7163-50-0

Basic information

• Product Name: 4-methylbenzoylformic acid
• Synonyms: Benzeneacetic acid, 4-methyl-alpha-oxo-;Para-methylbenzoylformic acid;2-Oxo-2-(p-tolyl)acetic acid;Benzeneacetic acid,4-Methyl-a-oxo-;(4-Methylphenyl)glyoxylic acid
• CAS NO: 7163-50-0
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.158
• Mol File: 7163-50-0.mol

Chemical Properties

• Boiling Point: 290.6 °C at 760 mmHg
• Flash Point: 143.8 °C
• Appearance: /
• Density: 1.244 g/cm³
• Vapor Pressure: 0.000945mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: 2-8°C
• PKA: 2.22±0.54(Predicted)
• CAS DataBase Reference: 4-methylbenzoylformic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylbenzoylformic acid(7163-50-0)
• EPA Substance Registry System: 4-methylbenzoylformic acid(7163-50-0)

Safety Data

• Hazardous Substances Data: 7163-50-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-methylbenzoylformic acid is used as a building block for the synthesis of various pharmaceuticals due to its versatile chemical structure and reactivity.
Used in Agrochemical Industry:
4-methylbenzoylformic acid is used as a precursor in the production of agrochemicals, contributing to the development of effective pest control agents.
Used in Medical Treatment:
4-methylbenzoylformic acid is used as a potential therapeutic agent for certain medical conditions, leveraging its anti-inflammatory and analgesic properties to alleviate symptoms and improve patient outcomes.

InChI:InChI=1/C9H8O3/c1-6-2-4-7(5-3-6)8(10)9(11)12/h2-5H,1H3,(H,11,12)

Upstream product

• 102096-74-2 1,3-diphenyl-5-p-tolyl-pent-2-ene-1,5-dione 
• 122-00-9 para-methylacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 
• 201230-82-2 carbon monoxide 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 4974-59-8 2,2-dichloro-4'-methylacetophenone 
• 14271-73-9 4-methylbenzoyl cyanide 
• 18584-20-8 4-methylmandelic acid 
• 130749-20-1 2,2,2-Tris-benzotriazol-1-yl-1-p-tolyl-ethanone 
• 75716-86-8 α-(4-methylphenyl)-α-oxoacetic acid tert-butyl ester 
• 4755-77-5 Ethyl oxalyl chloride 
• 108-88-3 toluene 

Downstream Products

• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 
• 86604-95-7 2,3-Dihydro-6-(4-methyl-phenyl)-5H-thiazolo<2,3-c><1,2,4>-triazin-5-on 
• 622-47-9 4-tolylacetic acid 
• 18584-20-8 4-methylmandelic acid 
• 100-21-0 terephthalic acid 
• 99-94-5 p-Toluic acid 
• 1427669-82-6 (1-(pyrimidin-2-yl)-1H-indol-2-yl)(p-tolyl)methanone 
• 51579-89-6 N,N‐dimethyl‐2‐oxo‐2‐(p‐tolyl)acetamide 
• 1486470-32-9 N-(3-t-butyl-1-phenyl-1H-pyrazol-5-yl)-2-oxo-2-p-tolylacetamide 
• 1486470-39-6 N-(3-t-butyl-1-m-tolyl-1H-pyrazol-5-yl)-2-oxo-2-p-tolylacetamide 
• 1486470-36-3 N-[3-t-butyl-1-(3-nitrophenyl)-1H-pyrazol-5-yl]-2-oxo-2-p-tolylacetamide 
• 3837-95-4 (E)-1-(4-methylphenyl)-2-buten-1-one 
• 1476804-80-4 C₂₃H₁₈N₂O₂ 
• 1476803-97-0 C₂₃H₂₀N₂O₃ 

Relevant articles and documents

Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives

3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.

Rapid assembly of α-ketoamides through a decarboxylative strategy of isocyanates with α-oxocarboxylic acids under mild conditions

A simple and practical method for α-ketoamide synthesis via a decarboxylative strategy of isocyanates with α-oxocarboxylic acids is described. The reaction proceeds at room temperature under mild conditions without an oxidant or an additive, showing good substrate scope and functional compatibility. Moreover, the applicability of this method was further demonstrated by the synthesis of various bioactive molecules and different application examples through a two-step one-pot operation.

