5768-10-5

Usage

Uses

Used in Materials Science:
1,4-BIS(1-HYDROXYCYCLOHEXYL)-1,3-BUTADIYNE is used as a key component in the development of materials with specialized properties. Its diacetylene nature allows for the creation of photoresponsive polymers and liquid crystals, which can change their properties in response to light or other stimuli.
Used in Nanotechnology:
In the field of nanotechnology, 1,4-BIS(1-HYDROXYCYCLOHEXYL)-1,3-BUTADIYNE is utilized in the synthesis of functionalized carbon nanotubes. These nanotubes have a wide range of applications, from electronics to medicine, due to their unique strength, flexibility, and electrical conductivity.
Used in Drug Delivery:
1,4-BIS(1-HYDROXYCYCLOHEXYL)-1,3-BUTADIYNE also has potential applications in drug delivery systems. Its unique structure can be harnessed to develop new methods for delivering therapeutic agents, potentially improving the efficacy and targeting of treatments.
It is important to handle 1,4-BIS(1-HYDROXYCYCLOHEXYL)-1,3-BUTADIYNE with care due to its potential hazards, and further research is needed to fully explore and understand its applications and properties.

InChI:InChI=1/C14H16N4S/c1-10-13(15-14(19)17-16-10)9-6-11-4-7-12(8-5-11)18(2)3/h4-9H,1-3H3,(H,15,17,19)

Upstream product

• 108-94-1 cyclohexanone 
• 821-10-3 1,4-Dichloro-2-butyne 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 460-12-8 Butadiyne 
• 90086-65-0 1-(2-Iodoethynyl)-1-cyclohexanol 
• 766-85-8 3-methoxy-1-iodobenzene 
• 13957-27-2 1-(2-bromoethynyl)cyclohexanol 
• 536-74-3 phenylacetylene 
• 1066-54-2 trimethylsilylacetylene 
• 693-02-7 hex-1-yne 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 927-74-2 3-Butyn-1-ol 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 6712-35-2 2-phenylpent-4-yn-2-ol 

Downstream Products

• 122447-41-0 1,3'-bis-(4-chloro-phenyl)-5,5'-bis-(1-hydroxy-cyclohexyl)-1H,3'H-[4,4']bi[1,2,3]triazolyl 
• 122766-36-3 4-(1-hydroxy-cyclohexyl)-5-(1-hydroxy-cyclohexylethynyl)-1-(4-nitro-phenyl)-1H-[1,2,3]triazole 
• 99413-16-8 1,4-tris(1-acetoxy-1-cyclohexyl)-1,3-butadiyne 
• 102075-07-0 3-chloro-1,4-di-cyclohex-1-enyl-but-3-en-2-one 
• 113795-83-8 [5,5'-bis-(1-hydroxy-cyclohexyl)-[4,4']bi[1,2,3]triazolyl-1,3'-diyl]-di-acetic acid diethyl ester 
• 2979-05-7 di-cyclohex-1-enyl-butadiyne 
• 6165-44-2 1,4-dicyclohexyl-butane 
• 74347-26-5 1-[4-(1-hydroxycyclohexyl)butyl]cyclohexanol 
• 99413-17-9 1,1,6,6-dipentamethylene-3,4-diethyl-1,2,4,5-hexatetraene 
• 101880-70-0 1-acetoxy-1-(4-cyclohexyl-butyl)-cyclohexane 
• 102464-00-6 1,4-bis-(1-acetoxy-cyclohexyl)-butane 
• 112323-59-8 [5,5'-bis-(1-hydroxy-cyclohexyl)-[4,4']bi[1,2,3]triazolyl-1,3'-diyl]-di-acetic acid 
• 110051-74-6 [5,5'-bis-(1-hydroxy-cyclohexyl)-[4,4']bi[1,2,3]triazolyl-1,3'-diyl]-di-acetic acid diamide 
• 122146-00-3 5,5'-bis-(1-hydroxy-cyclohexyl)-3'-(4-nitro-phenyl)-1-phenyl-1H,3'H-[4,4']bi[1,2,3]triazolyl 

Relevant academic research and scientific papers

Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling

Glycosyl triazoles have been introduced as efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect t

Strategy to isolate ionic gold sites on silica surface: Increasing their efficiency as catalyst for the formation of 1,3-diynes

A new strategy is presented to obtain an efficient heterogeneous gold catalyst constituted by isolated ionic gold sites, which is known to be effective in alkyne coupling reaction. The procedure is based on a significant difference between offered gold amount and available adsorbent sites on the support, ensuring the formation of very active isolated gold ion sites. In order to achieve this purpose, mesoporous silica xerogel was grafted with an ionic silsesquioxane containing charged ammonium quaternary group. The modified silica showed 0.25 mmol of cationic sites per gram of material and presented thermal stability up to 200 °C. This material was applied as support for immobilization of Au(III) ions as square planar AuCl4? complex. The gold amount offered was just 12 % of the exchangeable capacity. The catalyst was efficiently applied in the cross coupling reactions, in which only 0.22 mol% was applied to obtain symmetric and non-symmetric 1,3-diynes.

Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach

Due to the high oxidation potential between AuI and AuIII, gold redox catalysis requires at least stoichiometric amounts of a strong oxidant. We herein report the first example of an electrochemical approach in promoting gold-catalyzed oxidative coupling of terminal alkynes. Oxidation of AuI to AuIII was successfully achieved through anode oxidation, which enabled facile access to either symmetrical or unsymmetrical conjugated diynes through homo-coupling or cross-coupling. This report extends the reaction scope of this transformation to substrates that are not compatible with strong chemical oxidants and potentiates the versatility of gold redox chemistry through the utilization of electrochemical oxidative conditions.

Polymer-Supported Cu–Nanoparticle as an Efficient and Recyclable Catalyst for Oxidative Homocoupling of Terminal Alkynes

Abstract: Copper nanoparticle on polyaniline support was synthesised by using in situ polymerisation and composite formation technique. This metal polymer nanocomposites material is found to be efficient for homocoupling of terminal alkynes which afford s

Ester functionalized hydrophobic task specific ionic liquid for Glaser coupling

A new hydrophobic ester functionalized task specific ionic liquid has been synthesized and its application explored in the synthesis of conjugated 1,3-diynes through Glaser coupling of terminal alkynes. Terminal alkynes undergo oxidativecoupling smoothly

Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide

Bisphosphorylallenes were easily obtained in multigram scale from the Wittig-type rearrangement of bispropargyl alcohols. Unlike other conjugated bis-allenes, these reagents underwent a double cyclization mediated by iodine or copper dibromide leading to the formation of bis-1,2-oxaphospholenes.

Copper catalyzed oxidative homocoupling of terminal alkynes to 1,3-diynes: A Cu3(BTC)2 MOF as an efficient and ligand free catalyst for Glaser-Hay coupling

A straightforward and efficient method has been demonstrated for the oxidative coupling of terminal alkynes using a simple Cu3(BTC)2-metal organic framework as a sustainable heterogeneous copper catalyst. A series of symmetrical 1,3-diynes bearing diverse functional groups have been synthesized in moderate to excellent yields via a Cu3(BTC)2 catalyzed Glaser-Hay reaction. The presence of the coordinatively unsaturated open CuII sites in Cu3(BTC)2 catalyzes the homocoupling in the presence of air, as an environment friendly oxidant without the use of external oxidants, ligands or any additives. The present methodology avoids stoichiometric reagents and harsher or special reaction conditions, and shows good functional group tolerance. The as-prepared catalyst could be separated easily by simple filtration and reused several times without any notable loss in activity. The hot filtration test has investigated the true heterogeneity of the catalyst. Additionally, the powder X-ray diffraction pattern of the reused catalyst revealed the high stability of the catalyst.

Ionic liquid-promoted Copper(II)-Catalyzed homocoupling of terminal alkynes in aqueous phase or under solvent-limited conditions

A reusable ionic liquid 1-butyl-3-methylimidazolium bromide/Cu(II) system was proven to be a reusable catalyst for the homocoupling of terminal alkynes at mild temperature using air as oxidant in aqueous phase or under solvent-limited conditions. In most cases, good to excellent yields can be achieved, either aromatic alkynes or aliphatic alkynes were used as substrates. The homocoupling products 1,3-diynes were separated by extraction from the reaction system. And the activity of residue showed it could be reused for 3 and 6 cycles respectively under the aqueous phase conditions and solventlimited conditions. Furthermore, this reaction can be easily scaled up to gram level.

A theophylline based copper: N -heterocyclic carbene complex: Synthesis and activity studies in green media

The synthesis of an easily accessible theophylline-derived copper complex with additional ammonium functionalization has been developed. This xanthine-based metal compound turned out to be an active initiator of the alkyne-azide cycloaddition reaction (CuAAC) and Glaser homo-coupling reaction in aqueous media at room temperature.

Transition metal-free dimerization of alkynes using hypervalent iodine reagents

This communication describes the use of hypervalent iodine reagents to facilitate the homo-coupling of terminal alkynes. A variety of different aliphatic and aromatic alkynes were successfully dimerized when using acetoxy-benziodoxole as the activating agent under operationally simple transition metal-free conditions.