74-99-7

Basic information

• Product Name: 1-Propyne
• Synonyms: Propyne(8CI);Allylene;Methylacetylene;1-Propyne
• CAS NO: 74-99-7
• Molecular Formula: C₃H₄
• Molecular Weight: 40.06386
• EINECS: 200-828-4
• Mol File: 74-99-7.mol
• Article Data: 153

Chemical Properties

• Melting Point: -102.7℃
• Boiling Point: -23.2 °C(lit.)
• Flash Point: -51 °C
• Appearance: /
• Density: 0.648 g/cm³
• Vapor Pressure: 4570mmHg at 25°C
• Refractive Index: 1.363
• CAS DataBase Reference: 1-Propyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propyne(74-99-7)
• EPA Substance Registry System: 1-Propyne(74-99-7)

Safety Data

• Hazard Codes: F:Flammable;;
• Statements: R11:; R37:
• Safety Statements: S16:; S36:; S38:
• Hazardous Substances Data: 74-99-7(Hazardous Substances Data)

Usage

General Description

1-Propyne, also known as methylacetylene, is a colorless, flammable gas with a faintly sweet odor. It is a simple alkyne compound with the chemical formula C3H4 and is used as a fuel gas for high-temperature cutting and welding. 1-Propyne is also used in the synthesis of organic chemicals and pharmaceuticals. It can react violently with oxidizing agents and is incompatible with strong bases and strong acids. Inhaling high levels of 1-Propyne can cause dizziness, headaches, and nausea, while skin contact can cause irritation and burns. Proper handling and storage procedures should be followed to minimize the risk of exposure to this chemical.

InChI:InChI=1/C3H4/c1-3-2/h1H,2H3

Synthetic route

4-Phenyl-1-butyne (16520-62-0) + benzyl(but-2-yn-1-yl)amine (4626-58-8) → N-benzyl-5-phenylpent-2-yn-1-amine + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 95% B n/a

acetaldehyde (75-07-0) + C8H21N4PSi (145397-30-4) → α-trimethylsilyloxyethyl-N,N,N',N'-tetramethylphosphondiamide + prop-1-yne (74-99-7)

Conditions	Yield
In pentane at 20℃;	A 91% B n/a

2-cyclohexylacetylene (931-48-6) + benzyl(but-2-yn-1-yl)amine (4626-58-8) → N-benzyl-3-cyclohexylprop-2-yn-1-amine + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 90% B n/a

benzyl(but-2-yn-1-yl)amine (4626-58-8) + 4-n-methylphenylacetylene (766-97-2) → N-benzyl-3-(4-methylphenyl)-2-propynylamine (1273578-50-9) + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 87% B n/a

4-methylpentyne (7154-75-8) + benzyl(but-2-yn-1-yl)amine (4626-58-8) → N-benzyl-5-methylhex-2-yn-1-amine + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 87% B n/a

benzyl(but-2-yn-1-yl)amine (4626-58-8) + hex-1-yne (693-02-7) → N-benzylhept-2-yn-1-amine (1379038-80-8) + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 120℃; for 12h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 87% B n/a

Cyclopropylacetylene (6746-94-7) + benzyl(but-2-yn-1-yl)amine (4626-58-8) → N-benzyl 3-cyclopropyl-prop-2-ynylamine + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 86% B n/a

benzyl(but-2-yn-1-yl)amine (4626-58-8) + phenylacetylene (536-74-3) → N-(3-phenylprop-2-ynyl)benzenemethanamine (40032-57-3) + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 85% B n/a

sodium acetylide (1066-26-8) + methyl iodide (74-88-4) → prop-1-yne (74-99-7)

Conditions	Yield
In ammonia	84%
With ammonia

1-ethynyl-4-fluorobenzene (766-98-3) + benzyl(but-2-yn-1-yl)amine (4626-58-8) → N-benzyl-3-(4-fluorophenyl)prop-2-yn-1-amine + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 80% B n/a

