B13055
Phenylglyoxylic acid
97%
Synonym(s):
α-Oxophenylacetic acid, Benzoylformic acid
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About This Item
Linear Formula:
C6H5COCOOH
CAS Number:
Molecular Weight:
150.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-278-7
Beilstein/REAXYS Number:
606718
MDL number:
Assay:
97%
Form:
crystals
InChI key
FAQJJMHZNSSFSM-UHFFFAOYSA-N
InChI
1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
SMILES string
OC(=O)C(=O)c1ccccc1
assay
97%
form
crystals
mp
62-65 °C (lit.)
Quality Level
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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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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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