92965-01-0

Basic information

• Product Name: Benzoic acid, 2-(oxophenylacetyl)-, methyl ester
• Synonyms: methyl benzil-2-carboxylate
• CAS NO: 92965-01-0
• Molecular Formula: C16H12O4
• Molecular Weight: 268.269
• Mol File: 92965-01-0.mol

Chemical Properties

• Melting Point: 116-117 °C
• Boiling Point: 433.9±28.0 °C(Predicted)
• Density: 1.229±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzoic acid, 2-(oxophenylacetyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-(oxophenylacetyl)-, methyl ester(92965-01-0)
• EPA Substance Registry System: Benzoic acid, 2-(oxophenylacetyl)-, methyl ester(92965-01-0)

Safety Data

• Hazardous Substances Data: 92965-01-0(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 3839-29-0 α,α'-dioxo-bibenzyl-2-carboxylic acid 
• 74-88-4 methyl iodide 
• 2136-67-6 3-methoxy-2-phenyl-2-inden-1-one 
• 83-12-5 phenindione 
• 33578-05-1 methyl 2-(phenylethynyl)benzoate 

Downstream Products

• 67-56-1 methanol 
• 1452219-87-2 3-(4-methoxyphenyl)-3-phenylisochroman-1,4-dione 
• 1452219-86-1 3-(4-chlorophenyl)-3-phenylisochroman-1,4-dione 
• 1452219-90-7 3-(naphthalen-1-yl)-3-phenylisochroman-1,4-dione 
• 1452219-91-8 3-(naphthalen-2-yl)-3-phenylisochroman-1,4-dione 
• 1452219-94-1 3-([1,1'-biphenyl]-4-yl)-3-phenylisochroman-1,4-dione 
• 1452219-93-0 3-(4-(tert-butyl)phenyl)-3-phenylisochroman-1,4-dione 
• 1452219-88-3 3-(3-methoxyphenyl)-3-phenylisochroman-1,4-dione 
• 1452219-89-4 3-(2-methoxyphenyl)-3-phenylisochroman-1,4-dione 
• 1452219-92-9 3-(4-bromophenyl)-3-phenylisochroman-1,4-dione 
• 1452219-98-5 (E)-3-phenyl-3-styrylisochroman-1,4-dione 
• 22115-39-5 2-Carboxy-benzil 

Relevant articles and documents

(Ar-tpy)RuII(ACN)3: A Water-Soluble Catalyst for Aldehyde Amidation, Olefin Oxo-Scissoring, and Alkyne Oxygenation

The synthetic chemists always look for developing new catalysts, sustainable catalysis, and their applications in various organic transformations. Herein, we report a new class of water-soluble complexes, (Ar-tpy)RuII(ACN)3, utilizing designed terpyridines possessing electron-donating and -withdrawing aromatic residues for tuning the catalytic activity of the Ru(II) complex. These complexes displayed excellent catalytic activity for several oxidative organic transformations including late-stage C-H functionalization of aldehydes with NH2OR to valuable primary amides in nonconventional aqueous media with excellent yield. Its diverse catalytic power was established for direct oxo-scissoring of a wide range of alkenes to furnish aldehydes and/or ketones in high yield using a low catalyst loading in the water. Its smart catalytic activity under mild conditions was validated for dioxygenation of alkynes to highly demanding labile synthons, 1,2-diketones, and/or acids. This general and sustainable catalysis was successfully employed on sugar-based substrates to obtain the chiral amides, aldehydes, and labile 1,2-diketones. The catalyst is recovered and reused with a moderate turnover. The proposed mechanistic pathway is supported by isolation of the intermediates and their characterization. This multifaceted sustainable catalysis is a unique tool, especially for late-stage functionalization, to furnish the targeted compounds through frequently used amidation and oxygenation processes in the academia and industry.

Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions

We report an electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones. A variety of functional groups and heterocycle-containing substrates can be tolerated well under mild conditions.

Generation of 4-iodoisocoumarins through a TBAI-mediated oxidative cyclization of 2-alkynoates

A tetra-butylammonium iodide (TBAI)-mediated oxidative iodocyclization of 2-alkynoates for the synthesis of various 4-iodoisocoumarin is described herein, and the reaction is highly efficient and shows broad functional group tolerance. This newly develope

Synthesis of benzil-o-carboxylate derivatives and isocoumarins through neighboring ester-participating bromocyclizations of o-alkynylbenzoates

Bromide mediated neighboring ester-participating bromocyclizations of o-alkynylbenzoates are described here for the synthesis of benzil-o-carboxylates. 4-bromoisocoumarins are also synthesized when phenyl o-alkynylbenzoate is used as the substrate. Mechanistic studies suggest that the whole process is composed of an electrophilic bromocyclization and a dibromohydration-based ring-opening, and the neighboring ester group participates in the bromocyclization. Interestingly, the two oxygen atoms of the keto carbonyls in benzil-o-carboxylates are both derived from water. The electrophilic bromo source is in situ generated from the oxidation of bromide.