2,2-dimethyl-3-butyne (917-92-0) + benzyl(but-2-yn-1-yl)amine (4626-58-8) → N-benzyl 4,4-dimethyl-pent-2-ynylamine (1610010-33-7) + prop-1-yne (74-99-7)

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 80% B n/a

1-(4-methoxyphenyl)-4-(triphenylphosphoranylidene)hexane-1,5-dione → 1-(4-methoxyphenyl)prop-2-en-1-one (7448-86-4) + prop-1-yne (74-99-7)

Conditions	Yield
at 650℃; under 0.01 - 0.1 Torr; for 2h;	A 79% B n/a

triphenylprop-2-ynylarsonium bromide (5903-83-3) → 1,2-propanediene (463-49-0) + triphenylarsineoxide (1153-05-5, 856568-31-5) + prop-1-yne (74-99-7)

Conditions	Yield
With potassium hydroxide In methanol; water at 25℃; for 1h;	A n/a B 71.51% C n/a

tributyl(2-bromo-2-propenyl)phosphonium bromide → Tributylphosphine oxide (814-29-9) + prop-1-yne (74-99-7)

Conditions	Yield
With potassium hydroxide In water for 1h; Hydrolysis; Heating;	A 66% B 70%

protoanemonin (108-28-1) → 1,2-propanediene (463-49-0) + maleic anhydride (930-60-9) + prop-1-yne (74-99-7)

Conditions	Yield
at 1100℃;	A 10% B 60% C 25%

3-(triphenylphosphoranylidene)octane-2,6-dione (163495-05-4) → 4-penten-3-one (1629-58-9) + oct-6-yn-3-one (26118-44-5) + prop-1-yne (74-99-7)

Conditions	Yield
at 650℃; under 0.01 - 0.1 Torr; for 2h;	A 49% B 39% C n/a

dimethylglyoxal (431-03-8) → dimethylketene (598-26-5) + propene (187737-37-7) + carbon dioxide (124-38-9) + methyl vinyl ketone (78-94-4) + prop-1-yne (74-99-7) + acetylene (74-86-2)

Conditions	Yield
With pyrographite at -196℃; Mechanism;	A 2% B 22.4% C 9.4% D 19% E 2.3% F 40.7%

(p-fluorophenyl)dimethyl(1-propynyl)stannane (93247-03-1) + 4-ethynyl-N,N-dimethylaniline (17573-94-3) → {(p-(dimethylamino)phenyl)ethynyl}(p-fluorophenyl)dimethylstannane (93246-99-2) + prop-1-yne (74-99-7)

Conditions	Yield
In neat (no solvent) (vac.); mixing Sn-compd. with org. compd. in stream of Ar, heating (150°C), keeping (160-175°C, 10 h); distn. (vac.), collection (155°C and higher, 0.08 mm), recrystn. (hexane/CCl4); elem. anal.;	A 36% B n/a
In neat (no solvent) (vac.); mixing Sn-compd. with org. compd. in stream of Ar, heating (150°C), keeping (160-175°C, 5 h),; distn. (vac.), collection (155°C and higher, 0.08 mm), recrystn. (hexane/CCl4); elem. anal.;	A 33% B n/a

3-(triphenylphosphoranylidene)heptane-2,6-dione (193155-13-4) → 5-heptyne-2-one (22592-18-3) + methyl vinyl ketone (78-94-4) + prop-1-yne (74-99-7)

Conditions	Yield
at 750℃; under 0.01 - 0.1 Torr; for 2h;	A 33% B 28% C n/a
at 650℃; under 0.01 - 0.1 Torr; for 2h;	A 26% B 32% C n/a

1-Methyl-1-ethenylsilacyclobutane (3514-67-8) → propene (187737-37-7) + ethene (74-85-1) + 1,2-propanediene (463-49-0) + buta-1,3-diene (106-99-0) + prop-1-yne (74-99-7) + 1,3-dimethyl-1,3-divinyl-1,3-disilacyclobutane (22053-38-9)

