1-Octyne

Base Information

• Chemical Name: 1-Octyne
• CAS No.: 629-05-0
• Molecular Formula: C8H14
• Molecular Weight: 110.199
• Hs Code.: 29012980
• European Community (EC) Number: 211-069-3
• UNII: 7S3FMU8W67
• DSSTox Substance ID: DTXSID9060863
• Nikkaji Number: J21.021H
• Wikidata: Q161668
• Mol file: 629-05-0.mol

Synonyms:1-octyne;oct-1-yne

Chemical Property of 1-Octyne

Chemical Property:

• Appearance/Colour: clear colourless to yellow liquid
• Vapor Pressure: 37.7 mm Hg ( 37.7 °C)
• Melting Point: -80 °C
• Refractive Index: n20/D 1.416(lit.)
• Boiling Point: 126.027 °C at 760 mmHg
• Flash Point: 17.778 °C
• PSA: 0.00000
• Density: 0.763 g/cm³
• LogP: 2.59000
• Storage Temp.: Flammables area
• Solubility.: 0.024g/l
• Water Solubility.: Miscible with alcohol, ether and other organic solvents. Immiscible with water.
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 110.109550447
• Heavy Atom Count: 8
• Complexity: 73.3

Purity/Quality:

99.9% ^*data from raw suppliers

1-Octyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,Xi
• Hazard Codes: F,Xn,Xi
• Statements: 11-65-36/37/38
• Safety Statements: 16-62-33-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: CCCCCCC#C
• General Description: 1-Octyne, also known as 1-Octine, Hexylacetylene, or n-Hexylacetylene, is a terminal alkyne that serves as a valuable substrate in transition-metal-free silylzincation and silaboration reactions, as well as in copper-catalyzed silylstannylation. It reacts with silylboranes and dialkylzinc under optimized conditions to form silylzincated intermediates, which can be further functionalized. Additionally, in copper-catalyzed three-component couplings, 1-octyne exhibits inverse regioselectivity, yielding products with the stannyl group predominantly at the terminal carbon, highlighting its versatility in synthesizing functionalized alkenes.

Technology Process of 1-Octyne

There total 58 articles about 1-Octyne which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

oct-1-yn-3-yl benzoate (196302-07-5) → n-octyne (629-05-0) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

tris(2,2'-bipyridine)nickel(II) tetrafluoroborate; In N,N-dimethyl-formamide; Ambient temperature; electrolysis;

DOI:10.1016/S0040-4039(97)01396-8

Reference yield: 95.0%

1,2-dibromooctane (152212-49-2,152212-73-2,6269-92-7) → n-octyne (629-05-0)

Guidance literature:

With potassium hydroxide; tetraoctyl ammonium bromide; In Petroleum ether; at 90 ℃; for 6h;

DOI:10.1016/S0040-4020(01)98925-2

Reference yield: 92.0%

(Z)-1-bromo-1-octene (42843-49-2) → n-octyne (629-05-0)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In Petroleum ether; at 25 ℃; for 2h;

upstream raw materials:

oct-2-yne

1-bromo-hexane

acetylenemagnesium bromide

sodium acetylide

Downstream raw materials:

1,1,1,3-tetrachlorononane

Non-2-yn-1-al diethyl acetal

octadec-7-yne

(+/)-dec-3-yn-2-ol

Refernces

In Situ Generation of Silylzinc by Si?B Bond Activation Enabling Silylzincation and Silaboration of Terminal Alkynes

10.1002/anie.201802887

The research presents a novel protocol for the in-situ generation of unstable silylzinc species through the reaction of dialkylzinc, phosphine, and silylborane. This method enables highly controllable regio-, stereo-, and chemoselective silylzincation and silaboration of terminal alkynes without the need for a transition-metal catalyst. The researchers optimized the conditions using 1-octyne, PhMe2Si–B(pin), and Me2Zn in THF, finding that the addition of a small amount of phosphine was crucial for smooth silylzincation. The resultant silylzincated intermediates can be utilized as vinyl anion equivalents for further chemical transformations. The study also explores the silaboration reaction via Zn–B exchange, yielding silaboration products that serve as versatile platforms for obtaining densely functionalized vinylsilanes and vinylborons.

Inverse regioselectivity in the silylstannylation of alkynes and allenes: Copper-catalyzed three-component coupling with a silylborane and a tin alkoxide

10.1039/c5cc01856k

The research investigates the copper-catalyzed three-component coupling of silylboranes and tin alkoxides with alkynes and allenes for silylstannylation, aiming to explore an alternative to conventional palladium-catalyzed silylstannylation and achieve inverse regioselectivity. The study found that in the presence of a Cu(I) catalyst, specifically CuCl with P(tBu)3 in acetonitrile, the silylstannylation of terminal alkynes and allenes proceeded with high yields and inverse regioselectivity compared to palladium-catalyzed processes. For instance, 1-octyne reacted with PhMe2Si–B(pin) and Bu3SnOtBu to produce products with the stannyl group predominantly attached to the terminal carbon of the alkyne. The research concluded that this copper-catalyzed method provides a convenient and direct route to synthesize 2-silyl-1-stannyl-1-alkenes and 1-silyl-2-stannyl-2-alkenes with high synthetic utility, demonstrating high functional group compatibility and the potential for further applications in organic synthesis.

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