Method for synthesizing ph-dicarbonyl-aryl-formic-ether series compounds based on metal-free participation method

The invention discloses a method for synthesizing ph-dicarbonyl-aryl-formic-ether series compounds based on the metal-free participation method, and belongs to the technical field of organic chemistry. The method includes the steps that phalkynyl benzoic ether is used as a reaction substrate, bromide is added to serve as a bromine source, peroxosulfuric acid inorganic salt serves as an oxidizing agent, a solvent is added, the mixture is reacted for 6 hours to 12 hours at the temperature of 60 DEG C to 80 DEG C, then column chromatography silica gel (SiO2) is added, then the mixture continues to be stirred for 0.5 hour to 1 hour, filtering, extracting and drying are carried out, filtering is carried out again, filtering liquid is subjected to pressure reduction distillation, an organic solvent is removed, then rapid column chromatography is carried out, and the ph-dicarbonyl-aryl-formic-ether series compounds are obtained. By means of a reaction, using of a metal catalyst is avoided, the reaction condition is mild, the substrate is wide in applicability, easy and convenient to operate, low in cost, small in by product, high in product purity, convenient to separate and purify and capable of suiting for large-scale preparing.

Based on TBAB and Oxone synthesis of O - dicarbonyl aryl aldehyde or ketone series of compounds method (by machine translation)

The invention discloses based on TBAB and Oxone synthesis of O - dicarbonyl aryl aldehyde or ketone series of compounds method, organic chemical technical field, the method adopts the neighbouring alkyne basebenzyl aldehyde/ketone as a reaction substrate, adding brominated salt as a bromine source and the acidic inorganic salt as the oxidizing agent, adding solvent, at a temperature of 60 - 80 °C conditions, reaction 6 - 12 hours and adding the column chromatography silica gel (SiO2 ) Continue after the stirring 0.5 - 1 hours, filtration, extraction, drying, again after filtering the filtrate is distilled under reduced pressure to remove the organic solvent to rapid column chromatography to obtain the O - dicarbonyl aryl residue aldehyde, alkone series compound. The reaction prevents the metal catalytic use and complicated post-processing operation process, mild reaction conditions, the substrate has wide applicability, the operation is simple, low cost, few by-products, the product has high purity, facilitates separation of the purification, can be suitable for the preparation of a larger scale. (by machine translation)

NBS-Mediated Oxygen Transfer Reaction of Carbonyl in Ester: Efficient Synthesis of Benzil–o-carboxylate Derivative From o-Alkynylbenzoate

A neighbouring ester group-participated diketonization of o-alkynylbenzoate is described here for the synthesis of benzil-o-carboxylate. Application of the resulting benzil-o-carboxylate in the synthesis of quinoxalines is also reached from o-alkynylbenzoate in an one-pot fashion. This diketonization proceeds smoothly with a high regioselectivity under mild conditions. Importantly, neighbouring group plays an important role in diketonization. A plausible mechanism suggests that a bromo-incoporated isocoumarin cation is described as an intermediate, and the whole process is constituted by NBS-mediated electrophilic 6-endo annulation and oxygen transfer reaction through NBS-mediated oxidative ring-opening. Water serves as a nucleophile of ring-opening. (Figure presented.).

One-pot synthesis of 2-(quinoxalin-2-yl)benzoate through NBS-mediated sequential reaction of 2-alkynylbenozate and aryl-1,2-diamine

A metal-free route involving a sequential reaction of 2-alknylbenzoate and aryl-1,2-diamine is described for the generation of 2-(quinoxalin-2-yl)benzoate. The sequential reaction combines NBS-mediated diketonization of 2-alknylbenzoate and condensation reaction with aryl-1,2-diamine, and proceeds smoothly under mild reaction conditions and an array of 2-(quinoxalin-2-yl)benzoate is achieved with high efficiency and excellent functional group tolerance. Mechanism studies indicate oxygen transfer reaction is observed and water is incorporated into neighboring ester group.

Synthesis of α-diketones from alkylaryl- and diarylalkynes using mercuric salts

Both alkylarylalkynes and diarylalkynes 1 are converted into the α-diketones 2 in good yield by the use of mercuric salts, e.g., mercuric nitrate hydrate or mercuric triflate, in the presence of water. Other mercuric salts, e.g., sulfate, chloride, acetate, or trifluoroacetate, do not provide the diketone product. A possible mechanism is proposed.

Gold(I)-catalyzed diketonization of alkynes and its application for the one-pot synthesis of quinoxaline derivatives

A gold(I)-catalyzed oxidative diketonization of alkynes by water in the presence of Selectfluor has been achieved. The application of the present protocol for the one-pot synthesis of quin-oxaline derivatives from alkynes and o-phenylenediamines has also been successful. Georg Thieme Verlag Stuttgart · New York.