Benzilic acid

Not to be confused with benzyl alcohol.
Benzilic acid
Skeletal formula of benzilic acid
Ball-and-stick model of the benzilic acid molecule
Names
Preferred IUPAC name
Hydroxydi(phenyl)acetic acid[1]
Other names
α,α-Diphenyl-α-hydroxyacetic acid, α,α-Diphenylglycolic acid, α-Hydroxydiphenyl acetic acid, 2,2-Diphenyl-2-hydroxyacetic acid, 2-Hydroxy-2,2-diphenylacetic acid, Diphenyl glycolic acid, Hydroxydiphenyl acetic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 521402
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.904
EC Number
  • 200-993-2
Gmelin Reference
 281752
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16) checkY
    Key: UKXSKSHDVLQNKG-UHFFFAOYSA-N checkY
  • InChI=1/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16)
    Key: UKXSKSHDVLQNKG-UHFFFAOYAV
SMILES
  • O=C(O)C(O)(c1ccccc1)c2ccccc2
Properties
Chemical formula
 C14H12O3
Molar mass 228.247 g·mol−1
Appearance white solid
Density 1.08 g/cm3
Melting point 150 to 152 °C (302 to 306 °F; 423 to 425 K)
Boiling point 180 °C (356 °F; 453 K) (17.3 hPa)
Solubility in water
 2 g/L (20 °C)
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H302
Precautionary statements
 P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Benzilic acid is an organic compound with formula C
14H
12O
3 or (C
6H
5)2(HO)C(COOH). It is a white crystalline aromatic acid, soluble in many primary alcohols.

Preparation

Benzilic acid can be prepared by heating a mixture of benzil, ethanol, and potassium hydroxide.

Another preparation, performed by Liebig in 1838, is the dimerization of benzaldehyde, to benzil, which is transformed to the product by the benzilic acid rearrangement reaction.[2]

Uses

Benzilic acid is used in the manufacture of glycollate pharmaceuticals including clidinium, dilantin, flutropium, and mepenzolate which are antagonists of the muscarinic acetylcholine receptors.

It is used in manufacture of the incapacitating agent 3-quinuclidinyl benzilate (BZ) which is regulated by the Chemical Weapons Convention. It is also monitored by law enforcement agencies of many countries, because of its use in the manufacture in hallucinogenic drugs.[3]

Benzilic acid can be reduced with hydroiodic acid to give diphenylacetic acid [117-34-0].[4][5]

References

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Liebig, J. (1838). "Ueber Laurent's Theorie der organischen Verbindungen". Annalen der Chemie. 25: 1–31. doi:10.1002/jlac.18380250102.
  3. ^ "Nerve Agent Precursors: Benzilic acid and Methyl Benzilate", Factsheets on Chemical and Biological Warfare Agents, Chemical precursors.
  4. ^ https://prepchem.com/synthesis-of-diphenylacetic-acid/
  5. ^ Systematic organic chemistry, by W. M. Cumming, 192-193, 1937.
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