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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Sirilak Wongvijitsuk et al.
International journal of hygiene and environmental health, 214(2), 127-137 (2010-10-30)
The present study aimed to evaluate the effects of styrene exposure at levels below the recommended standards of the Threshold Limit Value (TLV-TWA(8)) of 20 ppm (ACGIH, 2004) in reinforced-fiberglass plastics workers. Study subjects comprised 50 exposed workers and 40
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
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