627-19-0

Basic information

• Product Name: 1-PENTYNE
• Synonyms: Acetylene, propyl-;C3H7CequivCH;pent-1-yne;n-Propyl acetylene;PROPYLACETYLENE;1-PENTYNE;1-PENTYNE 98+%;1-Pentyne (6CI, 8CI, 9CI)
• CAS NO: 627-19-0
• Molecular Formula: C₅H₈
• Molecular Weight: 68.12
• EINECS: 210-987-1
• Product Categories: Miscellaneous;Acetylenes;Acetylenic Hydrocarbons;Alkynes;Organic Building Blocks;Terminal
• Mol File: 627-19-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: -106 °C
• Boiling Point: 40 °C(lit.)
• Flash Point: -34°C
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.691 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.8 psi ( 20 °C)
• Refractive Index: n20/D 1.385(lit.)
• Storage Temp.: 2-8°C
• Solubility: 1.05g/l
• Water Solubility: Soluble in water. (1.05 g/L) at 20°C.
• BRN: 1697133
• CAS DataBase Reference: 1-PENTYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PENTYNE(627-19-0)
• EPA Substance Registry System: 1-PENTYNE(627-19-0)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-36/37/38-65
• Safety Statements: 16-26-36-62
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 627-19-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to pale yellow liquid

Uses

Different sources of media describe the Uses of 627-19-0 differently. You can refer to the following data:
1. 1-Pentyne has been used in preparation of:lithium acetylides, required for asymmetric synthesis of α,α-dibranched propargyl sulfinamides. It is also used to synthesize 7-hydroxy-10-methoxy-3H-naphtho[2.1-b]pyrans.
2. 1-Pentyne has been used in preparation of:lithium acetylides, required for asymmetric synthesis of α,α-dibranched propargyl sulfinamides7-hydroxy-10-methoxy-3H-naphtho[2.1-b]pyrans

General Description

Selective and non-selective hydrogenation of 1-pentyne catalyzed by silica-supported palladium has been studied by in situ X-ray absorption spectroscopy.

Safety Profile

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

InChI:InChI=1/C5H8/c1-3-5-4-2/h1H,4-5H2,2H3

Synthetic route

1,2-dibromopentane (3234-49-9) → 1-Pentyne (627-19-0)

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 (17615-01-9) → 1-Pentyne (627-19-0)

Conditions	Yield
at 750℃; under 0.01 Torr;	59%
at 750℃;	59%

1-pentynyl lithium (18643-50-0) → 1-Pentyne (627-19-0) + deca-4,6-diyne (16387-71-6)

Conditions	Yield
With dinitrogen tetraoxide In diethyl ether at -78℃; for 0.166667h; Product distribution;	A 57% B 30%

sodium acetylide (1066-26-8) + propyl bromide (106-94-5) → 1-Pentyne (627-19-0)

Conditions	Yield
In ammonium hydroxide at -35℃;	56%
With ammonia
With tetrahydrofuran; N,N-dimethyl-formamide
In ammonia at -60℃;
In ammonia Alkylation;

pentanal (110-62-3) → 1-Pentyne (627-19-0)

Conditions	Yield
With Nonafluorobutanesulfonyl fluoride; tert-butylimino-tri(pyrrolidino)phosphorane In N,N-dimethyl-formamide at -10 - 20℃;	53%

hex-2-ynal (27593-24-4) → 1-Pentyne (627-19-0)

Conditions	Yield
With sodium hydroxide In methanol at 85℃;	40%

2-Pentyne (627-21-4) → 1-Pentyne (627-19-0)

Conditions	Yield
With sodium at 100℃; Zers. des gebildeten Natriumpropylacetylens durch Wasser;

penta-2,3-diene (591-96-8) → 1-Pentyne (627-19-0)

Conditions	Yield
With sodium at 100℃; Zers. des gebildeten Natriumpropylacetylens durch Wasser;

2-chloro-pent-2-ene (67747-70-0) → 1-Pentyne (627-19-0)

3-chloro-2-pentene (34238-52-3) → 1-Pentyne (627-19-0)

2-chloro-pent-1-ene (42131-85-1) → 1-Pentyne (627-19-0)

2-bromopent-1-ene (31844-95-8) → 1-Pentyne (627-19-0)

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 (26391-15-1) → 1-Pentyne (627-19-0)

Conditions	Yield
With ethanol; zinc at 78℃;

di-1-propyl sulfate (598-05-0) + sodium acetylide (1066-26-8) → 1-Pentyne (627-19-0)

