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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

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

Certificates of Analysis (COA)

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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)
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)
Phenylhydroxycarbene.
Gerbig D, et al.
Journal of the American Chemical Society, 132(21), 7273-7275 (2010)
Zhi-de Zhou et al.
International journal of biological macromolecules, 47(1), 21-26 (2010-04-20)
Saccharomyces cerevisiae alcohol dehydrogenase (SCAD) was effectively immobilized on hybrid alginate-chitosan beads which are hardened with glutaraldehyde. Immobilization conditions and characterization of the immobilized enzyme were investigated. Orthogonal test design and intuitive analysis method were employed to evaluate the effects
Forest H Andrews et al.
Bioorganic chemistry, 43, 26-36 (2012-01-17)
Thiamin diphosphate (ThDP) is the biologically active form of vitamin B(1), and ThDP-dependent enzymes are found in all forms of life. The catalytic mechanism of this family requires the formation of a common intermediate, the 2α-carbanion-enamine, regardless of whether the
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