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Benzoylformic acid

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Benzoylformic acid Basic information

Product Name:
Benzoylformic acid
Synonyms:
  • PHENYLGLYOXYLIC ACID
  • OXO(PHENYL)ACETIC ACID
  • RARECHEM AL BO 0070
  • Benzeneacetic acid, a-oxo-
  • Phenylglyoxylic acid purum, >=98.0% (T)
  • BenzoylforMic acid, 97.5%
  • 2-Oxo-2-phenylacetic acid
  • alpha-Ketophenylacetic acid
CAS:
611-73-4
MF:
C8H6O3
MW:
150.13
EINECS:
210-278-7
Product Categories:
  • Aromatics
  • Aromatic Phenylacetic Acids and Derivatives
  • Halogenated Heterocycles ,Pyrazines ,Pyrans
Mol File:
611-73-4.mol
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Benzoylformic acid Chemical Properties

Melting point:
62-65 °C(lit.)
Boiling point:
84 °C0.1 mm Hg
Density 
1.38
refractive index 
1.4500 (estimate)
Flash point:
147-151°C/12mm
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
methanol: 0.1 g/mL, clear
pka
2.15±0.54(Predicted)
form 
Adhering Crystals, Crystalline Powder or Chunks
color 
White to light yellow
Water Solubility 
very faint turbidity
BRN 
606718
InChIKey
FAQJJMHZNSSFSM-UHFFFAOYSA-N
CAS DataBase Reference
611-73-4(CAS DataBase Reference)
NIST Chemistry Reference
Benzoylformic acid(611-73-4)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-28-36-28A-24-22-37
WGK Germany 
3
RTECS 
DA1480000
HS Code 
29183000
Toxicity
LD50 ivn-mus: 180 mg/kg CSLNX* NX#04110

MSDS

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Benzoylformic acid Usage And Synthesis

Chemical Properties

white to light yellow adhering crystals,

Uses

Phenylglyoxylic Acid (cas# 611-73-4) is a compound useful in organic synthesis.

Uses

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.

Definition

ChEBI: A 2-oxo monocarboxylic acid that is glyoxylic acid in which the aldehyde hydrogen is substituted by a phenyl group.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 26, p. 1631, 1983 DOI: 10.1021/jm00365a015
Organic Syntheses, Coll. Vol. 1, p. 241, 1941
Tetrahedron Letters, 17, p. 3735, 1976 DOI: 10.1016/S0040-4039(00)93096-X

Safety Profile

A poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating vapors.

Synthesis

The synthesis of Benzoylformic acid is as follows:Acetophenone (120 g, 1 mol) was dissolved in 2000 ml of pyridine, and 165 g (1.5 mol) of selenium dioxide was added under stirring.The mixture was refluxed for 3 hours and left to cool overnight.Filter through celite, wash the filter cake with xylene, and combine the filtrate and washings with azeotropic evaporation.The evaporated residue was dissolved in 1 L of ethyl acetate and washed with 300 ml of 10% dilute hydrochloric acid.The organic layer was washed with 400 ml of 5% sodium hydroxide solution, and the washed aqueous layer was adjusted to pH 2-3 with 10% dilute hydrochloric acid.A white solid precipitates, is filtered, the filter cake is washed with water, and dried to obtain 120 g of a white solid.Yield: 87%, purity: 99.2%.

Purification Methods

If the sample is oily, then it may contain H2O. In this case dry it in a vacuum desiccator over P2O5 or KOH until crisp. For further purification dissolve 5.5g in hot CCl4 (750mL), add charcoal (2g, this is necessary otherwise the acid may separate as an oil), filter, cool in ice-water until crystallisation is complete. Filter the acid off, and the solvent on the crystals is removed by keeping the acid (4.5g) in a vacuum desiccator for 2 days. Slightly yellow crystals are obtained. It can be recrystallised also from *C6H6/pet ether, and can be distilled in a vacuum. The acid is estimated by titration with standard NaOH. The phenylhydrazone is recrystallised from EtOH, m 163-164o, and the semicarbazone acid has m 259o(dec) (from EtOH). The methyl ester distils at 137o/14mm, 110-111o/2mm, n 20 1.5850. [Baert & Kates J Am Chem Soc 67 1482 1945, Schaffer & Corey J Org Chem 24 1825 1959, Beilstein 10 H 654, 10 IV 2737.]

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