18887-49-5

Upstream product

• 18887-51-9 2,2'-Bis-acetoxymethyl-diphenylacetylen 
• 5159-41-1 2-iodobenzyl alcohol 
• 74-86-2 acetylene 
• 18887-52-0 2,2'-(ethyne-1,2-diyl)dibenzaldehyde 
• 10602-08-1 2-ethynylbenzyl alcohol 
• 18887-53-1 2-<2-<2-(Hydroxymethyl)phenyl>ethynyl>benzaldehyde 
• 38846-64-9 2-ethynylbenzaldehyde 
• 5865-77-0 1,1'-ethyne-1,2-diylbis[2-(bromomethyl)benzene] 
• 5294-03-1 di-o-tolylethyne 
• 6630-33-7 ortho-bromobenzaldehyde 
• 38399-13-2 2,2'-dibromotolane 

Downstream Products

• 19132-47-9 2,2'-Bis--cis-stilben 
• 19064-90-5 2-(2-hydroxymethylphenethyl)phenylmethanol 
• 286376-18-9 Bis(2-{[(trimethylsilyl)oxy]methyl}phenyl)acetylene 
• 5865-77-0 1,1'-ethyne-1,2-diylbis[2-(bromomethyl)benzene] 
• 286376-14-5 (Z)?(2?(isobenzofuran?1(3H)?ylidenemethyl)phenyl)methanol 
• 207673-28-7 Bis(2-{[(but-2-yn-1-yl)oxy]methyl}phenyl)acetylene 
• 431879-81-1 C₁₆H₁₂Cl₂ 
• 207673-27-6 Bis(2-{[(prop-2-yn-1-yl)oxy]methyl}phenyl)acetylene 
• 207673-31-2 Bis{2-[4-(trimethylsilyl)but-3-yn-1-yl]phenyl}acetylene 
• 207673-29-8 Bis[({[3-(trimethylsilyl)prop-2-yn-1-yl]oxy}methyl)phenyl]acetylene 
• 207673-32-3 2,2'-Di(but-2-yn-1-yl)-2,2'-{ethynediylbis[(2,1-phenylene)methylene]}dimalonate 
• 223596-84-7 Bis[2-(but-3-yn-1-yl)phenyl]acetylene 
• 1185105-96-7 (+)-N,N'-[ethyne-1,2-diylbis(benzene-2,1-diylmethanediyl)]bis{4-methyl-N-[(1R)-1-methylprop-2-yn-1-yl]benzenesulfonamide} 

Relevant academic research and scientific papers

Bridged tolanes: A twisted tale

The rotational motion of tolanes along their acetylene axis is not fully understood. What happens to the optical and electronic properties if the tolane backbone is forced into a twisted conformation? Several tethers were investigated to obtain tolanophan

Twisted tethered tolanes: Unanticipated long-lived phosphorescence at 77 K

Influencing the communication within a conjugated system as diphenylacetylene is a challenging subject in molecular electronics. Some examples of twisted tolanes are known, where high twists have been achieved in the solid state by steric encumbrance. The

Fluorescent signaling based on control of excited state dynamics. Biarylacetylene fluorescent chemosensors

We have previously reported that metal ion binding could restrict the excited state rotation of a biaryl chromophore, suppressing intersystem crossing and leading to increased emission. We have now applied the restriction of excited state dynamics to supp

Preparation of benzannulated spiroketals by gold(III) catalyzed spirocyclization of alkynyl diols

The first gold(III)-oxazoline catalysed intramolecular tandem dihydroalkoxylations of alkynyl diols to give benzannulated 5,6-spiroketal products is reported. The results showed that Au(III)-bisoxazoline (BOX) and Au(III)-pyridine-oxazoline complexes are highly efficient catalysts for such spirocyclizations. The mono- and dibenzannulated 5,6-spiroketals were obtained in high yields (> 90 %) by rapid conversion of symmetrical and nonsymmetrical alkynyl diols, respectively. The Au(III)-BOX-BF4 catalyst generated minor spirocyclization enantioselectivity (up to 6 % ee). The choice of solvent was important for the outcome of the reactions.

Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.

A straightforward double intramolecular cyclization of dibenzyl dichalcogenols into a triple bond

The intramolecular cyclizations of four types of dibenzyl chalcogenols, which contained one or two ethynyl groups, were carried out. Either the double 5-exo or 6-endo-dig mode ring closure reaction regio- and stereoselectively proceeded to give the corres

Novel π-conjugated cyclophanes: Magazine rack molecules

Synthesis of cyclophanes having alternating arylene-ethynylene as well as-ethenylene arrays is described. It is disclosed that these compounds are chiral on the basis of X-ray analysis and fluxional in solution on the basis of NMR spectra.

Synthesis of aromatic triynes as precursors to helicene derivatives

A general and versatile synthetic approach to a broad series of aromatic triynes as precursors to helicene derivatives has been developed. Employing a set of simple tools, triynes comprising the (phenylethynyl)benzene, 1-(phenylethynyl)naphthalene, and 1-(1-naphthylethynyl)-naphthalene moiety have been prepared in good to excellent yields throughout the whole reaction sequence. The methodology allows constructing various types of a junction between the central diarylacetylene moiety and the attached acetylene units to get the target triynes of general formula R-C≡C-CH2-X-CH2-Ar-C≡C-Ar-CH 2-X-CH2-C≡C-R or R-C≡C-CH2CH2-Ar-C=C-Ar-CH2CH 2-C≡C-R (R = H, CH3, TMS, or TIPS; X = O, NTs, or C(CO2CH3)2; Ar/Ar = 2-phenylene or 2-naphthylene).

Coupling reactions of ortho-substituted halobenzenes with alkynes. The synthesis of phenylacetylenes and symmetrical or unsymmetrical 1,2-diphenylacetylenes

The Pd- or Pd/Cu-catalyzed coupling reactions of halobenzenes bearing the methyl, hydroxymethyl, acetoxymethyl, methoxycarbonyl, or both methoxy and 4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl groups in the ortho-position with gaseous or metallated acetylene, (trialkylsilyl)acetylenes, and arylacetylenes have been systematically studied. Various functionalized aryl- or diarylacetylenes have been synthesized in good to excellent yields. Whereas additional fluoro, nitro, or methoxy group attached to the benzene ring does not interfere in the coupling reactions, the presence of a methoxycarbonyl requires a careful optimization of reaction conditions to achieve moderate yields.

Coupling reactions of ortho-substituted aryl halides with alkynes. The synthesis of functionalized 1-naphthyl-, 1-(1-naphthyl)-2-phenyl-, and 1,2- bis(1-naphthyl)acetylenes

Coupling of 2-functionalized 1-naphthyl halides with gaseous acetylene, (trialkylsilyl)acetylenes, and aryl acetylenes under Pd(PPh3)4 or Pd(PPh3)4/CuI catalysis has been investigated to prepare 1-naphthyl-, 1-