Home Cart Sign in  
Chemical Structure| 611-73-4 Chemical Structure| 611-73-4
Chemical Structure| 611-73-4

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

Phenylglyoxylic acid is a key building block in the field of chemical synthesis and is widely used to synthesize pharmaceutical intermediates or food additives.

Synonyms: Benzoylformic acid

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations      Show More

Huddleston, Morgan ;

Abstract: Electrocatalytic valorization of biomass-derived intermediate compounds to value-added products has emerged as a promising approach to mitigate carbon emissions. Capitalizing on renewable electricity as a green energy input for conducting paired electrocatalysis is a promising approach in the field of biorefining. Simultaneous oxidation and reduction of 5-hydroxymethylfurfural (HMF) yields high value products such as 2,5-formylfurancarboxylic acid (FFCA) and 2,5-bishydroxymethylfurfural (BHMF) with applications in the food industry, fuel additives, and pharmaceuticals. Simultaneous upgrading of biomass derived 5-hydroxymethylfurfural (HMF) at both the anode and cathode has been previously explored, however the challenge of tunable selectivity has not been overcome. Traditional electrochemical methods often suffer from energy inefficiencies due to the need for a second conversion at the counter electrode, which can produce non-value-added byproducts. Amino acids are a key example of highly valuable products derived from biomass oxidation followed by reductive amination. Pharmaceutical and food industries will benefit from an alternative strategy to produce amino acids that does not rely on inefficient fermentation processes. The use of renewable biomass resources as starting materials makes this proposed strategy more desirable. HMF can be proven to selectively yield 5-formyl-2-furancarboxylic acid (FFCA) under the same electrochemical conditions as HMF hydrogenation to 2,5-bishydroxymethylfuran (BHMF). With 4-acetamido TEMPO (ACT) as a homogeneous oxidation mediator and silver galvanically displaced copper foam (Ag/Cu) as the cathodic electrocatalyst, both electrochemical conversions can be observed in an H-type cell simultaneously. By employing pH 10 carbonate buffer as the optimized electrolyte, water proves to be an effective proton source for both conversion which demonstrates the extremely mild conditions. HMF anodic conversion of 94% leads to FFCA formation of 83% yield and simultaneous HMF cathodic conversion of 100% yields BHMF at 99%. HMF also oxidizes to 2,5-diformylfuran (DFF) with 75% yield and subsequent amination with ammonium hydroxide followed by reductive hydrogenation yields 2,5-(dimethylamino) furan (DMAF). This paired electrochemical approach for the selective oxidation of biomass-derived α-hydroxyl acids to α-keto acids, followed by electrochemical reductive amination yield amino acids as the final products. Glycine, Alanine, and Leucine were synthesized with N-hydroxyphthalimide (NHPI) as the oxidation mediator and NH3 as the nitrogen source to yields of 70, 80, and 90%. Phenylalanine required tetramethylpiperidine Noxyl (TEMPO) oxidation mediator with applying the same 2.7 V yielded 100%. Our paired electrolysis improves selectivity and doubles electron efficiency, with the flow electrolyzer demonstrating its potential for large-scale applications. The main challenge for widespread use of our proposed paired electrocatalytic method is the cost of industrial-scale small molecule production. Paired electrocatalysis offers an alternative by using both half-reactions in an electrochemical cell to produce value-added chemicals from biomass feedstocks. The operational principles and benefits of various cell configurations are compared, along with an analysis of electrocatalysts. Heterogeneous and bifunctional catalysts in paired electrocatalysis optimize energy and chemical use, eliminating the need for purification. The future will require further optimization to enhance the benefits of biomass valorization through paired electrocatalysis, while addressing challenges like cost of precursors, large-scale facility expenses, and widespread adoption of sustainably sourced energy.

Purchased from AmBeed: ; ; ; ; ; ; ;

Kaili Yan ; Morgan L. Huddleston ; Brett A. Gerdes ; Yujie Sun ;

Abstract: Electrochemical conversion of biomass-derived intermediate compounds to high-value products has emerged as a promising approach in the field of biorefinery. Biomass upgrading allows for the production of chemicals from non-fossil-based carbon sources and capitalization on electricity as a green energy input. Amino acids, as products of biomass upgrading, have received relatively little attention. Pharmaceutical and food industries will benefit from an alternative strategy for the production of amino acids that does not rely on inefficient fermentation processes. The use of renewable biomass resources as starting materials makes this proposed strategy more desirable. Herein, we report an electrochemical approach for the selective oxidation of biomass-derived α-hydroxyl acids to α-keto acids, followed by electrochemical reductive amination to yield amino acids as the final products. Such a strategy takes advantage of both reactions at the anode and cathode and produces amino acids under ambient conditions with high energy efficiency. A flow electrolyzer was also successfully employed for the conversion of α-hydroxyl acids to amino acids, highlighting its great potential for large-scale application.

