3031-68-3

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Hexadiyne-1,6-diol is used as a starting material in the synthesis of thiarubrine A, an antibiotic with potential applications in treating bacterial infections.
Used in Chemical Synthesis:
2,4-Hexadiyne-1,6-diol is also used to synthesize the disodium salt of 2,4-hexadiyne 1,6-disulfate (HDDS), which may have various applications in different industries, such as in the production of specialty chemicals or materials.

InChI:InChI=1/C6H6O2/c7-5-3-1-2-4-6-8/h7-8H,5-6H2

Upstream product

• 50-00-0 formaldehyd 
• 460-12-8 Butadiyne 
• 107-19-7 propargyl alcohol 
• 1725-82-2 3-iodo-2-propyn-1-ol 
• 821-10-3 1,4-Dichloro-2-butyne 
• 764-93-2 1-decyne 
• 629-74-3 hexadec-1-yne 
• 765-03-7 1-dodecyne 
• 765-10-6 1-tetradecyne 
• 629-89-0 1-octadecyne 
• 536-74-3 phenylacetylene 
• 622-79-7 benzyl azide 
• 2708-97-6 5,6-diiodo-1,2,3,4-tetrafluorobenzene 
• 64695-78-9 1,2-difluoro-4,5-dibromobenzene 

Downstream Products

• 32527-15-4 1,6-bis(p-toluenesulfonyloxy)-2,4-hexadiyne 
• 629-11-8 1,6-hexanediol 
• 107550-83-4 (2E,4E)-hexa-2,4-diene-1,6-diol 
• 16260-59-6 1,6-dichlorohexa-2,4-diyne 
• 114611-41-5 6-hydroxy-2,4-hexadiynyl 1,2-diphenylcyclopropene-3-carboxylate 
• 114611-42-6 2,4-hexadiynylene di(1,2-diphenylcyclopropene-3-carboxylate) 
• 70287-75-1 2,4-hexadiynylene-di-p-fluorobenzene sulfonate 
• 135201-57-9 1-(4-fluorobenzenesulfonyloxy)-2,4-hexadiyn-6-ol 
• 114843-16-2 hexadiynedial 
• 110-54-3 hexane 
• 111-27-3 hexan-1-ol 
• 627907-86-2 C₃₄H₂₈N₂O₆ 
• 1048333-63-6 6-hydroxy-hexa-2,4-diynyl 4-hexyloxybenzoate 

Relevant academic research and scientific papers

Features of the mechanism of oxidative dehydrodimerization of propynol

Analysis of kinetic regularities for the propynol oxidative coupling under the action of cupric salts in pyridine and in the presence of a buffer is undertaken. The reaction mechanism, including the formation of Cu(I) acetylides, is considered.

Mechanistic investigation and further optimization of the aqueous Glaser-Hay bioconjugation

The Glaser-Hay bioconjugation has recently emerged as an efficient and attractive method to generate stable, useful bioconjugates with numerous applications, specifically in the field of therapeutics. Herein, we investigate the mechanism of the aqueous Glaser-Hay coupling to better understand optimization strategies. In doing so, it was identified that catalase is able to minimize protein oxidation and improve coupling efficiency, suggesting that hydrogen peroxide is produced during the aqueous Glaser-Hay bioconjugation. Further, several new ligands were investigated to minimize protein oxidation and maximize coupling efficiency. Finally, two novel strategies to streamline the Glaser-Hay bioconjugation and eliminate the need for secondary purification have been developed.

First total synthesis of acetylenic alcohol 15-methyltricosa-2,4-diyne-1, 6-diol (strongylodiol-G) derived from marine sponge

The first total and efficient synthesis of a naturally occurring acetylenic alcohol 15-methyltricosa-2,4-diyne-1,6-diol (strongylodiol-G) derived from marine sponge involving nine steps has been described. 1-Bromo-9- methyloctadecane (5) and hex-6-tetrahydropyranyloxyhex-2,4-diyn-1-al (9) which were initially synthesised separately starting from 1,8-octanediol (1) and propargyl alcohol (6), respectively, have been used as the final intermediates to obtain the title compound. The key steps in the synthesis involved ionic liquid-mediated bromination of 1,8-octanediol (1), tetrahydropyranylation of 8-bromooctan-1-ol (2) using acidic ionic liquid [bmim]HSO4 and monotetrahydropyranylation of hex-2,4-yn-1,6-diol (7) using ultrasonic energy.

Glaser coupling reaction in supercritical carbon dioxide

It is demonstrated for the first time that Glaser coupling can be carried out smoothly in supercritical carbon dioxide using a solid base (NaOAc) instead of amines.

Noncatalytic, solvent-free thermal formation of cyclic trimers using 1,6-bis(acyloxymethyl)hexa-2,4-diyne derivatives

The thermal reactivity of diacetylenes in the liquid phase was studied extensively to elucidate the cooperative mechanism of polymerization.

Catalytically active self-assembled silica-based nanostructures containing supported nanoparticles

Self-assembled tubular silica-based nanostructures can be prepared using a simple, low-energy intensive and benign protocol under mild conditions (100 °C) using microwave irradiation and conventional heating. These nanotubes were found to contain metal nanoparticles that are catalytically active in the microwave-assisted homocoupling of terminal alkynes. The Royal Society of Chemistry 2010.

Glaser oxidative coupling in ionic liquids: An improved synthesis of conjugated 1,3-diynes

Terminal alkynes undergo oxidative-coupling smoothly in the presence of the CuCl-TMEDA catalytic system in hydrophobic [bmim]PF6 ionic liquid under aerobic conditions to produce 1,3-diynes in excellent yields under mild conditions. The substrates, alkynes, show enhanced reactivity and selectivity in ionic liquids (ILs). The recovery of the catalyst is facilitated by the hydrophobic nature of the [bmim]PF6 ionic liquid.

Leaf-like CuO nanosheets on rGO as an efficient heterogeneous catalyst for Csp-Csp homocoupling of terminal alkynes

In this work, the economic and well-defined leaf-like CuO nanosheets on rGO (CuO nanosheets/rGO) was synthesized by a convenient hydrothermal method. The morphology and chemical composition of CuO nanosheets/rGO were confirmed by XRD, SEM-EDS, TEM, HR-TEM, and XPS techniques. The CuO nanosheets/rGO was successfully applied as a high-performance heterogeneous catalyst in the homocoupling of 12 terminal alkynes, and the isolated yield of each product was more than 80%, except for propargyl alcohol. This catalyst could be reused five times with little activity loss. Thus, it is beneficial for green and sustainable development of organic synthetic chemistry.

In the optically-multiplexed-

A method for optical super-multiplexing using polyynes to provide enhanced images from stimulated Raman microscopy is disclosed. In some exemplary embodiments, the polyynes are organelle-targeted or spectral barcoded. Imaging can be enhanced by using the polyynes to image whole live cells or specific organelles within live cells. The polyynes can also be used in optical data storage (i.e., encoding) and identification (i.e., decoding) applications.

Synthesis of ene-yne-enes by nickel-catalyzed double SN2′ substitution of 1,6-dichlorohexa-2,4-diyne

1,6-Dichlorohexa-2,4-diyne undergoes nickel-catalyzed double substitution with aryl and alkenyl Grignard reagents to provide substituted ene-yne-enes. The reaction is formally an extension of the well-described SN2′-allylic and -propargylic substitution reactions but the mechanism is considerably more complex. The products might function as building blocks for conjugated polymers.