172264-69-6

Basic information

• Product Name: 2-Propyn-1-one, 1-(2-methylphenyl)-3-phenyl-
• Synonyms: 1-(o-tolyl)-3-phenyl-2-propynone;3-phenyl-1-(o-tolyl)prop-2-yn-1-one;1-(2-tolyl)-3-phenylprop-2-yn-1-one;3-Phenyl-1-o-tolyl-propynone;3-phenyl-1-o-tolylprop-2-yn-1-one;3-phenyl-1-o-tolylpropyn-1-one
• CAS NO: 172264-69-6
• Molecular Formula: C16H12O
• Molecular Weight: 220.271
• Mol File: 172264-69-6.mol

Chemical Properties

• CAS DataBase Reference: 2-Propyn-1-one, 1-(2-methylphenyl)-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propyn-1-one, 1-(2-methylphenyl)-3-phenyl-(172264-69-6)
• EPA Substance Registry System: 2-Propyn-1-one, 1-(2-methylphenyl)-3-phenyl-(172264-69-6)

Safety Data

• Hazardous Substances Data: 172264-69-6(Hazardous Substances Data)

Upstream product

• 933-88-0 ortho-toluoyl chloride 
• 615-37-2 ortho-methylphenyl iodide 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 479213-83-7 1-(2-methylphenyl)-3-phenyl-prop-2-yn-1-ol 
• 637-44-5 phenylpropyolic acid 
• 95-46-5 2-methylphenyl bromide 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 64-18-6 formic acid 
• 124-38-9 carbon dioxide 
• 635-26-7 o-tolylhydrazine hydrochloride 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 118-90-1 ortho-methylbenzoic acid 

Downstream Products

• 1458665-38-7 (2-phenyl-1H-pyrrol-3-yl)(o-tolyl)methanone 
• 65349-21-5 5-(2′-methylphenyl)-3-phenylisoxazole 
• 61001-55-6 3-(2?'-methylphenyl)-5-phenyl-1H-pyrazole 
• 57162-60-4 4-(2'-methylphenyl)-2,6-diphenylpyridine 
• 5448-38-4 N-benzyl-2-methylbenzamide 
• 61001-54-5 2-methyldibenzoylmethane 
• 100-47-0 benzonitrile 
• 1049685-64-4 1-acetyl-5-hydroxy-5-(2-methylphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 
• 5706-12-7 (E)-2-benzylidene-2,3-dihydro-1H-inden-1-one 
• 30069-65-9 3-phenylnaphthalen-1-ol 

Relevant articles and documents

Nickel (II) dibenzotetramethyltetraaza[14]annulene supported on DFNS nanoparticles catalyst in carbonylative sonogashira coupling

In this study, the carbonylative sonogashira coupling reaction was performed in the presence of CO (2 MPa) and Nitmtaa?DFNS as NPs. Nickel(II)dibenzotetramethyltetraaza[14]annulene complex (Nitmtaa) prepared and immobilized on amino-fucntionnalized DFNS (N-DFNS) via Ni[sbnd]N (NH2) bond to obtain a stable and reusable new nanocatalyst named as Nitmtaa?DFNS. Good to superb performance products were provided deploying Nitmtaa?DFNS nanocatalyst. In addition, the anatomy of Nitmtaa?DFNS has been distinguished by various methods, including XRD, VSM, FT-IR, SEM, EDX, TEM, and TGA. In addition, the hot filtration test provided complete insight into the heterogeneity of the catalyst. The reuse and recycling of the catalyst were repeatedly investigated for coupling reactions. In addition, the mechanism of the coupling reactions was thoroughly studied.

Electrochemical Palladium-Catalyzed Oxidative Sonogashira Carbonylation of Arylhydrazines and Alkynes to Ynones

Oxidative carbonylation using carbon monoxide has evolved as an attractive tool to valuable carbonyl-containing compounds, while mixing CO with a stoichiometric amount of a chemical oxidant especially oxygen is hazardous and limits its application in scale-up synthesis. By employing anodic oxidation, we developed an electrochemical palladium-catalyzed oxidative carbonylation of arylhydrazines with alkynes, which is regarded as an alternative supplement of the carbonylative Sonogashira reaction. Combining an undivided cell with constant current mode, oxygen-free conditions avoids the explosion hazard of CO. A diversity of ynones are efficiently obtained using accessible arylhydrazines and alkynes under copper-free conditions. A possible mechanism of the electrochemical Pd(0)/Pd(II) cycle is rationalized based upon cyclic voltammetry, kinetic studies, and intermediates experiments.

