Production Method 1

621-62-5

927-80-0

Reaction Conditions

Reference

Ethoxyacetylene

Caster, Kenneth C., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2005, 1, 1-6

Production Method 2

621-62-5

927-80-0

Reaction Conditions

1.1 Reagents: Butyllithium ,  Diethylamine Solvents: Tetrahydrofuran
1.2 Reagents: Sodium chloride Solvents: Water

Reference

A convenient procedure for the preparation of ethoxyacetylene and ethoxyethynyl carbinols

Raucher, Stanley; Bray, Brian L., Journal of Organic Chemistry, 1987, 52(11), 2332-3

Production Method 3

16339-88-1

927-80-0

Reaction Conditions

1.1 Reagents: Potassium hydroxide ;  100 °C

Reference

Studies on volatile plant substances. CXV. Synthesis of 3-methylcitral stereoisomers by the Arens and van Dorp reaction

Naves, Yves Rene; Ardizio, Pierre, Bulletin de la Societe Chimique de France, 1951, 374, 374-7

Production Method 4

621-62-5

927-80-0

Reaction Conditions

1.1 Reagents: Butyllithium ,  Diethylamine Solvents: Tetrahydrofuran ,  Hexane ;  5 min, 0 °C
1.2 30 min, 0 °C

Reference

Enzymatic hydrolysis and synthesis of chrysanthemic acid esters

Sukumaran, Joly; van Gool, Jacqueline; Hanefeld, Ulf, Enzyme and Microbial Technology, 2005, 37(2), 254-260

Production Method 5

593-92-0

927-80-0

Reaction Conditions

1.1 Reagents: 2,2′-Bipyridine ,  Cuprous iodide ,  Tripotassium phosphate Solvents: Toluene ;  2 d, 110 °C; 110 °C → rt
1.2 Reagents: Potassium tert-butoxide Solvents: 1,4-Dioxane ;  overnight, rt

Reference

HOTf-Catalyzed, Solvent-Free Oxyarylation of Ynol Ethers and Thioethers

Hu, Liang; Gui, Qingwen; Chen, Xiang; Tan, Ze; Zhu, Gangguo, Journal of Organic Chemistry, 2016, 81(11), 4861-4868

Production Method 6

23521-49-5

927-80-0

Reaction Conditions

Reference

Product subclass 2: 1-(organooxy)alk-1-ynes and 1-(heterooxy)alk-1-ynes

Witulski, B.; Alayrac, C., Science of Synthesis, 2006, 24, 933-956

Production Method 7

927-80-0

Reaction Conditions

Reference

Hydrohalogenation of metallized alkoxyacetylenes

Kazankova, M. A.; Ilyushin, V. A.; Lutsenko, I. F., Zhurnal Obshchei Khimii, 1980, 50(3), 690-1

Production Method 8

2678-54-8

927-80-0

Reaction Conditions

1.1 Reagents: Sodium amide Solvents: Diethyl ether ;  8 h, reflux

Reference

The chemistry of the alkali amides

Bergstrom, F. W.; Fernelius, W. Conard, Chem. Rev., 1933, 12, 43-179

Production Method 9

927-80-0

Reaction Conditions

Reference

Synthesis and Thermolysis of Enediynyl Ethyl Ethers as Precursors of Enyne-Ketenes

Tarli, Anna; Wang, Kung K., Journal of Organic Chemistry, 1997, 62(25), 8841-8847

Production Method 10

31612-88-1

927-80-0

Reaction Conditions

1.1 Reagents: Nitrogen oxide (N2O4) Solvents: Diethyl ether ,  Hexane ;  -78 °C; -78 °C → rt

Reference

The behaviors of metal acetylides with dinitrogen tetroxide

Woltermann, Christopher J.; Shechter, Harold, Helvetica Chimica Acta, 2005, 88(2), 354-369

Production Method 11

621-62-5

927-80-0

Reaction Conditions

1.1 Reagents: Sodium ,  Ferric nitrate Solvents: Ammonia ;  20 min, -70 °C; -70 °C → rt
1.2 Reagents: Sodium chloride Solvents: Water ;  -70 °C

Reference

Combined epimerization and acylation: Meerwein-Ponndorf-Verley-Oppenauer catalysts in action

Klomp, Dirk; Djanashvili, Kristina; Svennum, Nina Cianfanelli; Chantapariyavat, Nuttanun; Wong, Chung-Sing; et al, Organic & Biomolecular Chemistry, 2005, 3(3), 483-489

