Benzilic acid

Last updated
Benzilic acid
Benzilsaure.svg
Benzilic-acid-3D-balls.png
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
3D model (JSmol)
521402
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.904 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-993-2
281752
PubChem CID
UNII
  • 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) Yes check.svgY
    Key: UKXSKSHDVLQNKG-UHFFFAOYSA-N Yes check.svgY
  • 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
  • O=C(O)C(O)(c1ccccc1)c2ccccc2
Properties
C14H12O3
Molar mass 228.247 g·mol−1
Appearancewhite 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)
2 g/L (20 °C)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302
P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.