Conditions	Yield
With ammonia

3-methyl-but-1-yne (598-23-2) → 2-Pentyne (627-21-4) + 1-Pentyne (627-19-0)

Conditions	Yield
Isomerisierung;

penta-1,2-diene (591-95-7) → 1-Pentyne (627-19-0)

Conditions	Yield
With petroleum; sodium amide at 140℃;

2,2-dichloro-pentane (34887-14-4) → 1-Pentyne (627-19-0)

2,3-dichloropentane (600-11-3) → 1-Pentyne (627-19-0)

sodium acetylide (1066-26-8) + 1-iodo-propane (107-08-4) → 1-Pentyne (627-19-0)

Conditions	Yield
With ammonia under 760 Torr;

2-Pentanone (107-87-9) → 1-Pentyne (627-19-0)

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

cyclopentene (142-29-0) → 1-methylbuta-1,3-diene (2004-70-8) + 1-Pentyne (627-19-0)

Conditions	Yield
at 1227℃; Equilibrium constant;

3-buten-1-yne (689-97-4) + (Z)-azomethane (4143-42-4) → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + 1-Pentyne (627-19-0) + 3-methyl-1-pentyne (922-59-8) + (Z)-3-methyl-1,3-pentadiene (2787-45-3)

Conditions	Yield
In gas at 299.9℃; Thermodynamic data; Rate constant; Kinetics; Heating; other temperature;

propene (187737-37-7) → 1-Pentyne (627-19-0) + 3-methyl-but-1-yne (598-23-2) + 6-Methyl-hept-1-en-4-yne (10288-14-9) + 1,1'-Dimethylethenebisallene (4356-63-2) + 1-octene-4-yne (24612-83-7) + 4-Methylhept-1-en-6-yne (120608-97-1)

Conditions	Yield
With Diatomic carbon at -196.1℃; Mechanism;

(E)/(Z)-1-bromo-1-pentene (60468-23-7) → 1-Pentyne (627-19-0) + cyclopentene (142-29-0)

Conditions	Yield
With potassium tert-butylate at 240℃; for 0.0166667h; Product distribution; Mechanism;

1-penten (109-67-1) → 1-Pentyne (627-19-0) + 2-Pentanone (107-87-9)

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 (1605-39-6) → 1-Pentyne (627-19-0) + ethyl 2-hexynoate (16205-90-6) + (Z)-ethyl 4-oxo-3-propyl-2-hepten-1-oate (73368-67-9) + (E)-ethyl 4-oxo-3-propyl-2-hepten-1-oate (73368-65-7) + butyric acid (107-92-6)

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 (10306-92-0) → 1-Pentyne (627-19-0) + trans-1,3-octadien-5-one (30647-86-0) + 5-nonyn-4-one (73368-69-1) + 2-propyl-1-hexen-3-one (73368-66-8)

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 (10306-92-0) → 1-Pentyne (627-19-0) + trans-1,3-octadien-5-one (30647-86-0) + 5-nonyn-4-one (73368-69-1) + 2-propyl-1-hexen-3-one (73368-66-8) + butyric acid (107-92-6)

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 (136449-60-0) → 1-Pentyne (627-19-0)

Conditions	Yield
With potassium carbonate In methanol	72 % Chromat.

C5H7(3)H (100312-91-2) → 1-Pentyne (627-19-0)

Conditions	Yield
With amine buffer; water at 25℃; Rate constant; μ = 0.10 M;

1-Pentyne (627-19-0) + hexakis[2-(dimethylaminomethyl)phenyl]cyclotrisilane (143504-44-3) → Dimethyl-{2-[1,2,2-tris-(2-dimethylaminomethyl-phenyl)-4-propyl-1,2-dihydro-[1,2]disilet-1-yl]-benzyl}-amine (158817-37-9)

Conditions	Yield
In benzene-d6 at 55℃; for 10h;	100%

1-Pentyne (627-19-0) + benzaldehyde (100-52-7) → 1-Phenyl-2-hexin-1-ol (108946-34-5)

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;

1-Pentyne (627-19-0) + 2-iodophenylamine (615-43-0) → 2-(pent-1-yn-1-yl)aniline (26059-38-1)

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%

2-bromo-pyridine (109-04-6) + 1-Pentyne (627-19-0) → 2-(pent-1'-ynyl)-pyridine (202828-84-0)

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 (627-19-0) + acetic acid 1-acetoxymethyl-2-(4-bromo-2-nitro-phenyl)-ethyl ester (442521-49-5) → acetic acid 1-acetoxymethyl-2-(2-nitro-4-pent-1-ynyl-phenyl)-ethyl ester (442521-50-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 18h; Sonogashira coupling;	100%

