23975-15-7

Usage

Uses

Used in Organic Synthesis:
Thiophene, 2,2'-(1,2-ethynediyl)bisis used as a building block in the synthesis of various organic compounds. Its unique aromatic properties and versatile chemical structure make it a valuable resource for creating new molecules with specific properties and functions.
Used in Chemical Reactions:
As a solvent, Thiophene, 2,2'-(1,2-ethynediyl)bisplays a crucial role in facilitating various chemical reactions. Its ability to dissolve a wide range of substances and its compatibility with different reaction conditions make it an ideal choice for many chemical processes.
Used in Pharmaceutical Industry:
Thiophene, 2,2'-(1,2-ethynediyl)bisis used as a component in the production of pharmaceuticals. Its unique chemical properties and reactivity make it suitable for the development of new drugs and therapeutic agents, contributing to the advancement of medical treatments.
Used in Agrochemical Industry:
In the agrochemical industry, Thiophene, 2,2'-(1,2-ethynediyl)bisis utilized in the synthesis of various agrochemicals, such as pesticides and herbicides. Its versatility and reactivity enable the development of effective and targeted chemical solutions for agricultural applications.
Used in Material Science:
Thiophene, 2,2'-(1,2-ethynediyl)bishas the potential to be utilized in the development of new materials and technologies. Its unique properties and reactivity make it a promising candidate for creating innovative materials with specific characteristics, such as conductivity, stability, or biocompatibility, for various applications in different industries.

Upstream product

• 1003-31-2 thiophene-2-carbonitrile 
• 928-49-4 hex-3-yne 
• 23229-66-5 2-prop-1-ynyl-thiophene 

Downstream Products

• 923567-30-0 [Ni(N₄C₂₀H₈(C(CSCHCHCH))2(C₆H₃(C(CH₃)3)2)2)] 
• 1173070-88-6 2,2',2'',2'''-(1-phenyl-1H-phosphole-2,3,4,5-tetrayl)tetrathiophene 
• 1198575-48-2 1-phenyl-3,4-di(thiophen-2-yl)isoquinoline 
• 1352928-86-9 dimethyl 3,4-di(thiophen-2-yl)phthalate 

Relevant academic research and scientific papers

Catalysts for the alkyne metathesis

Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.

Introducing a podand motif to alkyne metathesis catalyst design: A highly active multidentate molybdenum(VI) catalyst that resists alkyne polymerization

Podand prevents polymers: The molybdenum(VI) propylidyne catalyst 1 with a podand triphenolamine ligand shows high activity in the metathesis of a variety of alkyne substrates, including heterocycles that contain donor moieties. With one substrate-binding site blocked by the multidentate ligand, the undesired polymerization of small alkynes that occurs with non-podand-ligand complex 2 is completely inhibited. Copyright

Synthetic, mechanistic, and computational investigations of nitrile-alkyne cross-metathesis

The terminal nitride complexes NW(OC(CF3)2Me) 3(DME) (1-DME), [Li(DME)2][NW(OC(CF3) 2Me)4] (2), and [NW(OCMe2CF3) 3]3 (3) were prepared in good yield by salt elimination from [NWCl3]4. X-ray structures revealed that 1-DME and 2 are monomeric in the solid state. All three complexes catalyze the cross-metathesis of 3-hexyne with assorted nitriles to form propionitrile and the corresponding alkyne. Propylidyne and substituted benzylidyne complexes RCW(OC(CF3)2Me)3 were isolated in good yield upon reaction of 1-DME with 3-hexyne or 1-aryl-1-butyne. The corresponding reactions failed for 3. Instead, EtCW(OC(CF3)Me2) 3 (6) was prepared via the reaction of W2(OC(CF 3)Me2)6 with 3-hexyne at 95°C. Benzylidyne complexes of the form ArCW(OC(CF3)Me2)3 (Ar = aryl) then were prepared by treatment of 6 with the appropriate symmetrical alkyne ArCCAr. Three coupled cycles for the interconversion of 1-DME with the corresponding propylidyne and benzylidyne complexes via [2 + 2] cycloaddition-cycloreversion were examined for reversibility. Stoichiometric reactions revealed that both nitrile-alkyne cross-metathesis (NACM) cycles as well as the alkyne cross-metathesis (ACM) cycle operated reversibly in this system. With catalyst 3, depending on the aryl group used, at least one step in one of the NACM cycles was irreversible. In general, catalyst 1-DME afforded more rapid reaction than did 3 under comparable conditions. However, 3 displayed a slightly improved tolerance of polar functional groups than did 1-DME. For both 1-DME and 3, ACM is more rapid than NACM under typical conditions. Alkyne polymerization (AP) is a competing reaction with both 1-DME and 3. It can be suppressed but not entirely eliminated via manipulation of the catalyst concentration. As AP selectively removes 3-hexyne from the system, tandem NACM-ACM-AP can be used to prepare symmetrically substituted alkynes with good selectivity, including an arylene-ethynylene macrocycle. Alternatively, unsymmetrical alkynes of the form EtCCR (R variable) can be prepared with good selectivity via the reaction of RCN with excess 3-hexyne under conditions that suppress AP. DFT calculations support a [2 + 2] cycloaddition-cycloreversion mechanism analogous to that of alkyne metathesis. The barrier to azametalacyclobutadiene ring formation/breakup is greater than that for the corresponding metalacyclobutadiene. Two distinct high-energy azametalacyclobutadiene intermediates were found. These adopted a distorted square pyramidal geometry with significant bond localization.

Catalytic nitrile-alkyne cross-metathesis

The first catalytic cross-metathesis reaction of an alkyne with a nitrile is described. The nitride complex N≡W(OC(CF3)2CH3)3(DME) undergoes reversible triple-bond metathesis reactions with alkynes (RC≡CR; R = Et, 4-C6H4OMe), forming the alkylidyne complexes RC≡W(OC(CF3)2CH3)3(DME) (R = Et, 4-C6H4OMe) along with the corresponding nitrile RC≡N. This has been exploited to effect catalytic cross-metathesis of nitriles with alkynes, in which the organic CR fragments of two nitriles are coupled to yield an alkyne. A simple "sacrificial" alkyne (3-hexyne) acts as the N-atom acceptor, forming two equivalents of nitrile byproduct (propionitrile). Copyright

A highly active, heterogeneous catalyst for alkyne metathesis

(Chemical Equation Presented) An alkylidyne molybdenum amide complex is attached to nontoxic, amorphous silica to form a highly active, recyclable heterogeneous catalyst for alkyne metathesis. The catalyst does not undergo alkyne polymerization, can be utilized at a loading of 1 mol% at room temperature, and has shown unprecedented metathesis activity for the homodimerization of 2-propynylthiophene, a substrate that was previously problematic for alkyne metathesis.

HETEROGENEOUS ALKYNE METATHESIS

The present invention provides heterogeneous organometallic catalysts for alkyne metathesis, including the metathesis of internal alkynes. Organometallic precursors are covalently bonded to the oxygen atoms of metal oxide supports to form catalysts having carbyne functionality. The heterogeneous catalysts provide improved turn-over frequencies at lower reaction temperatures than conventional catalysts.