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B13055

Sigma-Aldrich

Phenylglyoxylic acid

97%

Synonym(s):

α-Oxophenylacetic acid, Benzoylformic acid

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About This Item

Linear Formula:
C6H5COCOOH
CAS Number:
611-73-4
Molecular Weight:
150.13
Beilstein:
606718
EC Number:
210-278-7
MDL number:
MFCD00002575
UNSPSC Code:
12352100
PubChem Substance ID:
24891579
NACRES:
NA.22

Quality Level

200

Assay

97%

form

crystals

mp

62-65 °C (lit.)

SMILES string

OC(=O)C(=O)c1ccccc1

InChI

1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)

InChI key

FAQJJMHZNSSFSM-UHFFFAOYSA-N

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Application

Phenylglyoxylic acid can be used as a precursor in the synthesis of:
  • O-acyl acetanilides by decarboxylative o-acylation of acetanilides using Pd catalyst.
  • Phenylhydroxycarbene by high-vacuum flash pyrolysis.
  • 2-arylbenzothiazoles by reacting with o-aminothiophenol using ammonium niobium oxalate (ANO) as a catalyst.
  • 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones by treating with o-aminophenol in the presence of ammonium niobium oxalate catalyst.
  • 2-aryl benzothiazoles through potassium persulfate (K2S2O8)-mediated oxidative condensation of benzothiazoles.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF8498
BCBX6369
BCBW0405
BCBP4353V
BCBD4269V

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Phenylhydroxycarbene.
Gerbig D, et al.
Journal of the American Chemical Society, 132(21), 7273-7275 (2010)
Room temperature palladium-catalyzed decarboxylative ortho-acylation of acetanilides with ?-oxocarboxylic acids.
Fang P, et al.
Journal of the American Chemical Society, 132(34), 11898-11899 (2010)
Niobium-promoted reaction of ?-phenylglyoxylic acid with ortho-functionalized anilines: synthesis of 2-arylbenzothiazoles and 3-aryl-2 H-benzo [b][1, 4] benzoxazin-2-ones
Penteado F, et al.
Green Chemistry, 18(24), 6675-6680 (2016)
Jesus M Aizpurua et al.
The Journal of organic chemistry, 74(17), 6691-6702 (2009-08-01)
Mechanistic details of the Mg(2+) ion-activated enantioselective reduction of methyl benzoylformate have been investigated at a B3LYP/6-31G* theory level, using peptide NADH models 1 rigidified with a beta-lactam ring. Computation of the reaction pathway revealed important structural differences between the
Caleb J Allpress et al.
Journal of the American Chemical Society, 135(2), 659-668 (2012-12-12)
Mononuclear Fe(II) complexes ([(6-Ph(2)TPA)Fe(PhC(O)C(R)C(O)Ph)]X (3-X: R = OH, X = ClO(4) or OTf; 4: R = H, X = ClO(4))) supported by the 6-Ph(2)TPA chelate ligand (6-Ph(2)TPA = N,N-bis((6-phenyl-2-pyridyl)methyl)-N-(2-pyridylmethyl)amine) and containing a β-diketonate ligand bound via a six-membered chelate ring
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