Production Method 1

89343-06-6

82192-57-2

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -82 °C; 2 h, -82 °C
1.2 -82 °C; -82 °C → rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Sulfur mediated propargylic C-H alkylation of alkynes

Hu, Gang; et al, Organic Chemistry Frontiers, 2018, 5(14), 2167-2170

Production Method 2

80522-42-5

82192-57-2

Reaction Conditions

1.1 Catalysts: Butyllithium Solvents: Diethyl ether ;  -40 °C → 0 °C

Reference

Triisopropylsilyl Trifluoromethanesulfonate

Hua, Duy H.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 3

82192-57-2

Reaction Conditions

1.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Toluene

Reference

Palladium-Catalyzed Reductive Homocoupling Reaction of 3-Silylpropargyl Carbonates. New Entry into Allene-Yne Compounds

Ogoshi, Sensuke; et al, Journal of Organic Chemistry, 1995, 60(14), 4650-2

Production Method 4

104493-07-4

82192-57-2

Reaction Conditions

1.1 Reagents: Pyridine Solvents: Diethyl ether
2.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Toluene

Reference

Palladium-Catalyzed Reductive Homocoupling Reaction of 3-Silylpropargyl Carbonates. New Entry into Allene-Yne Compounds

Ogoshi, Sensuke; et al, Journal of Organic Chemistry, 1995, 60(14), 4650-2

Production Method 5

13154-24-0

6089-04-9

82192-57-2

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane
1.2 Solvents: Tetrahydrofuran
2.1 Solvents: Ethanol
3.1 Reagents: Pyridine Solvents: Diethyl ether
4.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Toluene

Reference

Palladium-Catalyzed Reductive Homocoupling Reaction of 3-Silylpropargyl Carbonates. New Entry into Allene-Yne Compounds

Ogoshi, Sensuke; et al, Journal of Organic Chemistry, 1995, 60(14), 4650-2

Production Method 6

82192-57-2

Reaction Conditions

1.1 Reagents: Magnesium bromide ,  4,4,5,5-Tetramethyl-2-(1E)-1-octen-1-yl-1,3,2-dioxaborolane Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ;  0 °C; 1 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C
2.2 Reagents: Ammonium chloride Solvents: Water

Reference

Regio- and stereoselective synthesis of 1,4-enynes by iron-catalysed Suzuki-Miyaura coupling of propargyl electrophiles under ligand-free conditions

Agata, Ryosuke; et al, Organic & Biomolecular Chemistry, 2020, 18(16), 3022-3026

Production Method 7

89343-06-6

82192-57-2

Reaction Conditions

1.1 Reagents: tert-Butyllithium Solvents: Tetrahydrofuran

Reference

Cycloaddition-based approaches to nor-taxoids and aphenes via magnesium- and indium-mediated reactions (MSc Thesis)

Husk, Elizabeth, 2004, , ,

Production Method 8

13154-24-0

82192-57-2

Reaction Conditions

1.1 Reagents: Ethyl bromide ,  Magnesium Solvents: Tetrahydrofuran
1.2 -

Reference

The hydroboration of silylacetylenes. The "silyl-Markovnikov" hydroboration route to pure (Z)-1-(2-borylvinyl)silanes and β-keto silanes

Soderquist, John A.; et al, Journal of the American Chemical Society, 1989, 111(13), 4873-8

Production Method 9

13154-24-0

82192-57-2

Reaction Conditions

Reference

3-Lithio-1-triisopropylsilyl-1-propyne

Ruecker, Christoph, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-3

Production Method 10

5633-34-1

89343-06-6

82192-57-2

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Cesium fluoride Catalysts: Palladium, bis(acetonitrile)dichloro- ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-bis(1,1-dimethylethyl)phosphine Solvents: Toluene ;  48 h, 100 °C

Reference

Palladium-Catalyzed Methylation of Alkynyl C(sp)-H Bonds with Dimethyl Sulfonium Ylides

Liu, Yan-Yun; et al, Journal of Organic Chemistry, 2013, 78(20), 10421-10426

Production Method 11

343967-13-5

4529-04-8

82192-57-2

Reaction Conditions

1.1 Solvents: Diethyl ether

Reference

Useful synthetic reagents derived from 1-(triisopropylsilyl)propyne and 1,3-bis(triisopropylsilyl)propyne. Direct, stereoselective synthesis of either Z or E enynes

