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Benzilic acid

Topic: Chemistry

 From HandWiki - Reading time: 2 min
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
3D model (JSmol)
521402
ChEBI
ChEMBL
ChemSpider
EC Number
  • 200-993-2
281752
UNII
Properties
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)
2 g/L (20 °C)
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H302
P264, P270, P301+312, P330, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondFlammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzilic acid is an organic compound with formula C14H12O3 or (C6H5)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. https://zenodo.org/record/1426927. 
  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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