22682-29-7

Basic information

• Product Name: 2-METHYLBENZOPHENONE
• Synonyms: 2-PHENYL TOLYL KETONE;2-PHENYL CARBONYL TOLUENE;O-METHYLBENZOPHENONE
• CAS NO: 22682-29-7
• Molecular Formula: C₁₅H₁₄O
• Molecular Weight: 196.24
• Mol File: 22682-29-7.mol

Chemical Properties

• Melting Point: -18 °C
• Boiling Point: 125-127 °C0.3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.083 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.5958(lit.)
• CAS DataBase Reference: 2-METHYLBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLBENZOPHENONE(22682-29-7)
• EPA Substance Registry System: 2-METHYLBENZOPHENONE(22682-29-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22682-29-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H14O/c1-11-6-5-8-13(10-11)15(16)14-9-4-3-7-12(14)2/h3-10H,1-2H3

Upstream product

• 529-19-1 2-Methylbenzonitrile 
• 591-17-3 meta-bromotoluene 
• 201230-82-2 carbon monoxide 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 
• 937-01-9 trimethyl(3-methylphenyl)stannane 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 17113-82-5 1-methyl-2-(trimethylstannyl)benzene 
• 933-88-0 ortho-toluoyl chloride 
• 932-31-0 ortho-tolylmagnesium bromide 
• 4792-30-7 3-methylphthalic acid anhydride 
• 620-22-4 3-Methylbenzonitrile 
• 33872-80-9 o-tolyl magnesium chloride 
• 1711-06-4 3-Methylbenzoyl chloride 
• 16419-60-6 2-Methylphenylboronic acid 

Downstream Products

• 90445-45-7 3-(m-tolyl)isobenzofuran-1(3H)-one 
• 84-54-8 2-methylanthracene-9,10-dione 
• 2159-37-7 carboxy-2 methyl-3' benzophenone 
• 90445-42-4 2-(3-methylbenzoyl)benzaldehyde 
• 4091-00-3 C₁₅H₁₀O₅ 
• 137381-65-8 3-[3-(2-Imidazol-1-yl-ethyl)-4-oxo-3,4-dihydro-phthalazin-1-yl]-benzoic acid ethyl ester 
• 137382-63-9 3-(4-Oxo-3,4-dihydro-phthalazin-1-yl)-benzoic acid ethyl ester 
• 152567-99-2 3-(4-Oxo-3,4-dihydro-phthalazin-1-yl)-benzoic acid 

Relevant articles and documents

Transition-metal-free carbonylation of aryl halides with arylboronic acids by utilizing stoichiometric CHCl3 as the carbon monoxide-precursor

Under transition-metal-free conditions, carbonylative Suzuki couplings of aryl halides with arylboronic acid using stoichiometric CHCl3 as the carbonyl source has been developed. The simple, efficient, and environmentally benign method was successfully applied to the synthesis of Fenofibric acid, naphthyl phenstatin, and carbon-13 labeled biaryl ketone.

Redox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis

Palladium/norbornene (Pd/NBE) cooperative catalysis, also known as the Catellani reaction, has become an increasingly useful method for site-selective arene functionalization; however, certain constraints still exist because of its intrinsic mechanistic pathway. Herein, we report a redox-neutral ortho functionalization of aryl boroxines via Pd/NBE catalysis. An electrophile, such as carboxylic acid anhydrides or O-benzoyl hydroxylamines, is coupled at the boroxine ortho position, and a proton as the second electrophile is introduced at the ipso position. This reaction does not require extra oxidants or reductants and avoids stoichiometric bases or acids, thereby tolerating a wide range of functional groups. In particular, orthogonal chemoselectivity between aryl iodide and boroxine moieties is demonstrated, which could be used to control reaction sequences. Finally, a deuterium-labeling study supports the ipso protonation pathway. This unique mechanistic feature could inspire the development of a new class of Pd/NBE-catalyzed transformations.Poly-substituted aromatics are ubiquitously found in drugs and agrochemicals. To realize streamlined synthesis, it is highly attractive if functional groups can be site-selectively introduced at unactivated positions with common arene starting materials. Here, a method is developed to directly introduce acyl and amino groups at unactivated ortho positions of readily available aryl boron compounds. Compared with the known ortho functionalization approaches, this method does not require stoichiometric bases, external oxidants, or reductants. Consequently, the reaction is chemoselective: a wide range of functional groups, including highly reactive aryl iodides, can be tolerated. The primary innovation lies in the use of a proton to terminate the ipso aryl intermediate and regenerate the active palladium catalyst. This unique mode of reactivity in the palladium/norbornene catalysis should open the door for developing new redox-neutral methods for site-selective arene functionalization.A redox-neutral ortho functionalization of aryl boroxines via palladium/norbornene cooperative catalysis is developed. The ortho amination and acylation are achieved with carboxylic acid anhydrides and O-benzoyl hydroxylamines as an electrophile, respectively, whereas protonation occurs at the ipso position. This transformation avoids using either extra oxidants and reductants or stoichiometric bases and acids. In addition, orthogonal chemoselectivity between aryl iodide and boroxine moieties is demonstrated for pathway divergence.

Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes

Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine-cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.

Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation

Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel-Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste.

Rhodium-catalyzed ortho acylation of aromatic carboxylic acids

New directions: The carboxylic acid functional group directs the ortho acylation of benzoic acids with carboxylic anhydrides in the presence of a rhodium catalyst (see scheme; cod=cyclo-1,5-octadiene). The acylation at the ortho position is complementary to the meta selectivity of Friedel-Crafts reactions. The resulting products can undergo protodecarboxylation to deliver an aryl ketone. Copyright

NHC-Pd(II)-Im (NHC=N-heterocyclic carbene, Im=1-methylimidazole) complex catalyzed coupling reaction of arylboronic acids with carboxylic acid anhydrides in water

A well-defined N-heterocyclic carbene (NHC)-palladium chloride-imidazole complex exhibited high catalytic activity in the coupling reaction of arylboronic acids with carboxylic acid anhydrides in pure water under mild conditions. Under the optimal conditions, all reactions gave the desired coupling products in moderate to high yields.

Palladium-phosphinous acid-catalyzed cross-coupling of aryl and acyl halides with aryl-, alkyl-, and vinylzinc reagents

(Chemical Equation Presented) Several palladium-phosphinous acids have been prepared and employed in cross-coupling reactions of aryl or acyl halides with aliphatic and aromatic organozinc reagents. The POPd7-catalyzed reaction of aryl halides, including electron-rich aryl chlorides, and arylzinc reagents was found to afford biaryls exhibiting alkoxy, alkylthio, amino, ketone, cyano, nitro, ester, and heteroaryl groups in 75-93% yield. Excellent results were obtained with sterically hindered substrates which gave di- and tri-ortho-substituted biaryls in up to 92% yield. Aryl halides also undergo POPd7-catalyzed aryl-vinyl and aryl-alkyl bond formation under mild conditions. Styrenes and alkylarenes were prepared in 79-93% yield from aryl halides and vinyl or alkylzinc reagents. The replacement of aryl halides by acyl halides provides access to ketones which were produced in up to 98% yield when POPd was used as catalyst. This approach overcomes the limited substrate scope, reduced regiocontrol, and low functional group tolerance of traditional Friedel-Crafts acylation methods.

Synthesis of substituted phenyl ketones via Pd-catalysed hydrodechlorination of their polychlorinated derivatives

The following compounds, 2- and 3-methylacetophenones, 2- and 3-methylbenzophenones, and 2,2'-, 2,3'- and 3,3'-dimethylbenzophenones have been synthesized through a Pd-catalysed hydrodechlorination of the corresponding dichlorinated derivatives. The reaction has been carried out under multiphase conditions at 30-50°C, by bubbling H2 at atmospheric pressure into a biphasic system constituted by an organic substrate solution (isooctane solvent) and an aqueous alkaline solution (50% aq KOH), in the presence of Pd/C (5% wt) and Aliquat 336 (tricaprylylmethylammonium chloride). Likewise, fluorinated aceto- and benzophenones (4-fluoro-3-methylacetophenone and 4-fluoro-3-methylbenzo-, 4-fluoro-2',3-dimethylbenzo-, 4-fluoro-3,3'-dimethylbenzophenones) have been prepared starting from the corresponding chlorinated methylfluoro and dimethyfluoro ketones. Under such conditions, the presence of the onium salt allows the reaction to proceed with a high chemoselectivity: chlorine is removed while both the reduction of the carbonyl group and/or fluorine removal are prevented.

Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-imidazolyl)alkyl]- 1(2H)-phthalazinones

A number of 4-substituted 2-[ω-(1-imidazolyl)alkyl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane A2 synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.

Reaction of Diazonium Salts with Transition Metals. Part 13. Palladium-catalyzed Carbonylative Coupling of Arenediazonium Salts with Organotin Reagents to give Aromatic Ketones

Palladium-catalyzed reactions of arenediazonium salts (ArN2X; Ar=Y-Ph, Y=H, 2-, 3-, 4-Me, 2-Ph, 2-, 3-MeO, 2-, 3-, 4-Cl, 4-Br, 4-I, 2-, 3-, and 4-NO2, X=BF4 and PF6) with carbon monoxide and organostannanes (R4Sn, R=Me, Et, and Ph; RSnMe3, R=Ph, 2-, 3-, 4-MeC6H4, and 4-ClC6H4; RSnEt3, R=4-NO2C6H4; RSnBu3, R=Ph) gave aromatic ketones (ArCOR) in good yields (40-95percent) at room temperature.