611-73-4 Usage
Description
Benzoylformic acid, also known as phenylglyoxylic acid, is a 2-oxo monocarboxylic acid derived from glyoxylic acid, where the aldehyde hydrogen is substituted by a phenyl group. It is characterized by its white to light yellow adhering crystal form and is widely utilized in various organic synthesis processes.
Uses
Used in Organic Synthesis:
Benzoylformic acid is used as a precursor in the synthesis of various compounds for different applications. It serves as a key intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
Benzoylformic acid is used as a building block for the synthesis of O-acyl acetanilides through decarboxylative o-acylation of acetanilides using a Pd catalyst. This process is essential in the development of new drugs and pharmaceutical compounds.
Used in Chemical Research:
In the field of chemical research, benzoylformic acid is employed in the synthesis of phenylhydroxycarbene by high-vacuum flash pyrolysis. Benzoylformic acid has potential applications in various chemical reactions and processes.
Used in Material Science:
Benzoylformic acid is used in the synthesis of 2-arylbenzothiazoles by reacting with o-aminothiophenol using ammonium niobium oxalate (ANO) as a catalyst. These compounds have potential applications in the development of new materials with specific properties.
Used in Diverse Applications:
Benzoylformic acid is also used in the synthesis of 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones by treating with o-aminophenol in the presence of an ammonium niobium oxalate catalyst. Additionally, it is employed in the synthesis of 2-aryl benzothiazoles through potassium persulfate (K2S2O8)-mediated oxidative condensation of benzothiazoles, which can be used in various industrial applications.
Synthesis Reference(s)
Journal of Medicinal Chemistry, 26, p. 1631, 1983 DOI: 10.1021/jm00365a015Organic Syntheses, Coll. Vol. 1, p. 241, 1941Tetrahedron Letters, 17, p. 3735, 1976 DOI: 10.1016/S0040-4039(00)93096-X
Synthesis
The synthesis of Benzoylformic acid is as follows:Acetophenone (120 g, 1 mol) was dissolved in 2000 ml of pyridine, and 165 g (1.5 mol) of selenium dioxide was added under stirring.The mixture was refluxed for 3 hours and left to cool overnight.Filter through celite, wash the filter cake with xylene, and combine the filtrate and washings with azeotropic evaporation.The evaporated residue was dissolved in 1 L of ethyl acetate and washed with 300 ml of 10% dilute hydrochloric acid.The organic layer was washed with 400 ml of 5% sodium hydroxide solution, and the washed aqueous layer was adjusted to pH 2-3 with 10% dilute hydrochloric acid.A white solid precipitates, is filtered, the filter cake is washed with water, and dried to obtain 120 g of a white solid.Yield: 87%, purity: 99.2%.
Purification Methods
If the sample is oily, then it may contain H2O. In this case dry it in a vacuum desiccator over P2O5 or KOH until crisp. For further purification dissolve 5.5g in hot CCl4 (750mL), add charcoal (2g, this is necessary otherwise the acid may separate as an oil), filter, cool in ice-water until crystallisation is complete. Filter the acid off, and the solvent on the crystals is removed by keeping the acid (4.5g) in a vacuum desiccator for 2 days. Slightly yellow crystals are obtained. It can be recrystallised also from *C6H6/pet ether, and can be distilled in a vacuum. The acid is estimated by titration with standard NaOH. The phenylhydrazone is recrystallised from EtOH, m 163-164o, and the semicarbazone acid has m 259o(dec) (from EtOH). The methyl ester distils at 137o/14mm, 110-111o/2mm, n 20 1.5850. [Baert & Kates J Am Chem Soc 67 1482 1945, Schaffer & Corey J Org Chem 24 1825 1959, Beilstein 10 H 654, 10 IV 2737.]
Check Digit Verification of cas no
The CAS Registry Mumber 611-73-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 1 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 611-73:
(5*6)+(4*1)+(3*1)+(2*7)+(1*3)=54
54 % 10 = 4
So 611-73-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
611-73-4Relevant articles and documents
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Banholzer,Schmid
, p. 548,553 (1956)
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Biosynthesis of Phenylglyoxylic Acid by LhDMDH, a Novel d -Mandelate Dehydrogenase with High Catalytic Activity
Tang, Cun-Duo,Shi, Hong-Ling,Xu, Jian-He,Jiao, Zhu-Jin,Liu, Fei,Ding, Peng-Ju,Shi, Hong-Fei,Yao, Lun-Guang,Kan, Yun-Chao
, p. 2805 - 2811 (2018)
d-Mandelate dehydrogenase (DMDH) has the potential to convert d-mandelic acid to phenylglyoxylic acid (PGA), which is a key building block in the field of chemical synthesis and is widely used to synthesize pharmaceutical intermediates or food additives.
One-Pot Synthesis of Phenylglyoxylic Acid from Racemic Mandelic Acids via Cascade Biocatalysis
Tang, Cun-Duo,Ding, Peng-Ju,Shi, Hong-Ling,Jia, Yuan-Yuan,Zhou, Mao-Zhi,Yu, Hui-Lei,Xu, Jian-He,Yao, Lun-Guang,Kan, Yun-Chao
, p. 2946 - 2953 (2019)
Phenylglyoxylic acid (PGA) are key building blocks and widely used to synthesize pharmaceutical intermediates or food additives. However, the existing synthetic methods for PGA generally involve toxic cyanide and complex processes. To explore an alternati
Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives
Ece, Hamdiye,Tange, Yuji,Yurino, Taiga,Ohkuma, Takeshi
supporting information, p. 935 - 939 (2021/02/22)
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.
Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives
Sun, Bin,Shi, Rongcheng,Zhang, Kesheng,Tang, Xiaoli,Shi, Xiayue,Xu, Jiayun,Yang, Jin,Jin, Can
supporting information, p. 6050 - 6053 (2021/06/21)
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.
Novel peptidomimetic peptide deformylase (PDF) inhibitors of Mycobacterium tuberculosis
Gokhale, Kunal M.,Telvekar, Vikas N.
, p. 148 - 156 (2020/08/26)
Emergence of MDR-TB and XDR-TB led to the failure of available anti-tubercular drugs. In order to explore, identify and develop new anti-tubercular drugs, novel peptidomimetic series of Mtb–peptide deformylase (PDF) inhibitors was designed and synthesized. In vitro antimycobacterial potential of compounds was established by screening of compounds against Mycobacterium tuberculosis H37Rv strain using MABA. Among them, ester series of compounds 4a, 4b, 4c, 4d, and 4e were found most active, with compound 4c being highly active and exhibiting minimum inhibitory concentration of 6.25?μg/ml against M.?tb H37Rv strain. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on Mtb-peptide deformylase (PDF), which is involved in the mycobacterium protein synthesis.