Conditions | Yield |
---|---|
With potassium hydroxide In xylene Heating; | 94% |
With Aliquat 336; potassium hydroxide In water at 120℃; for 7h; | 80.9% |
With petroleum; sodium amide at 160 - 170℃; | |
With potassium hydroxide; mineral oil at 250℃; |
1-(triphenyl-λ5-phosphanylidene)pentan-2-one
1-Pentyne
Conditions | Yield |
---|---|
at 750℃; under 0.01 Torr; | 59% |
at 750℃; | 59% |
Conditions | Yield |
---|---|
With dinitrogen tetraoxide In diethyl ether at -78℃; for 0.166667h; Product distribution; | A 57% B 30% |
Conditions | Yield |
---|---|
In ammonium hydroxide at -35℃; | 56% |
With ammonia | |
With tetrahydrofuran; N,N-dimethyl-formamide | |
In ammonia at -60℃; | |
In ammonia Alkylation; |
Conditions | Yield |
---|---|
With Nonafluorobutanesulfonyl fluoride; tert-butylimino-tri(pyrrolidino)phosphorane In N,N-dimethyl-formamide at -10 - 20℃; | 53% |
hex-2-ynal
1-Pentyne
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 85℃; | 40% |
Conditions | Yield |
---|---|
With sodium at 100℃; Zers. des gebildeten Natriumpropylacetylens durch Wasser; |
Conditions | Yield |
---|---|
With sodium at 100℃; Zers. des gebildeten Natriumpropylacetylens durch Wasser; |
2-chloro-pent-2-ene
1-Pentyne
3-chloro-2-pentene
1-Pentyne
2-chloro-pent-1-ene
1-Pentyne
2-bromopent-1-ene
1-Pentyne
Conditions | Yield |
---|---|
With sodium amide; xylene at 150℃; Zersetzung des Reaktionsprodukts mit Wasser; | |
Multi-step reaction with 3 steps 1: chloroform; bromine 2: sodium ethylate 3: zinc; alcohol / 78 °C View Scheme |
1,2-dibromo-pent-1-ene
1-Pentyne
Conditions | Yield |
---|---|
With ethanol; zinc at 78℃; |
Conditions | Yield |
---|---|
With ammonia |
Conditions | Yield |
---|---|
Isomerisierung; |
Conditions | Yield |
---|---|
With petroleum; sodium amide at 140℃; |
2,2-dichloro-pentane
1-Pentyne
Conditions | Yield |
---|---|
With ammonia under 760 Torr; |
Conditions | Yield |
---|---|
With phosphorus pentachloride; potassium carbonate at 120℃; | |
Multi-step reaction with 2 steps 1: phosphorus pentachloride View Scheme | |
Multi-step reaction with 2 steps 1: phosphorus pentachloride View Scheme |
Conditions | Yield |
---|---|
at 1227℃; Equilibrium constant; |
3-buten-1-yne
(Z)-azomethane
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
1-Pentyne
D
3-methyl-1-pentyne
E
(Z)-3-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
In gas at 299.9℃; Thermodynamic data; Rate constant; Kinetics; Heating; other temperature; |
propene
A
1-Pentyne
B
3-methyl-but-1-yne
C
6-Methyl-hept-1-en-4-yne
D
1,1'-Dimethylethenebisallene
E
1-octene-4-yne
F
4-Methylhept-1-en-6-yne
Conditions | Yield |
---|---|
With Diatomic carbon at -196.1℃; Mechanism; |
Conditions | Yield |
---|---|
With potassium tert-butylate at 240℃; for 0.0166667h; Product distribution; Mechanism; |
Conditions | Yield |
---|---|
With perchloric acid; air; Pd(OAc)2-OPTA In ethanol at 25℃; for 3.5h; | A 89 % Chromat. B 11 % Chromat. |
With perchloric acid; air In ethanol at 25℃; for 3.5h; Product distribution; various reaction conditions; also for other n-alkenes; | A 89 % Chromat. B 11 % Chromat. |
ethyl 1,2-dipropyl-1-cyclopropene-3-carboxylate
A
1-Pentyne
B
ethyl 2-hexynoate
C
(Z)-ethyl 4-oxo-3-propyl-2-hepten-1-oate
D
(E)-ethyl 4-oxo-3-propyl-2-hepten-1-oate
E
butyric acid
Conditions | Yield |
---|---|
With oxygen In acetonitrile Product distribution; Mechanism; Irradiation; other solvents (sensitizers: methylene blue, MB; rose bengal, RB; polymer-based rose bengal, p-RB); |
1,2-di-n-propylcyclopropene
A
1-Pentyne
B
trans-1,3-octadien-5-one
C
5-nonyn-4-one
D
2-propyl-1-hexen-3-one
Conditions | Yield |
---|---|
With oxygen In acetonitrile Irradiation; other solvents (sensitizer: methylene blue, MB; rose bengal, RB); Yield given. Further byproducts given; | |
With oxygen In acetonitrile Irradiation; other solvents (sensitizer: methylene blue, MB; rose bengal, RB); Further byproducts given; |
1,2-di-n-propylcyclopropene
A
1-Pentyne
B
trans-1,3-octadien-5-one
C
5-nonyn-4-one
D
2-propyl-1-hexen-3-one
E
butyric acid
Conditions | Yield |
---|---|
With oxygen In acetonitrile Product distribution; Mechanism; Irradiation; other solvents (sensitizers: methylene blue, MB; rose bengal, RB; polymer based rose bengal, p-RB); |
Biphenyl-4-yl-dimethyl-pent-1-ynyl-silane
1-Pentyne
Conditions | Yield |
---|---|
With potassium carbonate In methanol | 72 % Chromat. |
C5H7(3)H
1-Pentyne
Conditions | Yield |
---|---|
With amine buffer; water at 25℃; Rate constant; μ = 0.10 M; |
1-Pentyne
hexakis[2-(dimethylaminomethyl)phenyl]cyclotrisilane
Dimethyl-{2-[1,2,2-tris-(2-dimethylaminomethyl-phenyl)-4-propyl-1,2-dihydro-[1,2]disilet-1-yl]-benzyl}-amine