1-Pentyne (627-19-0) + 1-Bromo-2-iodobenzene (583-55-1) → 1-bromo-2-(n-propylethynyl)benzene (194092-09-6)

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 (443864-69-5) + 1-Pentyne (627-19-0) → methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-propyl-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside

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 (494194-61-5) + 1-Pentyne (627-19-0) → 5-methyl-2,4-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%

2,4-dibromo-5,6-dimethyl-pyrimidine (753470-32-5) + 1-Pentyne (627-19-0) → 4,5-dimethyl-2,6-di-pent-1-ynyl-pyrimidine (753470-52-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling;	100%

1-Pentyne (627-19-0) + 2-(dimethylamino)benzaldehyde (579-72-6) → 1-(2-dimethylaminophenyl)hex-2-yn-1-ol (876460-06-9)

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 (627-19-0) + ethyl chlorocarbonylacetate (36239-09-5) → 3-oxo-oct-4-ynoic acid ethyl ester (861144-51-6)

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%

1-Pentyne (627-19-0) + (R)-propylene oxide (15448-47-2) → (R)-oct-4-yn-2-ol (907157-39-5)

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 (909275-31-6) + 1-Pentyne (627-19-0) → 2-(pent-1-ynyl)phenyl methoxymethyl sulfide (909275-32-7)

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride at 20℃; Sonogashira coupling;	100%

1-Pentyne (627-19-0) + cyclohexane-1,2-epoxide (286-20-4) → trans-2-(1-pentynyl)cyclohexan-1-ol

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 (627-19-0) + trifluoro-methanesulfonic acid 3-methoxy-2-methyl-6-nitro-phenyl ester (835883-30-2) → C13H15NO3 (1148008-83-6)

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 (627-19-0) + N,N-diethyl-2-iodo-3-methoxy-4-(methoxymethoxy)benzamide (1161720-15-5) → N,N-diethyl-3-methoxy-4-(methoxymethoxy)-2-(pent-1-yn-1-yl)benzamide (1161720-16-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethylamine at 60℃; for 35h; Sonogashira coupling; Inert atmosphere;	100%

1-Pentyne (627-19-0) + o-iodo-methyl-benzoic acid (610-97-9) → methyl 2-(pent-1-yn-1-yl)benzoate (90584-93-3)

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 (627-19-0) → deca-4,6-diyne (16387-71-6)

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%

1-Pentyne (627-19-0) + 2-iodochlorobenzene (615-41-8) → 1-(2-chlorophenyl)-1-pentyne (600174-97-8)

Conditions	Yield
With copper(l) iodide; diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 84℃; for 6h; Sonogashira coupling;	99%

1-Pentyne (627-19-0) + benzyl 2-formyl-4-isopropoxy-5-methoxyphenyl sulfide (445483-23-8) → benzyl 2-(1-hydroxy-2-hexynyl)-4-isopropoxy-5-methoxyphenyl sulfide (618388-71-9)

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%

1-Pentyne (627-19-0) + benzyl azide (622-79-7) → 1‐benzyl‐4‐propyl‐1H‐1,2,3‐triazole

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%

C10H11F3N2O4S (1006880-54-1) + 1-Pentyne (627-19-0) → N-(3-pent-1-ynyl-pyridin-2-yl)butyramide (1006880-56-3)

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 (60-29-7) + 1-Pentyne (627-19-0) + 1,4-bromoiodobenzene (589-87-7) + palladium diacetate (3375-31-3) → 1-bromo-4-(pent-1-yn-1-yl)benzene (109027-84-1)

Conditions	Yield
With triphenylphosphine In hexane; triethylamine	99%

1-Pentyne (627-19-0) + 3,5-dichloro-1-(4-methoxybenzyl)pyrazin-2(1H)-one (393860-82-7) → C17H17ClN2O2 (1011736-21-2)

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%

1-Pentyne (627-19-0) + trimethyltin(IV)chloride (1066-45-1) → trimethyl pentynyl stannane (1118-50-9)

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 (627-19-0) + 2-Iodobenzoic acid,benzyl ester (67460-10-0) → o-pent-1-ynylbenzoic acid benzyl ester

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira coupling; Inert atmosphere;	99%

1-Pentyne (627-19-0) + 6-hydroxymethyl-5-iodo-1-isopropyl-1H-indazole (1202528-38-8) → 6-hydroxymethyl-1-isopropyl-5-(1-pentynyl)-1H-indazole (1202528-40-2)