Conditions	Yield
at 775℃; under 0.008 - 0.08 Torr; Product distribution; Mechanism; other temperature;	A 1.4% B 8% C 3.6% D n/a E 1.7% F 28%

1-Methyl-1-ethenylsilacyclobutane (3514-67-8) → ethene (74-85-1) + 1,2-propanediene (463-49-0) + prop-1-yne (74-99-7) + 1,3-dimethyl-1,3-divinyl-1,3-disilacyclobutane (22053-38-9)

Conditions	Yield
at 775℃; under 0.008 - 0.08 Torr; Further byproducts given;	A 8% B 3.6% C 1.7% D 28%
Kinetics; Thermodynamic data; low pressure pyrolysis; also co-pyrolysis with 1,1-dimethyl-1-silacyclobutane; var. temp.;

2,3-dimethyl-buta-1,3-diene (513-81-5) + 1,1-Divinyl-1-silacyclobutane (74045-42-4) → propene (187737-37-7) + ethene (74-85-1) + Allylmethylvinylsilan + 3,4-Dimethyl-1-sila-1-vinylcyclopent-3-en + prop-1-yne (74-99-7) + acetylene (74-86-2) + aromatic hydrocarbons, Si-compounds

Conditions	Yield
at 820℃; under 0.008 - 0.08 Torr; Product distribution; Mechanism;	A 3% B 21% C 8% D 14% E 4% F 18% G n/a

...Expand

furan (110-00-9) → ethene (74-85-1) + prop-1-yne (74-99-7) + acetylene (74-86-2)

Conditions	Yield
at 700℃; Pyrolysis;

pyridine (110-86-1) + 2-Butynoic acid (590-93-2) → 2,4-hexadiyne (2809-69-0) + prop-1-yne (74-99-7)

Conditions	Yield
Reaktion des Kupfersalzes;

methyl bromide (74-83-9) + sodium acetylide (1066-26-8) → prop-1-yne (74-99-7)

Conditions	Yield
With tetrahydrofuran; N,N-dimethyl-formamide

2-chloropropene (557-98-2) + potassium cyanide (151-50-8) → prop-1-yne (74-99-7)

2-chloropropene (557-98-2) + sodium ethanolate (141-52-6) → prop-1-yne (74-99-7)

2-chloropropene (557-98-2) → prop-1-yne (74-99-7)

Conditions	Yield
With potassium carbonate
With sodium ethanolate

2,3-Dichloroprop-1-ene (78-88-6) → propene (187737-37-7) + prop-1-yne (74-99-7)

Conditions	Yield
With sodium

trans-Crotonaldehyde (123-73-9) + prop-1-yne (74-99-7) → (E)-2-hepten-5-yn-4-ol (63124-69-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; pentane at -78℃; for 0.833333h;	100%
(i) EtMgBr, Et2O, (ii) /BRN= 1209254/; Multistep reaction;

2-iodobenzonitrile (4387-36-4) + prop-1-yne (74-99-7) → 2-(prop-1-yn-1-yl)benzonitrile (110166-79-5)

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride for 6h; Ambient temperature;	100%

N-methoxy-N-methyl-3,3-dimethylacrylamide (121712-53-6) + prop-1-yne (74-99-7) → 2-Methyl-2-hepten-5-yn-4-one (103576-51-8)

Conditions	Yield
With n-butyllithium; triphenylmethane 1.) -78 deg C, 15 min, 2.) r.t., 3 h;	100%

prop-1-yne (74-99-7) → 4-methyl-1,3,2-dithiazolium hexafluoroarsenate(V) (88047-50-1)

Conditions	Yield
With dichlorodithionitronium hexafluoroarsenate In liquid sulphur dioxide	100%
With dithionitronium hexafluoroarsenate In liquid sulphur dioxide Yield given;
With dithionitronium hexafluoroarsenate In liquid sulphur dioxide for 6h; Ambient temperature;