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives

A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.

Hypervalent Iodine(III)-Promoted Radical Oxidative C-H Annulation of Arylamines with α-Keto Acids

A novel catalyst-free radical oxidative C-H annulation reaction of arylamines with α-keto acids toward benzoxazin-2-ones synthesis under mild conditions was developed. This hypervalent iodine(III)-promoted process eliminated the use of a metal catalyst or additive with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a radical initiator for this reaction. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A.

Possible competitive modes of decarboxylation in the annulation reactions ofortho-substituted anilines and arylglyoxylates

Annulation reactions ofortho-substituted anilines and arylglyoxylates in the presence of K2S2O8at 80 °C under metal-free neutral conditions have been investigated, which extended a platform for the tandem synthesis of nitrogen heterocycles. While arylglyoxylic acids are known to undergo decarboxylation to form an acyl radical in the presence of K2S2O8and used in the Minisci acylation of electron-deficient (hetero)aromatics, their reactions with electron-richortho-substituted anilines to form nitrogen heterocycles have recently been studied. Depending upon the experimental conditions used in the reactions, the mechanism of the formation of heterocycles involving reactions of an acyl radical or aryl iminocarboxylic acids has been postulated. Given the subtle understanding of the mechanisms of annulation reactions of 2-substituted anilines and arylglyoxylates in the presence of K2S2O8, an extensive mechanistic investigation was undertaken. In the current study, the various mechanistic pathways including the generation of acyl, imidoyl, aminal, and N,O-hemiketal radicals have been postulated based on different possible decarboxylation modes. Some of the proposed intermediates are supported based on the available analytical data. The protocol uses a single, inexpensive reagent K2S2O8, which offers not only transition-metal-free conditions but also serves as the reagent for the key decarboxylation step. Taken together, this study complements the current development of the annulation reactions of 2-substituted anilines and arylglyoxylates in terms of synthesis and mechanistic understanding.

Direct 1,2-Dicarbonylation of Alkenes towards 1,4-Diketones via Photocatalysis

1,4-Dicarbonyl compounds are intriguing motifs and versatile precursors in numerous pharmaceutical molecules and bioactive natural compounds. Direct incorporation of two carbonyl groups into a double bond at both ends is straightforward, but also challenging. Represented herein is the first example of 1,2-dicarbonylation of alkenes by photocatalysis. Key to success is that N(n-Bu)4+ not only associates with the alkyl anion to avoid protonation, but also activates the α-keto acid to undergo electrophilic addition. The α-keto acid is employed both for acyl generation and electrophilic addition. By tuning the reductive and electrophilic ability of the acyl precursor, unsymmetric 1,4-dicarbonylation is achieved for the first time. This metal-free, redox-neutral and regioselective 1,2-dicarbonylation of alkenes is executed by a photocatalyst for versatile substrates under extremely mild conditions and shows great potential in biomolecular and drug molecular derivatization.

Visible-Light-Promoted Switchable Synthesis of C-3-Functionalized Quinoxalin-2(1H)-ones

A visible-light-promoted synthesis of quinoxalin-2(1H)-ones has been developed using 9-mesityl-10-methylacridinium perchlorate as an organo-photocatalyst. The atmosphere-controlled method (Ar/air) enabled the selective synthesis of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones under mild reaction conditions without the use of any metal catalysts or toxic reagents. A fluorescent labelling experiment showed that hydroxyl-containing quinoxalin-2(1H)-ones may have utility in various biological applications as potent fluorophores. (Figure presented.).

K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins

The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.

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Diazotrifluoroethyl Radical: A CF3-Containing Building Block in [3 + 2] Cycloaddition

We present herein a visible-light-induced [3 + 2] cycloaddition of a hypervalent iodine(III) reagent with α-ketoacids for the construction of 5-CF3-1,3,4-oxadiazoles that are of importance in medicinal chemistry. The reaction proceeds smoothly without a photocatalyst, metal, or additive under mild conditions. Different from the well-established trifluorodiazoethane (CF3CHN2), the diazotrifluoroethyl radical [CF3C(·)N2], a trifluoroethylcarbyne (CF3C?:) equivalent and an unusual CF3-containing building block, is involved in the present reaction system.