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1074-12-0

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1074-12-0 Usage

Chemical Properties

white to light yellow powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 830, 1988 DOI: 10.1021/jo00239a027Tetrahedron Letters, 27, p. 5139, 1986 DOI: 10.1016/S0040-4039(00)85154-0

Enzyme inhibitor

This commercially available peptide/protein-modifying reagent (FW = 134.13 g/mol; CAS 1074-12-0), occasionally called benzoylformaldehyde, is a mild oxidant that reacts covalently with guanidinium groups at pH ~ 7, consuming two moles of reagent per mole of reactive arginyl residue. Modified guanidinium groups are relatively stable below pH 4; however, the original guanidinium group is slowly regenerated at neutral or alkaline pH. Upon prolonged incubation with phenylglyoxal, a-amino groups may also be modified. See also Glyoxal; 4-Hydroxyphenylglyoxal; etc. Target(s): To date, over 240 enzymes are inhibited by phenylglyoxal

Check Digit Verification of cas no

The CAS Registry Mumber 1074-12-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 4 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1074-12:
(6*1)+(5*0)+(4*7)+(3*4)+(2*1)+(1*2)=50
50 % 10 = 0
So 1074-12-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O2.H2O/c9-6-8(10)7-4-2-1-3-5-7;/h1-6H;1H2

1074-12-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name PHENYLGLYOXAL

1.2 Other means of identification

Product number -
Other names 2-Oxo-2-phenylacetaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1074-12-0 SDS

1074-12-0Related news

Mild gold-catalyzed aerobic dehydrogenative coupling of amines and PHENYLGLYOXAL (cas 1074-12-0) derivatives08/02/2019

A simple and efficient gold-catalyzed coupling of secondary amine with phenylglyoxal derivatives has been developed, which provides a practical synthetic strategy for the synthesis of substituted α-ketoamides under mild reaction conditions.detailed

1074-12-0Relevant articles and documents

Palladium/benzoquinone-catalyzed electrochemical oxidation of alcohols under anaerobic conditions

Amatore, Christian,Cammoun, Chama,Jutand, Anny

, p. 2173 - 2178 (2007)

Primary and secondary alcohols are oxidized to aldehydes and ketones, respectively, under anaerobic conditions in DMF at 80°C, in the presence of a base and catalytic amounts of Pd(OAc)2 and p-benzoquinone. The latter oxidizes the transient Pd(0) formed in the catalytic cycle to Pd(II) and p-hydroquinone is re-oxidized electrochemically. Georg Thieme Verlag Stuttgart.

Oxidation of active methylenes by dimethyl sulfoxide: A new ninhydrin synthesis

Schipper,Cinnamon,Rascher,Chiang,Oroshnik

, p. 6201 - 6204 (1968)

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Regioselective oxidative cross-coupling of benzo[d] imidazo[2,1- b] thiazoles with styrenes: A novel route to C3-dicarbonylation

Shaik, Siddiq Pasha,Sultana, Faria,Ravikumar,Sunkari, Satish,Alarifi, Abdullah,Kamal, Ahmed

, p. 7696 - 7704 (2017)

A novel I2 promoted, highly efficient metal-free and peroxide-free greener domino protocol for the C3-dicarbonylation of benzo[d]imidazo[2,1-b]thiazoles (IBTs) with styrenes has been developed via oxidative cleavage of the C(sp2)-H bond, followed by C3-nucleophilic attack of IBT and oxidation. Interestingly, under these conditions 2-(benzo[d]imidazo[2,1-b]thiazol-2-yl)aniline gave the benzo[4′,5′]thiazolo[2′,3′:2,3]imidazo[4,5-c]quinoline derivative via oxidative cleavage of the C(sp2)-H bond, followed by Pictet-Spengler cyclization and aromatization. This method offers the advantages of broad substrate scope, ecofriendly feature and high atom economy apart from higher yields.