1-(Methoxymethoxy)-2-butanone (170450-99-4) + prop-1-yne (74-99-7) → 3-<(Methoxymethoxy)methyl>-4-hexyn-3-ol (170450-89-2)

Conditions	Yield
With ethylmagnesium bromide In tetrahydrofuran 1.) -78 deg C to r.t.; r.t., 1 h, 2.) 0 deg C to r.t., 1 h;	100%

2-iodophenylamine (615-43-0) + prop-1-yne (74-99-7) → 1-(2-aminophenyl)prop-1-yne (220465-91-8)

Conditions	Yield
With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In triethylamine at 20℃; for 27h; Arylation;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine Condensation;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at -78 - 20℃; for 13h; Sonogashira coupling;	90%

(3-iodo-pyridin-4-yl)-carbamic acid tert-butyl ester (211029-67-3) + prop-1-yne (74-99-7) → (3-prop-1-ynyl-pyridin-4-yl)-carbamic acid tert-butyl ester (211029-71-9)

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 20℃;	100%
Stage #1: (3-iodo-pyridin-4-yl)-carbamic acid tert-butyl ester; prop-1-yne; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In DMF (N,N-dimethyl-formamide); triethylamine at -78 - 20℃; Stage #2: With ammonium chloride In DMF (N,N-dimethyl-formamide); water; ethyl acetate; triethylamine	98%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at -78 - 20℃; for 5 - 6h;	97%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at -78 - 20℃; for 1h;

prop-1-yne (74-99-7) + 2,4-dibromo-6-pentyl-pyrimidine (494194-57-9) → 4-pentyl-2,6-di-prop-1-ynyl-pyrimidine (494194-56-8)

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

2,4-dibromo-pyrimidine (3921-01-5) + prop-1-yne (74-99-7) → 2,4-di-prop-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-methyl-pyrimidine (494194-61-5) + prop-1-yne (74-99-7) → 5-methyl-2,4-di-prop-1-ynyl-pyrimidine (494194-51-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 3h;	99%

2,4-dibromo-6-methyl-pyrimidine + prop-1-yne (74-99-7) → 4-methyl-2,6-di-prop-ynyl-pyrimidine (494194-53-5)

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

2,4-dibromo-5,6-dimethyl-pyrimidine (753470-32-5) + prop-1-yne (74-99-7) → 4,5-dimethyl-2,6-di-prop-1-ynyl-pyrinidine (494194-54-6)

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

4-(tert-butyldiphenylsilanyloxy)-2-butyn-1-al (112213-42-0) + prop-1-yne (74-99-7) → 1-(tert-butyldiphenylsilanyloxy)hepta-2,5-diyn-4-ol (874667-97-7)

Conditions	Yield
Stage #1: prop-1-yne With n-butyllithium; lithium bromide In tetrahydrofuran; hexane at -20℃; for 2h; Stage #2: 4-(tert-butyldiphenylsilanyloxy)-2-butyn-1-al In tetrahydrofuran; hexane at -20 - 20℃;	100%

prop-1-yne (74-99-7) + trimethylsilylacetylene (1066-54-2) → trimethyl(prop-1-ynyl)silane (6224-91-5)

Conditions	Yield
(Me2SiCp''2UBu)2O*2THF In tetrahydrofuran at 66℃; for 44h;	100%

2-bromo-6-fluorobenzaldehyde (360575-28-6) + prop-1-yne (74-99-7) → 2-fluoro-6-prop-1-ynylbenzaldehyde (608515-62-4)

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In DMF (N,N-dimethyl-formamide) at -78 - 20℃; for 4h;	100%

