264135-64-0

Basic information

• Product Name: Ethanone, 1-[4-(1-octynyl)phenyl]-
• CAS NO: 264135-64-0
• Molecular Formula: C16H20O
• Molecular Weight: 228.334
• Mol File: 264135-64-0.mol

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-[4-(1-octynyl)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-[4-(1-octynyl)phenyl]-(264135-64-0)
• EPA Substance Registry System: Ethanone, 1-[4-(1-octynyl)phenyl]-(264135-64-0)

Safety Data

• Hazardous Substances Data: 264135-64-0(Hazardous Substances Data)

Upstream product

• 15719-55-8 trimethyl(oct-1-yn-1-yl)silane 
• 109613-00-5 4-acetophenyl triflate 
• 629-05-0 n-octyne 
• 99-90-1 para-bromoacetophenone 
• 13329-40-3 4-Iodoacetophenone 
• 99-91-2 para-chloroacetophenone 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 

Relevant articles and documents

A Waste-Minimized Approach to Cassar-Heck Reaction Based on POLITAG-Pd0 Heterogeneous Catalyst and Recoverable Acetonitrile Azeotrope

Three different Pd0-based heterogeneous catalysts were developed and tested in the Cassar–Heck reaction (i. e., copper-free Sonogashira reaction) aiming at the definition of a waste minimized protocol. The cross-linked polymeric supports used in this investigation were designed to be adequate for different reaction media and were decorated with different pincer-type ionic ligands having the role of stabilizing the formation and dimension of palladium nanoparticles. Among the ionic tags tested, bis-imidazolium showed the best performances in terms of efficiency and durability of the metal catalytic system. Eventually, aqueous acetonitrile azeotrope was selected as the reaction medium as it allowed the best catalytic efficiency combined with easy recovery and reuse. Finally, the synergy between the selected catalyst and reaction medium allowed to obtain highly satisfactory isolated yields of a variety of substrates while using a low amount of metal catalyst. The high performance of the designed POLymeric Ionic TAG (POLITAG)-Pd0, along with its good selectivity achieved in a copper-free process, also led to a simplified purification procedure allowing the minimization of the waste generated as also proven by the very low E-factor values (1.4–5) associated.

An efficient nanocluster catalyst for Sonogashira reaction

Pd together with CuI has been well known as the catalyst towards Sonogashira reaction, which provides an effective route to functional alkynes. However, the achievement of high activity and selectivity of this catalytic system is still challenging in some cases. Illustrative examples include their low activity for aryl chloride substrates, and switched selectivity to oxidative coupling products in air atmosphere. In this work, a Cu-incorporated Au13 nanocluster [Au13Cu2(PPh3)6(SC2H4Ph)6]+[NO3]- (Au13Cu2) was designed and prepared in high yield via rapid synthesis. This atomically precise nanocluster shows the potential to be a novel catalytic system for Sonogashira reaction, featuring high activity and selectivity, as well as good recyclability even in air atmosphere.

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

Palladium(II) complex for catalyzing sonogashira coupling reactions and a method thereof

A palladium(II) complex which catalyzes the Sonogashira coupling reaction efficiently under aerobic condition and a method of employing the palladium(II) complex to synthesize internal alkynes. The palladium(II) complex is an effective catalyst for the co

Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the p

γ-Valerolactone as an alternative biomass-derived medium for the Sonogashira reaction

γ-Valerolactone (GVL) can be used as an efficient and practical alternative to the banned and commonly used dipolar aprotic solvents. In this contribution GVL has been used as a non-toxic, biodegradable, biomass-derived medium, for the definition of a sim

Aqueous Sonogashira coupling of aryl halides with 1-alkynes under mild conditions: Use of surfactants in cross-coupling reactions

Aqueous Sonogashira coupling between lipophilic terminal alkynes and aryl bromides or iodides gave moderate to high yields at 40°C using readily available and inexpensive surfactants (2.0 w/v% in water) such as SDS and CTAB. The catalyst precursor was 2 m

MCM-41-immobilized Schiff base-pyridine bidentate copper(I) complex as a highly efficient and recyclable catalyst for the Sonogashira reaction

Abstract A novel MCM-41-immobilized Schiff base-pyridine bidentate copper(I) complex [MCM-41-Sb,Py-CuI] was conveniently prepared from commercially available and inexpensive 3-aminopropyltriethoxysilane via immobilization on MCM-41, followed by reacting w

Synthesis of unsymmetrically disubstituted ethynes by the palladium/copper(I)-cocatalyzed sila-Sonogashira-Hagihara coupling reactions of alkynylsilanes with aryl iodides, bromides, and chlorides through a direct activation of a carbon-silicon bond

In this paper, we explore the copper/palladium-cocatalyzed cross-coupling reactions of 1-aryl-2-trimethylsilylethynes with aryl iodides, bromides, and chlorides as coupling partners, to furnish unsymmetrically disubstituted ethynes in moderate to excellent yields. Various aryl iodides were subjected to reaction under the optimized conditions with 5 mol % of Pd(PPh3) 2 and 50 mol % of CuCl. The steric properties of the aryl iodide proved more influential to the outcome of the cross-coupling reaction than electronic factors. In addition, we succeeded in synthesizing unsymmetrical diarylethynes using two different aryl iodides in one-pot. Furthermore, under the same reaction conditions with 10 mol % of PdCl2, 40 mol % of P(4-FC6H4)3, and 50 mol % of CuCl as catalyst, we succeeded in synthesizing unsymmetrical diarylethynes from various aryl bromides. Finally, we explored reactions with aryl chlorides and duly discovered that unsymmetrical diarylethynes were obtainable in moderate to good yields when 10 mol % of Pd(OAc)2, 10 mol % of (-)-DIOP, and 10 mol % of CuCl were used. These reactions proceed through a direct activation of a carbon-silicon bond in alkynylsilanes by CuCl to generate the corresponding alkynylcopper species via transmetalation from silicon to copper. Mechanistic investigations on the reaction of alkynylsilanes with aryl bromides confirmed that the trimethylsilyl bromide generated in situ retarded both transmetalation steps between CuCl and alkynylsilane, and between palladium(II) species formed by oxidative addition and alkynylcopper species.

1,2,3-Triazol-5-ylidene-palladium complex catalyzed Mizoroki-Heck and Sonogashira coupling reactions

The bis-1,4-dimesityl-1,2,3-triazol-5-ylidene-palladium complex (1a) successfully catalyzes the Mizoroki-Heck and Sonogashira coupling reactions with aryl bromides to give the corresponding alkenes and alkynes, respectively, in good to excellent yields. In the Mizoroki-Heck reaction, electron-rich, electron-poor, and functionalized aryl bromides and alkenes are tolerated, while the substrates are limited to electron-poor aryl halides in the Sonogashira coupling reaction. The palladium complex also catalyzes cross-coupling reactions with aryl chlorides to give higher yields of products than does the bis-IMes-Pd complex analogue (2), under specific conditions.