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Benzoylformic acid

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Benzoylformic acid Basic information
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
  • pka2.15±0.54(Predicted)
  • form Adhering Crystals, Crystalline Powder or Chunks
  • color White to light yellow
  • Water Solubility very faint turbidity
  • BRN 606718
  • InChIKeyFAQJJMHZNSSFSM-UHFFFAOYSA-N
  • CAS DataBase Reference611-73-4(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzoylformic acid(611-73-4)
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
  • ToxicityLD50 ivn-mus: 180 mg/kg CSLNX* NX#04110
MSDS
Benzoylformic acid Usage And Synthesis
  • Chemical Propertieswhite to light yellow adhering crystals,
  • DefinitionChEBI: 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 ProfileA poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating vapors.
  • Purification MethodsIf 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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