One-Pot Palladium-Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source

Carbonylation coupling reaction has emerged as a powerful and versatile strategy for the construction of carbonyl-containing compounds in modern synthetic chemistry over the past years. Carbon dioxide, a renewable one carbon molecule, has become one of the most attractive and promising alternative carbonyl sources due to its highly abundance, nontoxicity and stability in comparison with CO in recent years. However, in most cases, a two-chamber technique was generally necessary to allow the CO-producing and CO-consuming processes to perform successfully because of the complexities and incompatibility of reaction conditions, when carbon dioxide was utilized as carbonyl source. Herein, a practical one-pot protocol using carbon dioxide as the carbonyl source for the palladium-catalyzed carbonylative Sonogashira coupling has been established, providing an expedient and practical route to a wide range of functionalized alkynones and indoxyls under mild reaction conditions. By finding a suitable catalytic system, the method allowed the CO-generating and CO-consuming processes to proceed in one pot, wherein carbon monoxide was generated in situ from the reduction of carbon dioxide in the absence of any fluoride reagents. Simple and safe operation, readily available substrates, good functional group tolerance and mild reaction conditions are the features of the method.

Solvent switchable Pd/DNA catalyst in carbonylative Sonogashira coupling

Palladium catalysts immobilized on DNA (Pd/DNA) were applied for the first time in the carbonylative Sonogashira coupling, at 1 atm of CO. Different alkynones were obtained with a high yield in DMF. In the presence of water, the selectivity completely changed and diaryl alkynes, typical Sonogashira products, were selectively formed. In addition to Pd/DNA, soluble palladium species also participated in the catalytic process. The stability of the catalytic system increased after the addition of DNA excess.

Pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex and preparation and application thereof

The invention relates to a pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex. The pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex is prepared from benzimidazole serving as a skeleton and pyridine serving

Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source

Abstract: A practical and efficient palladium-catalyzed carbonylative Sonogashira cross-coupling reaction for the synthesis of alkynones from aryl iodides, alkynes, and formic acid as the CO source has been described. Under the assistance of PPh3/I2, formic acid can be used as the CO source for synthesis of alkynones in moderate–good yields. Furthermore, it is also successfully applied for the modification of natural products, such as vindoline and tabersonin, to obtain the corresponding products.

Carbonylative Sonogashira Coupling of Aryl Iodides with Terminal Alkynes Catalyzed by Palladium Nanoparticles

A convenient and efficient method for the synthesis of α,β-alkynyl ketones from the three-component coupling of aryl iodides, terminal alkynes, and carbon monoxide (carbonylative Sonogashira coupling reaction) is successfully developed. The carbonylative Sonogashira coupling reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles to produce the corresponding α,β-alkynyl ketones in good to excellent yields.

Combining Electronic and Steric Effects to Generate Hindered Propargylic Alcohols in High Enantiomeric Excess

Tethered ruthenium-TsDPEN complexes have been applied to the catalysis of the asymmetric transfer hydrogenation of a range of aryl/acetylenic ketones. The introduction of an ortho- substituent to the aryl ring of the substrate results in a reversal of the

A polysalen based on polyacylamide stabilized palladium nanoparticle catalyst for efficient carbonylative Sonogashira reaction in aqueous media

A highly cross-linked polymer matrix polysalen based on acrylamide and N,N'-methylene-bisacrylamide (NNMBA) was successfully prepared. It has been proved that this type of polysalen is an effective support for immobilizing palladium complex. The polysalen may provide coordination sites for conjugation with a palladium catalyst to produce polysalen-Pd catalyst. The polysalen-Pd was firstly applied in phosphine-free carbonylative Sonogashira coupling reactions of aryl iodides with terminal alkynes to produce α,β-alkynyl ketones in 81-95% yields in aqueous media, which was much higher than that of homogeneous Pd-salen in 52% yield. Furthermore, the catalyst showed excellent recyclability without any significant loss in its activity.

Palladium-catalyzed carbonylative Sonogashira coupling of aryl diazonium salts with formic acid as the CO source: The effect of 1,3-butadiene

An efficient carbonylative cross-coupling of aryl diazonium salts with terminal alkynes using formic acid as the CO source has been developed. Various useful alkynones were produced in moderate to good yields. Notably, 1,3-butadiene was found to play a crucial role in this transformation.