Benzilic acid

Benzilic acid
Skeletal formula of benzilic acid
Ball-and-stick model of the benzilic acid molecule
Names
IUPAC name
Hydroxy(diphenyl)acetic acid
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.904
Properties
C14H12O3
Molar mass 228.25 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
R-phrases (outdated) R22
S-phrases (outdated) S23, S24, S25, S28, S36, S37, S45
NFPA 704
Flammability 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 codeNFPA 704 four-colored diamond
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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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 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.[1]

Uses

Benzilic acid is used in the manufacture of glycollate pharmaceuticals including Clidinium, Dilantin, and Flutropium, which are antagonists of the muscarinic acetylcholine receptors.

It is used in manufacture of the incapacitating agent 3-quinuclidinyl benzilate (BZ) and 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.[2]

References

  1. ↑ Liebig, J. (1838). "Ueber Laurent's Theorie der organischen Verbindungen". Annalen der Chemie. 25: 1–31. doi:10.1002/jlac.18380250102.
  2. ↑ "Nerve Agent Precursors: Benzilic acid and Methyl Benzilate", Factsheets on Chemical and Biological Warfare Agents, Chemical precursors.
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