Phenylglyoxal

Base Information

• Chemical Name: Phenylglyoxal
• CAS No.: 1074-12-0
• Molecular Formula: C8H6O2
• Molecular Weight: 134.134
• Hs Code.: 29122900
• European Community (EC) Number: 214-036-1
• NSC Number: 627436,156299,26909
• UNII: N45G3015PA
• DSSTox Substance ID: DTXSID8025888
• Nikkaji Number: J95.649J,J919.790G
• Wikipedia: Phenylglyoxal
• Wikidata: Q5934181
• Metabolomics Workbench ID: 128282
• ChEMBL ID: CHEMBL233632
• Mol file: 1074-12-0.mol

Synonyms:Phenylglyoxal

Chemical Property of Phenylglyoxal

Chemical Property:

• Appearance/Colour: White to light yellow powder
• Vapor Pressure: 0.000795mmHg at 25°C
• Melting Point: ~76 °C
• Boiling Point: 199.8 °C at 760 mmHg
• Flash Point: 69.8 °C
• PSA: 34.14000
• Density: 1.133 g/cm³
• LogP: 1.06820
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 134.036779430
• Heavy Atom Count: 10
• Complexity: 134

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Oxo-2-phenylacetaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-41
• Safety Statements: 22-26-36-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C=O

Technology Process of Phenylglyoxal

There total 119 articles about Phenylglyoxal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 25.0%

benzalacetophenone (94-41-7) → phenylglyoxal hydrate (1074-12-0) + benzaldehyde (100-52-7)

Guidance literature:

With dihydrogen peroxide; In water; acetonitrile; at 20 ℃; for 5h; under 760.051 Torr;

DOI:10.1007/s10562-011-0668-1

Reference yield: 14.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + phenylacetylene (536-74-3) → phenylglyoxal hydrate (1074-12-0) + 2,2-dichloroacetophenone (2648-61-5) + S-methyl 2-oxo-2-phenylethanethioate (13603-60-6) + 1-chloroacetophenone (532-27-4,108321-66-0,164322-25-2)

Guidance literature:

With iodine; acetic acid; at 20 ℃; for 4h;

DOI:10.1039/c9cc00346k

Reference yield: 12.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + phenylacetylene (536-74-3) → phenylglyoxal hydrate (1074-12-0) + S-methyl 2-oxo-2-phenylethanethioate (13603-60-6) + 1-(1,2,2-triiodovinyl)benzene (16141-17-6) + (2,2-diiodo-1-phenylvinyl)(methyl)sulfane + 1-chloroacetophenone (532-27-4,108321-66-0,164322-25-2)

Guidance literature:

With iodine; glycine ethyl ester hydrochloride; at 80 ℃; for 2h;

DOI:10.1039/c9cc00346k

upstream raw materials:

phenylethane 1,2-diol

diethyl ether

chloroform

2,2-diiodo-1-phenylethan-1-one

Downstream raw materials:

(S)-Methyl mandelate

4-Phenylimidazole

1,3-dimethyl-7-phenyllumazine

2-hydroxy-2-(4-methylthiophenyl)-1-phenylethanone

Refernces

• 1、 Zhao, Peng,Yu, Xiao-Xiao,Zhou, You,Huang, Chun,Wu, Yan-Dong,Zhu, Yan-Ping,Wu, An-Xin. "Arylacetylenes as two-carbon synthons: Synthesis of eight-membered rings: Via CC bond cleavage". . p. 12554 - 12557. Retrieved 2020.
• 2、 Mehrabi, Hossein,Fadaei, Mohadeseh,Zadeh, Ashrafosadat Beheshti. "Four-component reaction of α-naphthol, an arylglyoxal, aniline and a dialkyl acetylenedicarboxylate: A Michael addition of enamines to α,β-unsaturated γ-dicarbonyl compounds". . p. 640 - 642. Retrieved 2016.
• 3、 Mishra, Richa,Jana, Asim,Panday, Anoop Kumar,Choudhury, Lokman H.. "Synthesis of fused pyrroles containing 4-hydroxycoumarins by regioselective metal-free multicomponent reactions". . p. 3289 - 3302. Retrieved 2018.
• 4、 Arfavi-Safari, Mona,Anaraki-Ardakani, Hossein,Badri, Rashid,Tahanpesar, Elham. "A highly efficient protocol for the synthesis of new 3-(α-aroylamido)-4-hydroxycoumarin derivatives using SnCl2-SiO2 nanoparticles under solventfree conditions". . p. 321 - 324. Retrieved 2017.
• 5、 Verhe, R.,Courtheyn, D.,Kimpe, N. De,Buyck, L. De,Schamp, N.. "Preparation of 1,1-Dialkoxy-2-alkanones". . p. 667 - 670. Retrieved 1982.
• 6、 Ballistreri, Francesco P.,Failla, Salvatore,Tomaselli, Gaetano A.,Curci, Ruggero. "A NEW FACILE SYNTHESIS OF α-DICARBONYL COMPOUNDS BY OXIDATION OF ALKYNES WITH Mo(VI) PEROXOCOMPLEX PROMOTED BY MERCURIC ACETATE". . p. 5139 - 5142. Retrieved 1986.
• 7、 Moehrle et al.. "". . p. 44,45. Retrieved 1973.
• 8、 Watanabe, Yoshihito,Numata, Tatsuo,Oae, Shigeru. "Oxidative S-Dealkylation Reaction of Sulfide Catalyzed by Co(II)(bzacen)". . p. 1915 - 1920. Retrieved 1982.
• 9、 Geng, Xiao,Wang, Can,Huang, Chun,Zhao, Peng,Zhou, You,Wu, Yan-Dong,Wu, An-Xin. "I2-Promoted Multicomponent Dicyclization and Ring-Opening Sequences: Direct Synthesis of Benzo[ e][1,4]diazepin-3-ones via Dual C-O Bond Cleavage". . p. 7504 - 7508. Retrieved 2019.
• 10、 Martinez, Yolanda,De Las Heras, Maria A.,Vaquero, Juan J.,Garcia-Navio, Jose L.,Alvarez-Builla, Julio. "1-(benzoylamino)-3-methylimidazolium chlorochromate (BAMICC), a new selective and mild reagent for the oxidation of allylic and benzylic alcohols". . p. 8513 - 8516. Retrieved 1995.