Phenylglyoxylic acid

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of phenylglyoxylic acid
General
Surname Phenylglyoxylic acid
other names
  • Benzoyl formate
  • α-oxobenzoic acid
  • Benzoyl formic acid
  • 2-keto-2-phenylacetic acid ( IUPAC )
Molecular formula C 8 H 6 O 3
Brief description

off-white solid

External identifiers / databases
CAS number 611-73-4
EC number 210-278-7
ECHA InfoCard 100.009.345
PubChem 11915
ChemSpider 11421
DrugBank DB02279
Wikidata Q663909
properties
Molar mass 150.13 g mol −1
Physical state

firmly

density

1.38 g cm −3 (20 ° C)

Melting point

62-66 ° C

boiling point

147–151 ° C (16 hPa)

solubility
  • soluble in water
  • soluble in methanol (100 g l −1 at 20 ° C) and ethanol
  • poorly soluble in diethyl ether
  • insoluble in carbon disulfide
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319
P: 302 + 352-305 + 351 + 338
Toxicological data

180 mg kg −1 ( LD 50 ,  mouse ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phenylglyoxylic acid is a chemical compound from the group of carboxylic acids .

Extraction and presentation

Phenylglyoxylic acid can be obtained by oxidation of mandelic acid with potassium permanganate or by oxidation and subsequent saponification of methyl mandelate using lead (IV) acetate . An alternative synthesis is the hydrolysis of benzoyl cyanide .

properties

Phenylglyoxylic acid is an off-white, flammable solid that is soluble in water.

use

Phenylglyoxylic acid is used as a synthetic chemical to produce other chemical compounds.

Individual evidence

  1. ↑ a b c d e f g h i Datasheet phenylglyoxylic acid (PDF) from Merck , accessed on December 15, 2011.
  2. ↑ a b Datasheet Phenylglyoxylic acid, purum, ≥ 98.0% (T) from Sigma-Aldrich , accessed on December 15, 2011 ( PDF ).
  3. ↑ a b c David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. CRC Press, 2009, ISBN 978-1-4200-9084-0 .
  4. ^ BB Corson, Ruth A. Dodge, SA Harris, RK Hazen: Ethyl Benzoylformate In: Organic Syntheses . 8, 1928, p. 68, doi : 10.15227 / orgsyn.008.0068 ; Coll. Vol. 1, 1941, p. 241 ( PDF ).
  5. ↑ Erich Baer, ​​Morris Kates: A New Method of Preparing Phenylglyoxylic Acid and its Methyl Ester . In: Journal of the American Chemical Society . 67, September 1945, pp. 1482-1483. doi : 10.1021 / ja01225a022 .
  6. ^ TS Oakwood, CA Weisgerber: Benzoylformic Acid In: Organic Syntheses . 24, 1944, p. 16, doi : 10.15227 / orgsyn.024.0016 ; Coll. Vol. 3, 1955, p. 114 ( PDF ).