(η5-C5Me5)Nb(CO)4 (80432-28-6) + prop-1-yne (74-99-7) → C5(CH3)5Nb(HCCCH3)2CO

Conditions	Yield
In pentane byproducts: CO; Irradiation (UV/VIS); passing a faint stream of methylacetylene through Nb complex soln. under N2; irradiation (Hg medium pressure burner, 450 W), -20°C, 8-20 min; filtration; evapn. to dryness;	100%

C9H4F6INO2 (1139688-61-1) + prop-1-yne (74-99-7) → C12H7F6NO2 (1139688-65-5)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide Sonogashira coupling;	100%

(R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane (95337-97-6, 110171-85-2, 130659-83-5, 95338-04-8) + prop-1-yne (74-99-7) → (S)-1-((tert-butyldimethylsilyl)oxy)hept-5-yn-3-ol (960211-10-3)

Conditions	Yield
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere;	100%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78 - 0℃; for 2h;	85%
Stage #1: prop-1-yne With n-butyllithium In hexane at -78℃; for 0.0833333h; Stage #2: With potassium hexamethylsilazane In hexane; toluene at -78℃; for 0.5h; Stage #3: (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane; toluene at -78℃; for 2h;	83%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran at -78 - 0℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; water	80%

5-chloro-3-iodo-2-aminopyridine (211308-81-5) + prop-1-yne (74-99-7) → 5-chloro-3-prop-1-ynyl-pyridin-2-ylamine (1312755-53-5)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 0 - 20℃; for 1h;	100%

(R)-benzyl glycidol (14618-80-5) + prop-1-yne (74-99-7) → (2R)-1-(benzyloxy)hex-4-yn-2-ol (171075-74-4)

Conditions	Yield
Stage #1: prop-1-yne With n-butyllithium In hexane; toluene at 0℃; for 1.5h; Stage #2: With diethylaluminium chloride In hexane; toluene at 0℃; for 2h; Stage #3: (R)-benzyl glycidol In hexane; toluene for 0.166667h;	100%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78 - -40℃; for 0.666667h; Inert atmosphere; Stage #2: (R)-benzyl glycidol With boron trifluoride diethyl etherate In tetrahydrofuran; toluene at -78 - 0℃; Inert atmosphere;	98%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; 1,2-dimethoxyethane at -78 - -40℃; for 0.666667h; Inert atmosphere; Stage #2: (R)-benzyl glycidol With boron trifluoride diethyl etherate In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 1.16667h; Inert atmosphere;	98%

tert-butyl 4-azidopiperidine-1-carboxylate (180695-80-1) + prop-1-yne (74-99-7) → tert-butyl 4-(4-methyl-1H-1,2,3-triazol-1-yl)-piperidine-1-carboxylate

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20 - 40℃; for 5h; Sealed tube;	100%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 18h;	100%

prop-1-yne (74-99-7) + tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate (108492-14-4) → C15H26N4O4

Conditions	Yield
With copper diacetate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃;	100%

prop-1-yne (74-99-7) → 2-methyl-1-penten-3-yne (926-55-6)

Conditions	Yield
With methylaluminoxane In benzene-d6 at 20℃; under 1E-05 Torr; for 48h; Dimerization;	99.4%
With formaldehyd; palladium(II) acetylacetonate; triethylaluminum; triphenylphosphine In toluene at 100℃; for 6h;	44%
[(Et2N)3U][BPh4] In tetrahydrofuran-d8 at 110℃; for 24h; Dimerization;	94 % Chromat.

methanol (67-56-1) + carbon monoxide (201230-82-2) + prop-1-yne (74-99-7) → methacrylic acid methyl ester (80-62-6)

Conditions	Yield
With methanesulfonic acid; 2-(diphenylphosphino)pyridine; palladium diacetate at 45℃;	99%
With methanesulfonic acid; N,N-dimethyl-aniline; palladium complex with bis(3,5-dimethyl-4-methoxyphenyl) (6-methyl-2-pyridyl)phosphine at 65℃; for 7h; Product distribution / selectivity; Cooling with ethanol-dry ice; Autoclave;	73%
With methanesulfonic acid; 2-(diphenylphosphino)pyridine; palladium diacetate at 45℃; Mechanism; var. reagents and reaction conditions;