Purchased from AmBeed: ; ; ; ; 56-40-6 ; 156-06-9 ; ; ; ; ; ; ; 828-01-3 ;

Alternative Products

Product Details of Phenylglyoxylic acid

CAS No. :611-73-4
Formula : C8H6O3
M.W : 150.13
SMILES Code : O=C(O)C(C1=CC=CC=C1)=O
Synonyms :
Benzoylformic acid
MDL No. :MFCD00002575
InChI Key :FAQJJMHZNSSFSM-UHFFFAOYSA-N
Pubchem ID :11915

Safety of Phenylglyoxylic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of Phenylglyoxylic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 611-73-4 ]

[ 611-73-4 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 32202-61-2 ]
  • [ 611-73-4 ]
  • [ 1046786-77-9 ]
  • 2
  • [ 2905-56-8 ]
  • [ 611-73-4 ]
  • [ 14377-63-0 ]
  • 4
  • [ 611-73-4 ]
  • [ 118994-89-1 ]
  • ethyl 2-benzoyloxazole-5-carboxylate [ No CAS ]
  • 5
  • [ 54977-92-3 ]
  • [ 611-73-4 ]
  • [ 1618080-55-9 ]
  • 6
  • [ 54977-92-3 ]
  • [ 611-73-4 ]
  • [ 1618080-47-9 ]
  • 7
  • [ 1267217-46-8 ]
  • [ 611-73-4 ]
  • [ 1602493-36-6 ]
  • 8
  • [ 611-73-4 ]
  • [ 73852-19-4 ]
  • [ 21221-93-2 ]
  • 9
  • [ 16112-21-3 ]
  • [ 611-73-4 ]
  • (2-(benzo[d]thiazol-2-yl)-5-methylphenyl)(phenyl)methanone [ No CAS ]
  • 10
  • [ 939-57-1 ]
  • [ 611-73-4 ]
  • [ 22966-01-4 ]
  • 12
  • [ 611-73-4 ]
  • [ 1575-37-7 ]
  • [ 1741-50-0 ]
  • 13
  • [ 150-13-0 ]
  • [ 611-73-4 ]
  • [ 582-80-9 ]
  • 14
  • [ 6563-13-9 ]
  • [ 611-73-4 ]
  • 8-benzoyl-6-methoxyquinoline 1-oxide [ No CAS ]
  • 15
  • [ 4139-61-1 ]
  • [ 611-73-4 ]
  • 8-bromo-3-[2-(5-bromo-2-hydroxyphenyl)-2-oxoethyl]-3-phenyl-2H-furo[3,2-c]chromene-2,4(3H)-dione [ No CAS ]
  • 16
  • [ 17408-16-1 ]
  • [ 611-73-4 ]
  • 1-(3-nitrophenyl)-1-oxopropan-2-yl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In ethyl acetate; at 80℃; for 24h;Sealed tube; General procedure: The mixture of phenylglyoxylic acid (0.2mmol), propiophenone (0.2mmol), TBHP (0.4mmol), TBAI (0.04mmol) and ethyl acetate (2mL) was stirred at 80C for 24h in a 15mL sealed tube successively. After cooling down, the reaction mixture was washed with Na2S2O3 solution, and extracted by ethyl acetate for three times. The obtained top organic layer was dried with anhydrous MgSO4. After drying, the mixture was concentrated under vacuum, and the crude product was purified by column chromatography on silica gel with petroleum ether-ethyl acetate (50:1) as eluent.
  • 17
  • [ 611-73-4 ]
  • [ 41394-05-2 ]
  • 18
  • [ 2905-56-8 ]
  • [ 611-73-4 ]
  • (1-benzyl-1,4,5,6-tetrahydropyridin-3-yl)(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With di-tert-butyl peroxide; copper(ll) bromide; In acetonitrile; at 60℃; under 760.051 Torr; for 24h; In the reaction tube is sequentially added 1n (0.5 mmol, 88 mg), 2a (0.6 mmol, 90 mg), acetonitrile (3 ml), copper bromide (0.05 mmol, 11 mg) and di-tert-butyl peroxide (1 mmol, 183 μl), in air (1 atm) atmosphere at 60 C stirring reaction 24 h. Then add 10 ml saturated salt water quenching reaction, extracted with ethyl acetate (10 ml × 3), combined with the organic phase, dried with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=5/1) to get the yellow solid product 3n (71 mg, 51%).
  • 19
  • [ 5430-45-5 ]
  • [ 611-73-4 ]
  • (5-chloroisoquinolin-1-yl)(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With ammonium peroxydisulfate; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; In dimethyl sulfoxide; at 20℃; for 12h;Inert atmosphere; Irradiation; Green chemistry; General procedure: Heterocycle (0.10mmol, 1 equiv)ammonium persulfate (0.20 mmol, 2equiv),[Ir{dF(CF3ppy)}2(dtbbpy)]PF6 ( 0.2 mol%),α-keto acids(1.0mmol10equiv)wereplaced in a dry glass tube.Then, anhydrous DMSO1mLwereinjected into the tubeby syringe under a N2 atmosphere.The solution was then stirred at roomtemperatureunder the irradiation of 15W blue LEDs strip for 12h.After completion of thereaction,then saturated Na2CO3solution was added to adjust pH to basic.Thecombined organic layer was washed with brine and then dried overanhydrousNa2SO4.The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum andethylacetate.
