
1-methylbuta-1,3-diene
F
propene
G
methane
H
trans-2-Butene
I
(Z)-pent-2-ene
J
(E)-pent-2-ene
K
ethane
L
propane
M
Isobutane
N
methylbutane
O
ethene
P
1-penten
Q
Cyclopentane
R
2-Methyl-1-butene
S
3-Methyl-1-butene
T
cyclopentene
U
n-butane
V
pentane
Conditions | Yield |
---|---|
CBV1502 at 579.84℃; under 900.09 Torr; Product distribution / selectivity; | A 2.6% B 2.4% C 1.29% D 0.05% E 0.03% F 24.95% G 0.73% H 3.19% I 0.32% J 0.58% K 0.36% L 2.08% M 2.15% N 0.34% O 9.61% P 0.23% Q 0.4% R 0.71% S 0.14% T 0.14% U 1.8% V 0.16% |
CBV28014 at 509.84℃; under 900.09 Torr; Product distribution / selectivity; | A 6.71% B 7.3% C 5.62% D 0.02% E 0.03% F 23.29% G 0.09% H 9.97% I 1.1% J 2.06% K 0.07% L 1.24% M 1.95% N 0.59% O 3.25% P 0.7% Q 0.31% R 2.72% S 0.47% T 0.21% U 1.37% V 0.26% |
Conditions | Yield |
---|---|
With silica-supported tetrakis(triphenylphosphine)platinum(0)-derived nanocatalyst In benzene at 600℃; | A 0.3% B 21.4% C 2.7% |
With silica-supported tetrakis(triphenylphosphite)platinum(0)-derived nanocatalyst In benzene at 600℃; | A 2.1% B 6% C 1.2% |
With platinum on alumina In water at 600℃; | A 0.1% B 1.4% C 0.1% |
With hydrogen at 575℃; under 3087.28 Torr; for 15h; Overall yield = 32 percent; |
1,4-Pentadiene
A
1-methylbuta-1,3-diene
B
ethenylcyclopropane
C
cyclopenta-1,3-diene
D
buta-1,3-diene
E
cyclopentene
Conditions | Yield |
---|---|
Product distribution; Mechanism; Plasmolysis (40 W, 3.48mmol/min, 13.56 MHz); | A n/a B 5% C 21% D n/a E 18% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With zinc(II) tetrahydroborate; dihydrogen peroxide In acetonitrile for 0.166667h; Mechanism; Ambient temperature; | 100% |
With zinc(II) tetrahydroborate; dihydrogen peroxide In acetonitrile for 0.166667h; Ambient temperature; | 100% |
With lithium borohydride; alkaline H2O2; ethyl acetate | 94% |
Conditions | Yield |
---|---|
With n-butyllithium; potassium 2-methylbutan-2-olate In hexane 1) r.t., 14 h, 2) reflux, 5 h; | 100% |
at 850℃; Erhitzen unter vermindertem Druck; | |
With chromium (III)-oxide-aluminium oxide contacts at 450 - 500℃; | |
With palladium at 180 - 200℃; |
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 N-Bromosuccinimide at 0℃; for 1h; | 100% |
With N-Bromosuccinimide In dichloromethane 1.) -20 deg C, 2 h, 2.) 15 deg C; | 70% |
Conditions | Yield |
---|---|
With dibenzoyl peroxide at 90℃; for 10h; | 100% |
methyl (2E)-3-bromoacrylate
cyclopentene
3-Cyclopent-2-en-(Z)-ylidene-propionic acid methyl ester
Conditions | Yield |
---|---|
With palladium diacetate; tetrabutyl-ammonium chloride; potassium acetate In N,N-dimethyl-formamide at 25℃; for 24h; | 100% |
cyclopentene
Conditions | Yield |
---|---|
With sodium azide; Iodine monochloride In acetonitrile 1.) -20 deg C, 30 min; 2.) up to RT, 10 h; | 100% |
With sodium azide; iodine In tetrahydrofuran; methanol; water at 20 - 25℃; for 3h; | 74% |
cyclopentene
4-Aza-2-oxo-1-oxaspiro<5.4>dec-3-ene 4-oxide
Conditions | Yield |
---|---|
at 30℃; under 6000480 Torr; for 48h; | 100% |
cyclopentene
(5R,6S,9R)-6-isopropyl-9-methyl-2-oxo-4-aza-1-oxaspiro[5.4]dec-3-ene 4-oxide
(3R,5aR,8aR,8bS,1'R,4'S)-1-oxo-1,5a,8a,8b-tetrahydrocyclopent[f]isoxazolo[2,3-c]oxazole-3-spiro-3'-menthane
Conditions | Yield |
---|---|
