136612-76-5

Basic information

• Product Name: Benzene, 1,1'-[(1E)-1-buten-3-yne-1,4-diyl]bis[4-methoxy-
• CAS NO: 136612-76-5
• Molecular Formula: C18H16O2
• Molecular Weight: 264.324
• Mol File: 136612-76-5.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-[(1E)-1-buten-3-yne-1,4-diyl]bis[4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[(1E)-1-buten-3-yne-1,4-diyl]bis[4-methoxy-(136612-76-5)
• EPA Substance Registry System: Benzene, 1,1'-[(1E)-1-buten-3-yne-1,4-diyl]bis[4-methoxy-(136612-76-5)

Safety Data

• Hazardous Substances Data: 136612-76-5(Hazardous Substances Data)

Upstream product

• 768-60-5 4-methoxyphenylacetylen 
• 1066-54-2 trimethylsilylacetylene 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 696-62-8 para-iodoanisole 
• 136618-41-2 E-2'-p-methoxystyryl iodide 
• 22779-05-1 1,4-bis(4-methoxyphenyl)-1,3-butadiyne 
• 142025-10-3 C₂₂H₂₄O₂Te 

Downstream Products

• 1200397-53-0 (E)-1,4-bis(4-methoxyphenyl)but-3-en-1-one 
• 878652-50-7 (Z)-1,4-bis(4-methoxyphenyl)but-2-ene-1,4-dione 

Relevant articles and documents

Stereo- A nd regioselective dimerization of alkynes to enynes by bimetallic syn-carbopalladation

Enynes are important motifs in bioactive compounds. They can be synthesized by alkynea'alkyne couplings for which a number of mechanisms have been suggested depending on catalyst type and dominant product isomers. Regarding bimetallic pathways, hydrometalations and anti-carbopalladations have been discussed to account for the formation of geminally substituted and (Z)-configured enynes, respectively. Here we report a bimetallic alkynea'alkyne coupling that yields (E)-configured enynes. An unusual type of acetylide Pd bridging was found in putative catalytic intermediates which is arguably responsible for the regio- A nd stereochemical reaction outcome. Mechanistic studies suggest that a double μa'κ:η2 acetylide bridging enables a bimetallic syn-carbometalation. Interestingly, depending on the reaction conditions, it is also possible to form the geminal regioisomer as major product with the same catalyst. This regiodivergent outcome is explained by bi-versus monometallic reaction pathways.

Palladium-Catalyzed Decarboxylative Homodimerization of Propiolic Acids: Synthesis of 1,3-Enynes

The 1,3-enyne product was obtained as a result of a decarboxylative homodimerization reaction when a variety aryl propiolic acids were reacted in the presence of Pd(TFA)2/i-PrPPh2 and K2CO3. It was found that aryl propiolic acids bearing an electrondonating substituent provided the desired product; however, aryl propiolic acids an bearing electron-withdrawing substituent did not give the desired product.

Coordination chemistry of H-spirophosphorane ligands towards pentacarbonylchlororhenium(I) – synthesis, structure and catalytic activity of complexes

Synthesis of a group of carbonyl rhenium coordination compounds with hydrospirophosphorane ligands was carried out and described. Different symmetrical HP(OCH2CH2NH)2L1, HP(OCH2CMe2NH)2L2,

Ligand-Controlled Diastereoselective Cobalt-Catalysed Hydroalkynylation of Terminal Alkynes to E- or Z-1,3-Enynes

A diastereoselective hydroalkynylation of terminal alkynes to form the head-to-head dimerization products by two different cobalt-phosphine catalyst system is reported. The use of the bidentate ligand dppp and additional triphenylphosphine led to the selective formation of the (E)-1,3-enynes (E:Z>99:1) in good to excellent yields, while the tridentate ligand TriPhos led to the corresponding (Z)-1,3-enynes in moderate to good yields with excellent stereoselectivities (up to E:Z=1:99). Both pre-catalysts are easy to handle, because of their stability under atmospheric conditions. The optimized reaction conditions were identified by the Design of Experiments (DoE) approach, which has not been used before in cobalt-catalysed reaction optimisation. DoE decreased the number of required reactions to a minimum.

A K-arylacetylide complex for catalytic terminal alkyne functionalization using KO: TBu as a precatalyst

Herein we report a transition metal free catalytic terminal alkyne functionalization across the C-X triple bond (X = CH and N) with E-selective homo (alkyne-alkyne) and head-to-tail selective hetero (alkyne-nitrile) dimerization. A series of stoichiometric reactions enabled us to crystallize a reactive organometallic intermediate K-arylacetylide complex which was characterized by X-ray crystallography, indicating that an ionic mechanism is operative.

Sequential Transformation of Terminal Alkynes to 1,3-Dienes by a Cooperative Cobalt Pyridonate Catalyst

We describe the cobalt(II) catalyst 1 bearing a phosphinopyridonate ligand for sequential transformation of aryl terminal alkynes to (E,Z)-1,3-dienes with excellent stereoselectivity. By cooperative metal-ligand reactivity, 1 reacts readily with the termi

Photochemical Cobalt-Catalyzed Hydroalkynylation to Form 1,3-Enynes

A photochemical hydroalkynylation is reported employing a metallaphotoredox approach using cobalt catalysis and an organic dye, 4CzIPN. The protocol enables catalysis without the need for stoichiometric metal reductants, normally needed to convert higher

Selective dimerization of terminal acetylenes in the presence of PEPPSI precatalysts and relative chloro- and hydroxo-bridged N-heterocyclic carbene palladium dimers

Highly regio- and stereoselective dimerization of terminal acetylenes occurs in the presence of [PdCl2(IPr)(3-chloropyridine)], other members of the family of PEPPSI precatalysts and the structurally related N-heterocyclic carbene palladium dim

Platinum Complexes Bearing Bulky N-Heterocyclic Carbene Ligands as Efficient Catalysts for the Fully Selective Dimerization of Terminal Alkynes

New platinum(0) complexes of the general formula [(NHC)Pt(dvtms)] (dvtms=1,3-divinyltetramethyldisiloxane) containing bulky N-heterocyclic carbene (NHC) ligands were prepared, characterized, and found to be catalytically active in the fully regio- and ste

Kinetics and Mechanistic Insights into the Acetate-Assisted Dimerization of Terminal Alkynes under Ruthenium- and Acid-Promoted (RAP) Catalysis

The mechanism of the dimerization of terminal aryl alkynes promoted by [{RuCl(μ-Cl)(η6-p-cymene)}2](1)/AcOH, under cooperative transition metal/Br?nsted acid catalysis, has been investigated with regard to (i) the activation of the d