Synthesis and solid-state luminescence of highly-substituted 6-amino-2H-pyran-2-one derivatives

Karpov, Sergey,Kayukov, Yakov,Grigor'ev, Arthur,Nasakin, Oleg,Kayukova, Olga,Tafeenko, Viktor

, (2020)

A fast and convenient synthesis and solid-state luminescence properties of new highly-substituted 6-amino-2H-pyran-2-one derivatives is described. These compounds were obtained from inexpensive and available 2-acyl(aroyl)-1,3-dicyano-1,3-bis-methoxycarbonylpropenides via regioselective heterocyclization under the action of sulfuric and hydroiodic acid. Compounds containing 6-amino-2H-pyran-2-one moiety are nearly unstudied, but are of interest for obtaining condensed biologically active compounds based on this scaffold.

Iodine-promoted five-component reaction using fragment assembly strategy to construct dihydrooxepines

Zhao, Peng,Wu, Xia,Geng, Xiao,Wang, Can,Wu, Yan-Dong,Wu, An-Xin

, p. 4323 - 4330 (2018)

An iodine-promoted fragment assembly strategy for the synthesis of fused heterocycles has been established. It provides an efficient route to construct pyrazolone-oxepine-pyrazoles from phenylhydrazines, aryl methyl ketones and acetoacetate esters. Notably, acetoacetate esters play two distinct pivotal roles in the five-component reaction by realizing the unique reactivities of methyl, methylene and carbonyl groups to construct 3-methyl-5-pyrazolone skeletons and by the reaction of methyl and carbonyl groups to form a C (sp3)-O bond.

Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones

Amador, Adrian G.,Sherbrook, Evan M.,Yoon, Tehshik P.

, p. 4722 - 4725 (2016)

Control of stereochemistry in photocycloaddition reactions remains a substantial challenge; almost all successful catalytic examples to date have involved [2 + 2] photocycloadditions of enones. We report a method for the asymmetric [3 + 2] photocycloaddition of aryl cyclopropyl ketones that enables the enantiocontrolled construction of densely substituted cyclopentane structures not synthetically accessible using other catalytic methods. These results show that the dual-catalyst strategy developed in our laboratory broadens synthetic chemists' access to classes of photochemical cycloadditions that have not previously been feasible in enantioselective form.

Employing Arylacetylene as a Diene Precursor and Dienophile: Synthesis of Quinoline via the Povarov Reaction

Yu, Xiao-Xiao,Zhao, Peng,Zhou, You,Huang, Chun,Wang, Li-Sheng,Wu, Yan-Dong,Wu, An-Xin

, p. 8381 - 8388 (2021)

A novel I2-mediated Povarov reaction of arylacetylenes and anilines for the synthesis of 2,4-substituted quinolines has been developed, in which arylacetylene first acts as both a diene precursor and dienophile. This work further develops the Povarov reaction to expand the types of diene precursors. Preliminary mechanistic studies indicate that the I2/DMSO system realized the oxidative carbonylation of C(sp)-H of arylacetylene and then undergoes a [4 + 2] cycloaddition reaction.

Iodine-Mediated Domino Protocol for the Synthesis of Benzamides from Ethylarenes via sp3 C-H Functionalization

Vadagaonkar, Kamlesh S.,Kalmode, Hanuman P.,Prakash, Sattey,Chaskar, Atul C.

, p. 1677 - 1682 (2015)

An efficient, metal-free domino protocol for the synthesis of benzamides has been developed from ethylarenes using aqueous ammonia. The reaction proceeds through the formation of triiodomethyl ketone intermediate in the presence of iodine as the promoter and TBHP as an oxidant followed by nucleophilic substitution with aqueous ammonia, forming an amide. This operationally simple, functional-group-tolerant tandem approach provides an easy access to the broad range of biologically important benzamides.