Conditions | Yield |
---|---|
In benzene-d6 at 55℃; for 10h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1-Pentyne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1.5h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; | 100% |
Stage #1: 1-Pentyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran; hexane at 20℃; for 2h; | 98% |
Yield given. Multistep reaction; | |
Stage #1: 1-Pentyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 0℃; for 6h; |
Conditions | Yield |
---|---|
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | 100% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | 94% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide for 48h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In triethylamine at 25℃; for 16h; Sonogashira coupling; | 100% |
Stage #1: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 25℃; for 0.5h; Inert atmosphere; Stage #2: 1-Pentyne at 25℃; for 16h; Inert atmosphere; | 94% |
Stage #1: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 25℃; for 0.5h; Inert atmosphere; Stage #2: 1-Pentyne at 25℃; for 16h; Inert atmosphere; | 94% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethylamine for 20h; Ambient temperature; | 84% |
Stage #1: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine for 0.5h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: 1-Pentyne for 18h; Sonogashira Cross-Coupling; Inert atmosphere; Darkness; | 78% |
1-Pentyne
acetic acid 1-acetoxymethyl-2-(4-bromo-2-nitro-phenyl)-ethyl ester
acetic acid 1-acetoxymethyl-2-(2-nitro-4-pent-1-ynyl-phenyl)-ethyl ester
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 18h; Sonogashira coupling; | 100% |
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 20℃; for 8h; Inert atmosphere; | 100% |
Stage #1: 1-Bromo-2-iodobenzene With bis-triphenylphosphine-palladium(II) chloride; triethylamine for 0.166667h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: 1-Pentyne With copper(l) iodide at 20℃; Sonogashira Cross-Coupling; Inert atmosphere; | 100% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 4h; Sonogashira coupling; | 96% |
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-4-azido-6-(methylthio)tetrahydro-2H-pyran-3,5-diyl diacetate
1-Pentyne
Conditions | Yield |
---|---|
With copper; N-ethyl-N,N-diisopropylamine In toluene at 45℃; | 100% |
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In toluene at 50℃; for 72h; | 100% |
With copper(l) iodide; N-ethyl-N,N-diisopropylamine In toluene at 50℃; for 72h; regioselective reaction; | 99% |
2,4-dibromo-5-methyl-pyrimidine
1-Pentyne
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling; | 100% |
2,4-dibromo-5,6-dimethyl-pyrimidine
1-Pentyne
4,5-dimethyl-2,6-di-pent-1-ynyl-pyrimidine
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling; | 100% |
1-Pentyne
2-(dimethylamino)benzaldehyde
1-(2-dimethylaminophenyl)hex-2-yn-1-ol
Conditions | Yield |
---|---|
Stage #1: 1-Pentyne With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Stage #2: 2-(dimethylamino)benzaldehyde In tetrahydrofuran; hexane for 0.15h; | 100% |
1-Pentyne
ethyl chlorocarbonylacetate
3-oxo-oct-4-ynoic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 1-Pentyne With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 6h; Stage #2: ethyl chlorocarbonylacetate In tetrahydrofuran at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1-Pentyne With n-butyllithium In tetrahydrofuran; hexane at -40 - 0℃; for 0.5h; Stage #2: (R)-propylene oxide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -20 - 20℃; for 16.5h; | 100% |
2-iodophenyl methoxymethyl sulfide
1-Pentyne
2-(pent-1-ynyl)phenyl methoxymethyl sulfide
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride at 20℃; Sonogashira coupling; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1-Pentyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: cyclohexane-1,2-epoxide With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 3h; | 100% |
Stage #1: 1-Pentyne With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: cyclohexane-1,2-epoxide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water | 68% |
1-Pentyne
trifluoro-methanesulfonic acid 3-methoxy-2-methyl-6-nitro-phenyl ester
C13H15NO3
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetra-(n-butyl)ammonium iodide In triethylamine; acetonitrile Sonogashira-Hagihara coupling; Reflux; | 100% |
1-Pentyne
N,N-diethyl-2-iodo-3-methoxy-4-(methoxymethoxy)benzamide