Conditions	Yield
copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride In N,N-dimethyl-formamide at 20℃; for 12h;	99%

1-Pentyne (627-19-0) + [(1S,2S)-1-({(4-bromophenyl)[trans-2-(6-fluoropyridin-2-yl)cyclopropanecarbonyl]amino}methyl)-2-methylbutyl]carbamic acid tert-butyl ester (1287206-05-6) → ((1S,2S)-1-{[[(1S,2S)-2-(6-fluoropyridin-2-yl)cyclopropanecarbonyl]-(4-pent-1-ynylphenyl)amino]methyl}-2-methylbutyl)carbamic acid t-butyl ester

Conditions	Yield
With tetrabutyl ammonium fluoride; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 90℃; for 0.5h; Microwave irradiation;	99%

3-phenyl-propionaldehyde (104-53-0) + 1-Pentyne (627-19-0) → 1-phenyl-4-octyn-3-ol (107383-34-6)

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 (627-19-0) + C11H10INO2 (1387004-47-8) → ethyl 5-(pent-1-yn-1-yl)-1H-indole-1-carboxylate (1439383-33-1)

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%

Upstream product

• 42131-85-1 2-chloro-pent-1-ene 
• 31844-95-8 2-bromopent-1-ene 
• 598-23-2 3-methyl-but-1-yne 
• 187737-37-7 propene 
• 60468-23-7 (E)/(Z)-1-bromo-1-pentene 
• 27593-24-4 hex-2-ynal 
• 820-55-3 1,1-dichloropentane 
• 110-62-3 pentanal 
• 764-33-0 hex-2-ynoic acid 
• 56-23-5 tetrachloromethane 
• 627-21-4 2-Pentyne 
• 100312-91-2 C₅H₇⁽³⁾H 
• 136449-60-0 Biphenyl-4-yl-dimethyl-pent-1-ynyl-silane 
• 17615-01-9 1-(triphenyl-λ⁵-phosphanylidene)pentan-2-one 

Downstream Products

• 40962-11-6 4,5-Di-n-propyl-1,1,2,2-tetracyan-3-triethoxysilyl-cyclohex-4-en 
• 143901-63-7 5,6-dimethyl-2-(1-pentenyl)pyrazine 
• 18388-22-2 3-(trimethylsilyl)-1-pentene 
• 764-35-2 2-Hexyne 
• 34491-84-4 2-n-propyl-1,4-naphthoquinone 
• 51110-41-9 3-(pentadeca-8,11-diynyl)phenol 
• 51110-45-3 3-(pentadeca-8,11-diynyl)anisole 
• 36384-80-2 3-Hydroxy-6-oxo-1,5-di-tert-butyl-3-pentinyl-cyclohexa-1,4-dien 
• 174229-55-1 2-[1-Isobutoxy-meth-(E)-ylidene]-1-pent-1-ynyl-cyclohexanol 
• 173473-59-1 2-Methoxy-6-(8,11-pentadecadiynyl)benzoic acid 
• 16387-71-6 deca-4,6-diyne 
• 157142-25-1 6,7-Bis(methylene)-4,8-dodecadiyne 
• 175883-83-7 4,5-di(1-pentynyl)phthalonitrile 
• 26059-38-1 2-(pent-1-yn-1-yl)aniline 

Relevant articles and documents

Unexpected conformational behavior of gaseous 1-pentyne

The molecular structure and conformations of 1-pentyne have been studied experimentally by the gas electron diffraction method. A conformational mixture of 68.6% gauche and 31.4% anti, with standard deviation equal to 4.5%, was observed. Results from ab initio MP2/6-31G* optimization calculations are in excellent agreement with those observed.

TiO2 Assisted Photocatalytic Decomposition of 2-Chloronaphthalene on Iron Nanoparticles in Aqueous Systems: Synergistic Effect and Intermediate Products

Abstract: 2-Chloronaphthalene (2-CN), used as an intermediate for organic synthesis, is a new type of persistent organic pollutant. In this work, the decomposition efficiency and decomposition mechanism of 2-CN by zero-valent iron (ZVI) assisted TiO2

An Additive-Free, Base-Catalyzed Protodesilylation of Organosilanes

We report an additive-free, base-catalyzed C-, N-, O-, and S-Si bond cleavage of various organosilanes in mild conditions. The novel catalyst system exhibits high efficiency and good functional group compatibility, providing the corresponding products in good to excellent yields with low catalyst loadings. Overall, this transition-metal-free process may offer a convenient and general alternative to current employing excess bases, strong acids, or metal-catalyzed systems for the protodesilylation of organosilanes.