-

Bailey,Colomb

, p. 4238 (1957)

-

Au-Pd alloy cooperates with covalent triazine frameworks for the catalytic oxidative cleavage of β-O-4 linkages

Zhao, Li,Shi, Song,Zhu, Guozhi,Liu, Meng,Gao, Jin,Xu, Jie

, p. 6707 - 6716 (2019)

To design highly efficient catalysts for the cleavage of the C-O/C-C bond is the key task in the depolymerization of lignin. Bimetallic alloy catalysts Au-Pd-CTFs were developed to be effective in the oxidative cleavage of β-O-4 lignin model compounds with O2. Au-Pd nanoparticles with an Au/Pd molar ratio between 1?:?1 and 1?:?1.5 showed the highest cleavage efficiency. The kinetics of the reaction process revealed that a synergistic effect between Au and Pd played a crucial role in the oxidation of Cα-OH into CαO, which was the rate-determining step for the whole oxidative cleavage process. Further insight revealed that the cooperative effect between Au-Pd nanoparticles and the support covalent triazine frameworks (CTFs) facilitated the cleavage of the formed β-O-4 ketone compound to the corresponding aromatics. In addition, Au-Pd-CTF catalysts also showed efficiency in the oxidative transformation of the organosolv lignin. This catalytic system will provide guidance in the oxidative cleavage of β-O-4 linkages in lignin.

A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

Amador, Adrian G.,Sherbrook, Evan M.,Lu, Zhan,Yoon, Tehshik P.

, p. 539 - 547 (2018)

A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions o

-

Ramirez et al.

, p. 5763 (1960)

-

Synthesis of 2-acyl-benzo[1,3-d]selenazoles via domino oxidative cyclization of methyl ketones with bis(2-aminophenyl) diselenide

Balaguez, Renata A.,Betin, Eduardo S.,Barcellos, Thiago,Lenard?o, Eder J.,Alves, Diego,Schumacher, Ricardo F.

, p. 1483 - 1487 (2017)

A general, practical and simple one-pot synthesis of 2-acyl-benzo[1,3-d]selenazoles was developed by reacting a wide range of 2-arylethane-1,2-diones, generated in situ from commercially available aryl methyl ketones, with bis(2-aminophenyl) diselenide, promoted by Na2S2O5 in DMSO at 100 °C. Comparatively, the reactions were conducted under conventional heating and microwave irradiation. The use of focused microwave irradiation drastically decreased the reaction time from 48 to 2 h with a gain in the reaction yield for most cases. Still, 2-phenylacyl-benzo[1,3-d]selenazole was elected to react with sodium borohydride and butylmagnesium bromide, giving the respective secondary and tertiary alcohols under mild reaction conditions.

NaHS·n H2O-induced umpolung: The synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles

Geng, Xiao,Wu, Xia,Wang, Can,Zhao, Peng,Zhou, You,Sun, Xuan,Wang, Ling-Jiao,Guan, Wen-Juan,Wu, Yan-Dong,Wu, An-Xin

, p. 12730 - 12733 (2018)

An efficient method for constructing 2-acyl-3-aminoindoles from methyl ketones and 2-aminobenzonitriles is described, in which NaHS·nH2O is used as a novel umpolung reagent for the first time in organic synthesis. Mechanistic studies revealed that the key step involved an Eschenmoser sulfide contraction reaction.

Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines

Coogan, Niall T.,Chimes, Michael A.,Raftery, James,Mocilac, Pavle,Denecke, Melissa A.

, p. 8684 - 8693 (2015)

A new, regioselective synthesis of V-shaped 2,9-bis(6-(4-halophenyl)-1,2,4-triazin-3-yl)-1,10-phenanthrolines (4XPhBTPhen) ligands was developed, creating access to a simple and reliable synthesis of precursors for future supramolecular actinide complexing systems. Described is a reactant-directed regioselective synthetic method, which was found to be high yielding and reliable and yields exclusively 6,6′-phenyl BTPhen derivatives (including 4-chloro and 4-bromo) in five simple steps. Molecular and crystal structures of PhBTP and PhBTPhen products are fully determined and both were found to be in space group C2/c. Additionally, molecular and crystal structures of Z and E isomers of 2-hydrazono-2-phenylacetaldehyde oxime, a reagent in the synthetic route, reveal existence of strong intramolecular N-H?O hydrogen bonding in the Z isomer explaining its lower solubility in water.