81% With ammonium peroxydisulfate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; In dimethyl sulfoxide; for 12h;Inert atmosphere; Irradiation; Add 33 mg of <strong>[5430-45-5]5-chloroisoquinoline</strong> to a 5 mL round bottom flask,60 mg of benzoylformic acid, 91 mg of (NH4)2S2O8 and 11 mg of Ir[dF(CF3)ppy]2(dtbbpy)(PF6),Add 2 mL of dried DMSO solvent with a syringe.The reaction vessel is closed and deaerated under nitrogen at a low temperature.The reaction vessel was placed under a blue LED lamp for 12 h,Water was added to the reaction system and extracted with dichloromethane.Combine the organic phase,After drying with anhydrous sodium sulfate,Filter and concentrate to obtain a crude product,Then using a mixed solution of petroleum ether/ethyl acetate as an eluent,Purified by silica gel column chromatography,5-Chloro-1-benzoylisoquinoline was obtained.
  • 20
  • [ 13220-33-2 ]
  • [ 611-73-4 ]
  • 1-methylpyrrolidin-3-yl 2-oxo-2-phenylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25℃;Inert atmosphere; To a stirred solution of N-methyl pyrrol i din- 3-ol (2, 1 equiv) and Et3N (1.2 equiv) in dichloromethane was added a solution of 2- oxo-2- phenyl acetyl chloride (1.1 equiv) in dichloromethane at 0 °C under nitrogen atmosphere for 15 min. The resulting solution was allowed to stir at room temperature over 12h. After completion, the mixture was quenched with water and extracted with diethyl ether to afford the pure product (3B). (0044) Similarly, the product 3B is also obtained by reaction of 2 with other reagents, phenyl oxalic acid, methyl phenyl oxalate, and phenyl hemi-oxaldehyde respectively as shown in Scheme 2.
  • 21
  • [ 114046-25-2 ]
  • [ 611-73-4 ]
  • 4-(1-((4-methoxyphenyl)amino)-2-keto-2-phenylethyl)benzonitrile [ No CAS ]
  • 22
  • [ 4596-92-3 ]
  • [ 611-73-4 ]
  • N-(4-chloro-2-formylphenyl)-2-oxo-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triphenylphosphine; copper(I) bromide; In 1,2-dichloro-ethane; at 110℃; for 12.0h;Schlenk technique; Inert atmosphere; The preparation method is:0.3 mmol of <strong>[4596-92-3]5-<strong>[4596-92-3]chlorobenzo[c]isoxazole</strong></strong> (46 mg), 0.6 mmol benzoylformic acid (90.1 mg), 0.015 mmol of copper bromide (3.3 mg) and 0.06 mmol of triphenylphosphine (15.7 mg) were added to a 25 ml schlenk tube under reduced pressure. The reaction tube was replaced with argon three times. 1,2-dichloroethane (3 ml) was added, and the mixture was stirred at 110 C for 12 hours. At the end of the reaction, 100-200 mesh column chromatography silica gel was added. The solvent was distilled off under reduced pressure, and the crude product was separated by silica gel column chromatography. And eluted with a mixture of petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 20:1). The TLC elution tracking test is used to collect the eluate containing the target product. Combining the target product eluates, evaporation and concentration gave the ortho-aldehyde group of the alpha-ketoamide compound of the formula III. This material was a yellow solid with a yield of 75%.
  • 23
  • [ 19012-02-3 ]
  • [ 611-73-4 ]
  • 1-(4-benzoyl-1-methyl-1H-indol-3-yl)ethanone [ No CAS ]
  • 24
  • [ 611-73-4 ]
  • [ 446065-11-8 ]
  • [ 4335-77-7 ]
  • 25
  • [ 13708-12-8 ]
  • [ 611-73-4 ]
  • C16H12N2O [ No CAS ]
  • C16H12N2O [ No CAS ]
  • 26
  • [ 72652-32-5 ]
  • [ 611-73-4 ]
  • 1-(5-benzoyl-4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one [ No CAS ]
  • 28
  • [ 29074-77-9 ]
  • [ 103-67-3 ]
  • [ 611-73-4 ]
  • N-benzyl-3-(3-ethylphenyl)-N-methyl-1-phenylprop-2-yn-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With Fe3O4(at)CuSiO3; In neat (no solvent); at 100.0℃; for 16.0h;Inert atmosphere; General procedure: A dried reaction tube equipped with a stir bar was loaded with α-keto acids (0.5 mmol), amine (0.65 mmol),alkyne (0.8 mmol), Fe3O4CuSiO3 (3 mg) under the atmosphere of Ar2 at a ceiling temperature of 90 C for 16 h. The resulting reaction mixture was loaded on a silica gel column and flashed with 4-10% ethyl acetate inpetroleum ether to afford the desired product.
 

Historical Records

Technical Information

Categories