17553-35-4

Usage

Type of compound

linear alkyne

Number of methyl groups attached to the carbon backbone

eight

Industrial applications

used as a precursor for the synthesis of other organic compounds, important building block for the production of specialty chemicals and pharmaceuticals

Reactivity

high

Handling

handled with care in laboratory and industrial settings

InChI:InChI=1/C18H30/c1-15(2,3)11-13-17(7,8)18(9,10)14-12-16(4,5)6/h1-10H3

Upstream product

• 17553-43-4 2-chloro-2,5,5-trimethyl-hex-3-yne 
• 75-16-1 methylmagnesium bromide 
• 1522-16-3 2,5,5-trimethyl-hex-3-yn-2-ol 

Relevant academic research and scientific papers

THE CONFORMATIONS AND VIBRATIONAL SPECTRA OF 2,2,5,5,6,6,9,9-OCTAMETHYL-3,7-DECADIYNE

The IR spectra of the title compound as a solute in various solvents, as a melt and as a crystalline solid have been recorded.Raman spectra of the solutions, the melt and of the crystalline solid were obtained and semiquantitative polarization measurements carried out.The data have been interpreted in terms of one conformer (anti) present in the crystal.In the melt and in solutions an additional conformer (gauche) was present in low abundance, probably between 5 and 10percent, and ΔH0 (gauche -> anti) was estimated to be -7.9 +/- 2 kJ mol-1.Spectral correlations with the related molecule, 1,5-hexadiyne are pointed out.

A Convenient Synthesis of 1,2-Dithietes and 1,2-Dithioxo Compounds Stabilized by Buttressing and Resonance Effects, Respectively, by Sulfuration of Alkynes with Elemental Sulfur

Sulfuration of a series of alkynes by elemental sulfur was investigated.Alkynes carrying highly bulky substituents, 2,2,5,5-tetramethyl-3-hexyne (6a), 1,2-di-(1-adamantyl)ethyne (6b), 3,3-dimethyl-1-phenyl-1-butyne (6c), and 1-(1-adamantyl)-2-phenylethyne (6d), reacted with sulfur to give the corresponding stable 1,2-dithietes 7a-d in 46-65percent yields.Less hindered alkynes reacted with sulfur to afford 1,4-dithiins and thiophenes as the final products which were derived from the initial products, 1,2-dithietes, via their tautomerization to the corresponding 1,2-dithioxo compounds, while extremely congested alkynes failed to react with sulfur even under forcing conditions.On the other hand, ynamines, a typical electron-rich alkyne, 1-diethylamino-2-phenylthioethyne (6o), 1-diethylamino-2-phenylselenoethyne (6p), and tetraethylethynediamine (6q) were sulfurated under milder conditions to afford resonance-stabilized 1,2-dithioxo compounds 19o-q as the principal products.Mechanism of the formation of 1,2-dithietes, 1,2-dithioxo compounds, and other products is discussed.