Experimental and Theoretical Studies on Iron-Promoted Oxidative Annulation of Arylglyoxal with Alkyne: Unusual Addition and Migration on the Aryl Ring

Hung, Chen-Hsun,Gandeepan, Parthasarathy,Cheng, Lin-Chieh,Chen, Liang-Yu,Cheng, Mu-Jeng,Cheng, Chien-Hong

, p. 17015 - 17021 (2017)

An Fe(III)-promoted oxidative annulation reaction was developed for the synthesis of 1,2-naphthoquinones. A variety of substituted arylglyoxals and internal alkynes undergo the transformation in the presence of FeCl3 at room temperature to afford the 1,2-naphthoquinone products in good yields in a short reaction time. Interestingly, the products show unusual pseudomigration of the substituent on the arene ring of arylglyoxals. A possible mechanism involving Fe(III)-promoted formation of a vinyl cation from arylglyoxal and alkyne, electrophilic addition of the vinyl cation to the ipso carbon of the aryl group to give a spiral intermediate, and then migration of the keto carbon to the ortho carbon was proposed as key steps and verified using quantum mechanics.

Microwave-assisted green oxidation of alcohols with hydrogen peroxide catalyzed by iron complexes with nitrogen ligands

Cozzi, Irene Sofia,Crotti, Corrado,Farnetti, Erica

, p. 38 - 47 (2018)

Oxidation of primary and secondary alcohols, including two diols and glycerol, with H2O2 was catalyzed by the iron(II) complexes [FeL3](OTf)2 (L = 2,2′-bipyridine, 2,2′-bipyrimidine, 1,10-phenanthroline and substituted derivatives) and [FeL2](OTf)2 (L = bis(2-pyridinylmethyl)amine, 2,6-di(2-pyridyl)pyridine). The reactions were performed in acetonitrile, water or mixed solvent (typically water/acetonitrile 4:1) in a microwawe reactor at low power. Effect of addition of a cocatalyst, which in some cases improved the yields of the catalytic reaction, was investigated by means of NMR and UV–Visible techniques.

Boric acid-catalyzed synthesis of fused 1,2,4-triazine derivatives: a new class of red fluorescent organic compounds

Darehkordi, Ali,Salehi, Vahid,Rahmani, Fariba,Karimipour, Masoud

, p. 554 - 558 (2018)

[Figure not available: see fulltext.] Pyrido[1,2-b][1,2,4]triazines have been synthesized in good to excellent yields by condensation reaction between 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitriles and arylglyoxals in the presence of b

A direct phosphine-mediated synthesis of polyfunctionalized 1-aminopyrroles from arylglyoxals, phenylhydrazine and acetylene diesters

Poorand, Mahboobe Amirani,Anary-Abbasinejad, Mohammad,Darehkordi, Ali

, p. 141 - 147 (2017)

A new and efficient one-pot synthesis of 1-Aminopyrrole derivatives by three-component reaction of dialkyl acetylenedicarboxylates, phenylhydrazine and arylglyoxals in the presence of triphenylphosphine is described. The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded good yields of products.

Visible-Light-Driven Z -Selective Reaction of Methyl Ketones with DMSO: A Mild Synthetic Approach to Methylthio-Substituted 1,4-Enedione Promoted by Selectfluor

Rastogi, Gaurav K.,Deb, Mohit L.,Baruah, Pranjal K.

, p. 1095 - 1102 (2021)

Here we disclose a simple, visible-light-driven Z -selective synthesis of methylthio-substituted 1,4-enedione in a single step promoted by Selectfluor. Dimethyl sulfoxide is used as both the 'thio' source and the solvent. Molecular iodine and potassium persulfate are used as catalyst and oxidant, respectively. White light (CFL-30W) is used as the light source. The proposed mechanism involves a Kornblum reaction followed by aldol reaction.