Corey, E. J.; et al, Tetrahedron Letters, 1982, 23(7), 719-22

Production Method 12

80522-42-5

82192-57-2

Reaction Conditions

Reference

3-Lithio-1-triisopropylsilyl-1-propyne

Ruecker, Christoph, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-3

Production Method 13

167275-08-3

82192-57-2

Reaction Conditions

1.1 Solvents: Ethanol
2.1 Reagents: Pyridine Solvents: Diethyl ether
3.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Toluene

Reference

Palladium-Catalyzed Reductive Homocoupling Reaction of 3-Silylpropargyl Carbonates. New Entry into Allene-Yne Compounds

Ogoshi, Sensuke; et al, Journal of Organic Chemistry, 1995, 60(14), 4650-2

Production Method 14

86950-97-2

105746-54-1

104465-98-7

82192-57-2

Reaction Conditions

1.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Regio- and stereoselective synthesis of 1,4-enynes by iron-catalysed Suzuki-Miyaura coupling of propargyl electrophiles under ligand-free conditions

Agata, Ryosuke; et al, Organic & Biomolecular Chemistry, 2020, 18(16), 3022-3026

Production Method 15

51751-87-2

82192-57-2

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  rt; 4 h, 50 °C
2.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C
2.2 Reagents: Ammonium chloride Solvents: Water

Reference

Regio- and stereoselective synthesis of 1,4-enynes by iron-catalysed Suzuki-Miyaura coupling of propargyl electrophiles under ligand-free conditions

Agata, Ryosuke; et al, Organic & Biomolecular Chemistry, 2020, 18(16), 3022-3026

Production Method 16

104493-07-4

82192-57-2

Reaction Conditions

1.1 Reagents: Pyridine Solvents: Dichloromethane ;  0 °C; overnight, rt
2.1 Reagents: Magnesium bromide ,  4,4,5,5-Tetramethyl-2-(1E)-1-octen-1-yl-1,3,2-dioxaborolane Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ;  0 °C; 1 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C
3.2 Reagents: Ammonium chloride Solvents: Water

Reference

Regio- and stereoselective synthesis of 1,4-enynes by iron-catalysed Suzuki-Miyaura coupling of propargyl electrophiles under ligand-free conditions

Agata, Ryosuke; et al, Organic & Biomolecular Chemistry, 2020, 18(16), 3022-3026

1-(Triisopropylsilyl)-1-propyne Raw materials

• Magnesium, (1E)-1-octenylbromo-
• 1-Octene, 1-bromo-, (1E)-
• 4-[6-(propan-2-yl)-1H-benzimidazol-2-yl]aniline
• Triisopropylsilyl trifluoromethanesulfonate
• Triisopropylsilylacetylene
• chlorotris(propan-2-yl)silane
• Silane, tris(1-methylethyl)[(trifluoromethyl)sulfonyl]-
• 3-[Tris(1-methylethyl)silyl]-2-propyn-1-ol
• Lithium,1-propynyl- (6CI,7CI,8CI,9CI)
• Magnesium, (1Z)-1-octen-1-ylbromo-
• Silane, (3-bromo-1-propynyl)tris(1-methylethyl)-
• 2H-Pyran, tetrahydro-2-[[3-[tris(1-methylethyl)silyl]-2-propyn-1-yl]oxy]-
• 2-(2-Propynyloxy)tetrahydropyran

1-(Triisopropylsilyl)-1-propyne Preparation Products

• 1-(Triisopropylsilyl)-1-propyne (82192-57-2)

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• Solvents and Organic Chemicals Organic Compounds Organometallic compounds Organometalloid compounds Organosilicon compounds Alkylsilanes
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

• 125251-42-5(Silane, 1,3-butadiyne-1,4-diylbis[tris(1-methylethyl)-)
• 55630-45-0(Silane, (1,1-dimethylethyl)dimethyl-1-propynyl-)
• 918871-51-9(2-Propyn-1-amine, 3-[tris(1-methylethyl)silyl]-)
• 89343-06-6(Triisopropylsilylacetylene)
• 111409-80-4(Silane, 1,3,5-hexatriyne-1,6-diylbis[tris(1-methylethyl)-)
• 82192-58-3(Lithium, [3-[tris(1-methylethyl)silyl]-2-propynyl]-)
• 920282-98-0(Silane, trimethyl[8-[tris(1-methylethyl)silyl]-1,3,5,7-octatetrayn-1-yl]-)
• 920282-74-2(Silane, trimethyl[4-[tris(1-methylethyl)silyl]-1,3-butadiyn-1-yl]-)
• 87350-60-5(Magnesium, bromo[3-[tris(1-methylethyl)silyl]-2-propynyl]-)
• 121143-01-9(Silane, tris(1-methylethyl)-1-pentynyl-)