Production Method 12

2032-35-1

927-80-0

Reaction Conditions

1.1 Reagents: Sodium amide ,  Ferric nitrate Solvents: Ammonia

Reference

Synthesis of an Acid-Labile seco-Cl-Acetal for a Selective Tumor Therapy through Radical Synthesis Methodology

Starck, Dorothea, 1993, , ,

Production Method 13

621-62-5

927-80-0

Reaction Conditions

1.1 Reagents: Sodium Catalysts: Iron nitrate (Fe(NO3)3) nonahydrate Solvents: Ammonia

Reference

A high yielding, reproducible synthesis of trimethylsilylketene

Black, T. Howard; Farrell, John R.; Probst, Donald A.; Zotz, Michael C., Synthetic Communications, 2002, 32(13), 2083-2088

Production Method 14

18519-95-4

927-80-0

Reaction Conditions

Reference

Applications of phase transfer catalysis. Part 19. A convenient route to alkynes via phase transfer catalysis

Dehmlow, Eckehard V.; Lissel, Manfred, Tetrahedron, 1981, 37(9), 1653-8

Production Method 15

621-62-5

927-80-0

Reaction Conditions

1.1 Reagents: Sodium amide ,  Ferric nitrate Solvents: Ammonia ,  Water

Reference

Ethoxyacetylene

Jones, E. R. H.; Eglinton, Geoffrey; Whiting, M. C.; Shaw, B. L., Organic Syntheses, 1954, 34, 46-9

Production Method 16

16339-88-1

927-80-0

Reaction Conditions

Reference

Acetylenic ethers. II. Ethoxy- and butoxyacetylene

Jacobs, Thomas L.; Cramer, Richard; Hanson, John E., Journal of the American Chemical Society, 1942, 64, 223-6

Production Method 17

23679-22-3

927-80-0

Reaction Conditions

Reference

Ethynyl ethers and thioethers as synthetic intermediates

Arens, J. F., Advances Org. Chem. Methods Results (Ralph A. Raphael, 1960, 2, 117-212

Production Method 18

23679-21-2

927-80-0

Reaction Conditions

Reference

The chemistry of acetylenic ethers. XI. Preparation of acetylenic ethers from aldehydes

Arens, J. F., Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, 1955, 74, 271-6

Production Method 19

621-62-5

927-80-0

Reaction Conditions

Reference

Product subclass 5: sodium-nitrogen compounds

Jonczyk, A.; Kowalkowska, A., Science of Synthesis, 2006, 8, 1141-1195

Production Method 20

2983-26-8

927-80-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Hexamethylphosphoramide

Reference

Dehydrobromination of 1,2-dibromoethyoxyethane using various amine bases

Stalick, Wayne M.; Khorrami, Ali; Hatton, Kimi S., Journal of Organic Chemistry, 1986, 51(19), 3577-81

Ethoxyacetylene Raw materials

• 2-Bromo-1,1-diethoxyethane
• 1,2-Dibromo-1-ethoxyethane
• Chloroacetaldehyde Diethyl Acetal
• Ethene, 1,1-dibromo-(9CI)
• cis-2-chlorovinyl ethyl ether
• (E)-1-chloro-2-ethoxyethene
• Ethene, 1-bromo-2-ethoxy-, (1E)-
• Lithium, (ethoxyethynyl)-
• 1,1-Diethoxyethene
• Cis-1-Bromo-2-ethoxyethylene
• Ethene, 1-bromo-2-ethoxy-

Ethoxyacetylene Preparation Products

• Ethoxyacetylene (927-80-0)

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• Solvents and Organic Chemicals Organic Compounds Acids/Esters
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

• 925892-82-6(Ethyne, 1,2-diethoxy-)
• 101537-27-3(1,2-Bis(ethynyloxy)ethane)
• 73506-39-5(Sodium ethoxyacetylide)
• 42842-08-0
• 31612-88-1(Lithium, (ethoxyethynyl)-)
• 977-80-0(Pregn-4-ene-3,20-dione,17-chloro-6a-fluoro- (7CI,8CI))
• 36678-63-4(Magnesium, bromo(ethoxyethynyl)-)
• 960205-17-8(2-(2-(Ethynyloxy)ethoxy)ethan-1-ol)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)