N,N-diethyl-3-methoxy-4-(methoxymethoxy)-2-(pent-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethylamine at 60℃; for 35h; Sonogashira coupling; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 24h; Arylation; | 99% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; Condensation; | 99% |
With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 24h; Sonogashira coupling reaction; | 98% |
1-Pentyne
deca-4,6-diyne
Conditions | Yield |
---|---|
With oxygen; palladium on activated charcoal; copper(l) iodide In dimethyl sulfoxide at 20℃; for 24h; | 99% |
With N,N,N,N,-tetramethylethylenediamine In dichloromethane at 130℃; under 37503.8 Torr; for 0.333333h; Flow reactor; chemoselective reaction; | 98% |
With copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 25℃; for 24h; | 96% |
Conditions | Yield |
---|---|
With copper(l) iodide; diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 84℃; for 6h; Sonogashira coupling; | 99% |
1-Pentyne
benzyl 2-formyl-4-isopropoxy-5-methoxyphenyl sulfide
benzyl 2-(1-hydroxy-2-hexynyl)-4-isopropoxy-5-methoxyphenyl sulfide
Conditions | Yield |
---|---|
Stage #1: 1-Pentyne With n-butyllithium In tetrahydrofuran at -78℃; for 0.15h; Stage #2: benzyl 2-formyl-4-isopropoxy-5-methoxyphenyl sulfide In tetrahydrofuran at 18℃; for 0.25h; | 99% |
Conditions | Yield |
---|---|
With triethylamine In neat (no solvent) at 70℃; for 8h; Huisgen Cycloaddition; regioselective reaction; | 99% |
With [copper(I)]2[(2-picolyliminomethyl)pyrrole]2 In dichloromethane at 20℃; for 4h; Inert atmosphere; | 99% |
With Cu(I)complex of dendrimer of triazole rings with triethylene glycol termini In water at 30℃; for 24h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 20℃; Sonogashira coupling; | 99% |
diethyl ether
1-Pentyne
1,4-bromoiodobenzene
palladium diacetate
1-bromo-4-(pent-1-yn-1-yl)benzene
Conditions | Yield |
---|---|
With triphenylphosphine In hexane; triethylamine | 99% |
1-Pentyne
3,5-dichloro-1-(4-methoxybenzyl)pyrazin-2(1H)-one
C17H17ClN2O2
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 80℃; for 0.166667h; Sonogashira coupling; microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With methyllithium In diethyl ether dropwise addn. of CH3Li to a soln. of 1-pentyne (-20°C, inert atmosphere), stirring 1 h, warming to 0°C, addn. of (CH3)3SnCl (ether), warming to room temp. while stirring (12 h); removal of solvent, fractional distillation, distillation; | 99% |
1-Pentyne
2-Iodobenzoic acid,benzyl ester
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira coupling; Inert atmosphere; | 99% |
1-Pentyne
6-hydroxymethyl-5-iodo-1-isopropyl-1H-indazole
6-hydroxymethyl-1-isopropyl-5-(1-pentynyl)-1H-indazole
Conditions | Yield |
---|---|
copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride In N,N-dimethyl-formamide at 20℃; for 12h; | 99% |
1-Pentyne
[(1S,2S)-1-({(4-bromophenyl)[trans-2-(6-fluoropyridin-2-yl)cyclopropanecarbonyl]amino}methyl)-2-methylbutyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 90℃; for 0.5h; Microwave irradiation; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-Pentyne With n-butyllithium In tetrahydrofuran; hexane at -78 - -15℃; Inert atmosphere; Stage #2: 3-phenyl-propionaldehyde In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 99% |
1-Pentyne
C11H10INO2
ethyl 5-(pent-1-yn-1-yl)-1H-indole-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: 1-Pentyne; C11H10INO2 With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With copper(l) iodide In tetrahydrofuran at 20℃; Inert atmosphere; | 99% |
IUPAC Name: 1-Pentyne
The MF of 1-Pentyne (627-19-0) is C5H8.
The MW of 1-Pentyne (627-19-0) is 68.12.
Synonyms of 1-Pentyne (627-19-0): Acetylene, propyl- ; Ethylmethylacetylene ; Pent-1-in
Product Categories: Miscellaneous;Acetylenes;Alkynes;Organic Building Blocks;Terminal
Form: Clear colorless to pale yellow liquid
Index of Refraction: 1.401
Density: 0.718 g/ml
Flash Point: -34 °C
Boiling Point: 40.9 °C
Melting Point: -106 °C
Storage temp: 2-8 °C
BRN: 1697133
1-Pentyne (627-19-0) is used as organic synthesis.
Dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes. See also ACETYLENE COMPOUNDS and ALKYNES.
Safety information of 1-Pentyne (627-19-0):
Hazard Codes F,Xn
Risk Statements
11 Highly Flammable
36/37/38 Irritating to eyes, respiratory system and skin
65 Harmful: May cause lung damage if swallowed
Safety Statements
16 Keep away from sources of ignition - No smoking
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36 Wear suitable protective clothing
62 If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label
RIDADR UN 3295 3/PG 2
WGK Germany 3
HazardClass 3
PackingGroup II
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