Benzilic acid
| 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
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| Identifiers | |
3D model (JSmol)
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| 521402 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
| 281752 | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 labelling: | |
| GHS07: Exclamation mark | |
| Warning | |
| H302 | |
| P264, P270, P301+P312, P330, P501 | |
| NFPA 704 (fire diamond) | |
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 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
[edit | edit source]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
[edit | edit source]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
[edit | edit source]- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ "Nerve Agent Precursors: Benzilic acid and Methyl Benzilate", Factsheets on Chemical and Biological Warfare Agents, Chemical precursors.
- ^ https://prepchem.com/synthesis-of-diphenylacetic-acid/
- ^ Systematic organic chemistry, by W. M. Cumming, 192-193, 1937.