at 30℃; under 6000480 Torr; for 72h; | 100% |
(2,6-(C6H3But)2pyridine)Au(CF3CO2)
tris(pentafluorophenyl)borate
cyclopentene
[(2,6-bis(4-tBuC6H3)2pyridine dianion)Au(eta2-cyclopentene)][CF3COOB(C6F5)4]
Conditions | Yield |
---|---|
In dichloromethane-d2 at -78 - -40℃; | 100% |
Conditions | Yield |
---|---|
With C55H88ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 3h; Reagent/catalyst; Time; | 100% |
Conditions | Yield |
---|---|
With iodine In dichloromethane; water at 20℃; | 100% |
cyclopentene
Conditions | Yield |
---|---|
With selenium(II) chloride In dichloromethane at -78 - 20℃; for 5h; stereoselective reaction; | 100% |
cyclopentene
Conditions | Yield |
---|---|
With selenium dibromide In dichloromethane at -78 - 20℃; for 5h; stereoselective reaction; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
In not given | 99.5% |
In not given | 99.5% |
Conditions | Yield |
---|---|
With 0.42C23H20N4O4*2Cl(1-)*Zn(2+)*10.16H2O*0.58Pd(2+)*0.58C23H20N4O4(1-); hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 1h; | 99% |
With C22H34FeO2Si4; hydrogen In toluene at 20℃; for 6h; Inert atmosphere; Schlenk technique; | 99% |
With C40H56FeN2Si4(2-); hydrogen In 1,2-dimethoxyethane at 80℃; under 7600.51 Torr; for 2h; Schlenk technique; Autoclave; | 99% |
Conditions | Yield |
---|---|
With 1H-imidazole; sodium periodate; MnCl-TPP-(PEO750)4 In water; acetonitrile at 20℃; for 24h; | 99% |
With W-MCM41; dihydrogen peroxide In tert-butyl alcohol at 35℃; for 24h; | 71% |
With sodium periodate; water In 1,2-dichloro-ethane at 20℃; for 1h; | 70.9% |
Conditions | Yield |
---|---|
Stage #1: cyclopentene With bis(1,5-cyclooctadiene)diiridium(I) dichloride; bis(pinacol)diborane at 60℃; for 16h; Inert atmosphere; Stage #2: iodobenzene With palladium diacetate; triphenylphosphine; barium(II) hydroxide In tetrahydrofuran; water at 50℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere; regioselective reaction; | 99% |
at 20℃; Irradiation; |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; potassium acetate; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 24h; | 99% |
tert-butyl 4-nitrobenzoperoxoate
cyclopentene
cyclopent-2-en-1-yl 4-nitrobenzoate
Conditions | Yield |
---|---|
Stage #1: cyclopentene With copper-boron encapsulated with (3-aminopropyl)trimethoxysilane grafted SBA-15 In acetonitrile at 25℃; for 0.5h; Stage #2: tert-butyl 4-nitrobenzoperoxoate In acetonitrile at 25℃; for 50h; Reagent/catalyst; | 99% |
With copper(I) triflate In acetonitrile at 20℃; for 13h; Reagent/catalyst; Sealed tube; Schlenk technique; Inert atmosphere; | 90% |
With Cu(CH3CN)4PF6 immobilized on halloysite, functionalized with ionic liquid and 2-aminopyrimidine In acetonitrile at 25℃; for 45h; Inert atmosphere; | 67% |
copper(I) bromide In acetonitrile at 45℃; for 72h; Oxidation; | 54% |
3,5-diphenyl-1,2,4-oxadiazole-4-oxide
cyclopentene
Conditions | Yield |
---|---|
In methanol Irradiation; | 99% |
In methanol at 20℃; for 5h; Irradiation; | 94% |
Conditions | Yield |
---|---|
With copper(l) iodide; C39H52Cl2N2O3Ru In diethyl ether at 35℃; for 16h; Cross Metathesis; Inert atmosphere; | 99% |
Hoveyda-Grubbs catalyst second generation In dichloromethane at 45℃; for 6h; | 86% |
Conditions | Yield |