Iodine-catalyzed tandem oxidative coupling reaction: A one-pot strategy for the synthesis of new coumarin-fused pyrroles

Yahyavi, Hoda,Heravi, Majid M.,Mahdavi, Mohammad,Foroumadi, Alireza

, p. 94 - 98 (2018)

The simple and facile strategy for the synthesis of 2,3-disubstituted-chromeno[4,3-b]pyrrole-4(1H)-ones has been established. This method describes the Kornblum oxidation reaction of acetophenones, followed by the Knoevenagle treatment of the resulted (he

Oda,Hayashi

, p. 2181 (1967)

I2/PhI(OAc)2 Copromoted Amination Reaction: Synthesis of α-Dicarbonylsulfoximine Derivatives by Incorporating an Intact Dimethyl Sulfoxide

Zhao, Peng,Wu, Xia,Geng, Xiao,Wang, Can,Zhou, You,Wu, Yan-Dong,Wu, An-Xin

, p. 8322 - 8329 (2019)

An I2/PhI(OAc)2 copromoted strategy using dimethyl sulfoxide as an "S/C2/O" source for preparing α-dicarbonylsulfoximine derivatives is reported. This process involves oxidative coupling to construct a C-N bond and electrophilic amin

Direct Synthesis of 2,3-Diaroyl Quinolines and Pyridazino[4,5- b]quinolines via an I2-Promoted One-Pot Multicomponent Reaction

Zhao, Peng,Wu, Xia,Zhou, You,Geng, Xiao,Wang, Can,Wu, Yan-Dong,Wu, An-Xin

, p. 2708 - 2711 (2019)

The first synthesis of 2,3-diaroyl quinolines via a formal [3 + 2 + 1] cycloaddition of enaminones, aryl methyl ketones, and aryl amines is disclosed. This reaction efficiently affords a 1,4-dicarbonyl scaffold, which is a useful building block for constructing complex fused heterocycles. Furthermore, the 1,4-dicarbonyl scaffold has been used directly to prepare pyridazino[4,5-b]quinoline skeletons in one-pot.

-

Kornblum et al.

, p. 6562 (1957)

-

Functionalized-1,3,4-oxadiazole ligands for the ruthenium-catalyzed Lemieux-Johnson type oxidation of olefins and alkynes in water

Hkiri, Shaima,Touil, Soufiane,Samarat, Ali,Sémeril, David

, (2021/11/30)

Three arene-ruthenium(II) complexes bearing alkyloxy(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl)methyl ligands were quantitatively obtained through the reaction of (E)-1-(4-trifluoromethylphenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-methanimine with the ruthenium precursor [RuCl2(η6-p-cymene)]2 in a mixture of the corresponding alcohol and CH2Cl2 at 50 °C. The obtained complexes were fully characterized by elemental analysis, infrared, NMR and mass spectrometry. Solid-state structures confirmed the coordination of the 1,3,4-oxadiazole moiety to the ruthenium center via their electronically enriched nitrogen atom at position 3 in the aromatic ring. These complexes were evaluated as precatalysts in the Lemieux-Johnson type oxidative cleavage of olefins and alkynes in water at room temperature with NaIO4 as oxidizing agent. Good to full conversions of olefins into the corresponding aldehydes were measured, but low catalytic activity was observed in the case of alkynes. In order to get more insight into the mechanism, three analogue arene-ruthenium complexes were synthesized and tested in the oxidative cleavage of styrene. The latter tests clearly demonstrated the importance of the hemilabile alkyloxy groups, which may form more stable (N,O)-chelate intermediates and increase the efficiency of the cis-dioxo-ruthenium(VI) catalyst.

Electrochemical oxidative synthesis of 2-benzoylquinazolin-4(3: H)-one via C(sp3)-H amination under metal-free conditions

Hu, Yongzhi,Ma, Xinhua,Hou, Huiqing,Sun, Weiming,Tu, Shuqing,Wu, Mei,Lin, Rongkun,Xu, Xiuzhi,Ke, Fang

, p. 6374 - 6379 (2021/10/12)

An electrochemically induced C(sp3)-H amination of 2-aminobenzamides with ketones using TBAI as a catalyst was developed, and provided 2-benzoylquinazolin-4(3H)-ones under metal-free conditions. The reaction proceeded using the relatively low-toxicity methanol as the solvent, employed molecular oxygen as the ideal green oxidant in a simple undivided cell, and exhibited high atom economy. The mechanism of this C(sp3)-H amination strategy was concluded to involve generation of an acetophenone radical, and its easy further oxidation to form 2-oxo-2-phenylacetaldehyde.

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