N-Methoxy-N-methyl-3-propyl-2-hexenamide (157731-55-0) + prop-1-yne (74-99-7) → 6-Propyl-5-nonen-2-yn-4-one (120696-27-7)

Conditions	Yield
With n-butyllithium; triphenylmethane 1.) -78 deg C, 15 min, 2.) r.t., 3 h;	99%

1,4-dihexyl-2,5-diiodobenzene (162715-91-5) + prop-1-yne (74-99-7) → 2,5-dihexyl-1,4-diprop-1-ynylbenzene (188781-60-4)

Conditions	Yield
With piperidine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride for 3h;	99%
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide under 760 Torr; for 4h;	82%

Ethyl 4-bromobenzoate (5798-75-4) + prop-1-yne (74-99-7) → ethyl 4-(prop-1-yn-1-29/122-yl)benzoate

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride 24 deg C, then 65 deg C;	99%

prop-1-yne (74-99-7) + (1R,2S,5R)-2-Methyl-5-((S)-(S)-3-oxiranyl-butyl)-6,8-dioxa-bicyclo[3.2.1]octane (585526-36-9) → (3S,4R)-3-Methyl-1-((1R,2S,5S)-2-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-yl)-oct-6-yn-4-ol (585526-37-0)

Conditions	Yield
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78 - 20℃;	99%

1-indoline (496-15-1) + prop-1-yne (74-99-7) → 4,4,6-trimethyl-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
With ammonium hexafluorophosphate; dodecacarbonyl-triangulo-triruthenium In benzene at 95℃; for 12h;	99%
With [(PCy3)2(CO)(CH3CN)2RuCCPh][BF4] In benzene-d6 at 80℃;	83 % Spectr.

(2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate (876288-81-2) + prop-1-yne (74-99-7) → (2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin (876288-82-3)

Conditions	Yield
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: (2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate In tetrahydrofuran at -78 - 24℃; for 3h;	99%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Stage #2: (2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate In tetrahydrofuran at -78 - 25℃; for 3h;	97%

Upstream product

• 110-86-1 pyridine 
• 590-93-2 2-Butynoic acid 
• 74-83-9 methyl bromide 
• 1066-26-8 sodium acetylide 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 10024-18-7 bromoallene 
• 13116-60-4 1,1,2,2-tetrachloropropane 
• 590-14-7 1-bromo-1-propene 
• 89123-63-7 3-bromo-2-methyl-2-propenoic acid 
• 498-23-7 citraconic acid 
• 463-49-0 1,2-propanediene 
• 594-20-7 2,2-dichloropropane 
• 557-93-7 2-bromoprop-1-ene 
• 5836-66-8 1,2-dibromo-3-methoxypropane 

Downstream Products

• 2916-31-6 2,2-dimethyl-1,3-dioxolane 
• 108-22-5 Isopropenyl acetate 
• 108-24-7 acetic anhydride 
• 67-64-1 acetone 
• 102654-22-8 isopropenyl-m-tolyl ether 
• 1568-83-8 2,2-bis(4-methoxyphenyl)propane 
• 102654-23-9 1-isopropenyloxy-2-methoxy-benzene 
• 627-09-8 Propargyl acetate 
• 590-38-5 2-methyl-3-pentyn-2-ol 
• 926-55-6 2-methyl-1-penten-3-yne 
• 63382-87-6 5,5-Dimethyl-2-mesityl-2-hexen-4-on 
• 63382-85-4 (E)-5,5-dimethyl-2-phenylhex-2-en-4-one 
• 67500-71-4 (E)-1-Adamantyl-3-phenyl-but-2-en-1-on 
• 67500-75-8 (E)-1-(2-Phenyl-1-adamantyl)-but-2-en-1-on 

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