136612-72-1

Basic information

• Product Name: Benzene, 1,1'-(1E)-1-buten-3-yne-1,4-diylbis[4-methyl-
• CAS NO: 136612-72-1
• Molecular Formula: C18H16
• Molecular Weight: 232.325
• Mol File: 136612-72-1.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-(1E)-1-buten-3-yne-1,4-diylbis[4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-(1E)-1-buten-3-yne-1,4-diylbis[4-methyl-(136612-72-1)
• EPA Substance Registry System: Benzene, 1,1'-(1E)-1-buten-3-yne-1,4-diylbis[4-methyl-(136612-72-1)

Safety Data

• Hazardous Substances Data: 136612-72-1(Hazardous Substances Data)

Upstream product

• 22666-07-5 di-p-tolylbutadiyne 
• 60655-80-3 (E)-4-methylstyrenyl bromide 
• 156423-16-4 (E)-1-(2-iodovinyl)-4-methylbenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 2227-58-9 3-(4-methylphenyl)prop-2-ynoic acid 
• 56578-35-9 4-methyl-cinnamaldehyde 
• 5142-75-6 tri(p-tolyl)bismuth 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 
• 142025-09-0 C₂₂H₂₄Te 

Relevant articles and documents

A series of pincer-ligated rhodium complexes as catalysts for the dimerization of terminal alkynes

A series of pincer complexes of Rh has been prepared and tested as catalysts for the dimerization of terminal alkynes. The pincers included aryl/bis(phosphinite) POCOP, aryl/bis(phosphine) PCP, and diarylamido/bis(phosphine) PNP ligands. RhI co

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.

One-pot synthesis of α,β-unsaturated ketones through sequential alkyne dimerization/hydration reactions using the Hoveyda-Grubbs catalyst

Herein we report a sequential one-pot alkyne dimerization/hydration protocol for the regioselective synthesis of α,β-unsaturated ketones in quantitative yields. The alkyne dimerization reactions of terminal arylacetylenes proceeded with high regioselectivity in the presence of the Hoveyda-Grubbs 2nd generation catalyst (1 mol%) and tricyclohexylphosphine (4 mol%). The hydration reactions ofin situformed 1-aryl-3-en-1-ynes proceeded very rapidly in the presence of CCl3COOH/p-TsOH·H2O, yielding the corresponding unsaturated ketones within 15 minutes in quantitative yields. Different arylacetylene derivatives were converted to the corresponding α,β-unsaturated ketones in quantitative yields (94-95%) using sequential one-pot alkyne dimerization/hydration reactions.

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.

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,

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

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

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.

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