---|---|
With diethylzinc In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere; | 99% |
With sodium dithionite; sodium hydrogencarbonate In acetonitrile at 20℃; for 6h; | 75% |
(1R,2S,7R,8S)-1,11,11-Trimethyl-6-oxy-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one
cyclopentene
C17H25NO3
Conditions | Yield |
---|---|
In toluene at 30℃; for 46h; | 99% |
(1S,2R,7S,8R)-8,11,11-Trimethyl-6-oxy-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one
cyclopentene
Conditions | Yield |
---|---|
In toluene at 30℃; for 25h; | 99% |
carbon monoxide
phenylhydrazine
cyclopentene
N-cyclopentylmethylene-N'-phenylhydrazine
Conditions | Yield |
---|---|
With hydrogen; toluene-4-sulfonic acid; acetylacetonatodicarbonylrhodium(l) In tetrahydrofuran at 100℃; under 52504.2 Torr; for 72h; | 99% |
Product Name: Cyclopentene (CAS NO.142-29-0)
Molecular Formula: C5H8
Molecular Weight: 68.117
Index of Refraction: 1.464
Molar Refractivity: 22.66 cm3
Molar Volume: 82 cm3
Surface Tension: 29.7 dyne/cm
Density: 0.83 g/cm3
Enthalpy of Vaporization: 27.63 kJ/mol
Boiling Point: 44.2 °C at 760 mmHg
Vapour Pressure: 378 mmHg at 25°C
Appearance: colorless liquid with a petrol-like odor
XLogP3-AA: 1.9
H-Bond Donor: 0
H-Bond Acceptor: 0
Structure Descriptors of Cyclopentene (CAS NO.142-29-0):
IUPAC Name: cyclopentene
Canonical SMILES: C1CC=CC1
InChI: InChI=1S/C5H8/c1-2-4-5-3-1/h1-2H,3-5H2
InChIKey: LPIQUOYDBNQMRZ-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates; Alkenes; Cyclic; Organic Building Blocks
Cyclopentene (CAS NO.142-29-0) is used as a monomer for synthesis of plastics, and in a number of chemical syntheses.
It can be obtained from vinylcyclopropane in the vinylcyclopropane-cyclopentene rearrangement.
1. | orl-rat LD50:1656 mg/kg | AIHAAP American Industrial Hygiene Association Journal. 30 (1969),470. | ||
2. | skn-rbt LD50:1231 mg/kg | AIHAAP American Industrial Hygiene Association Journal. 30 (1969),470. |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion and skin contact. A very dangerous fire hazard when exposed to flame or heat; can react with oxidizing materials. Keep away from heat and open flame. To fight fire, use foam, CO2, dry chemical.
Hazard Codes: F,Xn
Risk Statements: 11-21/22-36/37/38-65-67-52/53
R11:Highly flammable.
R21/22:Harmful in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R65:Harmful: may cause lung damage if swallowed.
R67:Vapours may cause drowsiness and dizziness.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 9-16-26-33-36-62-61-36/37
S9:Keep container in a well-ventilated place.
S16:Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S33:Take precautionary measures against static discharges.
S36:Wear suitable protective clothing.
S62:If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S36/37:Wear suitable protective clothing and gloves.
RIDADR: UN 2246 3/PG 2
WGK Germany: 3
RTECS: GY5950000
F: 10-23
HazardClass: 3
PackingGroup: II
DOT Classification: 3; Label: Flammable Liquid
The Cas Register Number of Cyclopentene is 142-29-0 .The chemical synonyms of Cyclopentene (CAS NO.142-29-0) are 3-cyclopentene cyclopentene ; Cyclopentene ; 1-Cyclopentene ; Cyclopent-1-ene .
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