Benzilic acid

Names
Preferred IUPAC name

Hydroxydi(phenyl)acetic acid[1]

Systematic IUPAC name

Hydroxydiphenylethanoic 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

CAS Number

* 76-93-7 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 521402
ChEBI |

* CHEBI:39414 Y

ChEMBL |

* ChEMBL578171 Y

ChemSpider |

* 6220 Y

ECHA InfoCard | 100.000.904
EC Number |

* 200-993-2

Gmelin Reference

| 281752

PubChem CID

* 6463

UNII |

* 8F6J993XXR

CompTox Dashboard (EPA)

* DTXSID0058805

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) Y

Key: UKXSKSHDVLQNKG-UHFFFAOYSA-N Y

* 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

Signal word

| Warning

Hazard statements

| H302

Precautionary statements

| 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).

N verify (what is YN ?)

Infobox references

Chemical compound

Benzilic acid is an organic compound with formula C
14H
12O
3 or (C

5)2(HO)C(COOH). It is a white crystalline aromatic acid, soluble in many primary alcohols.

## Contents

* 1 Preparation
* 2 Uses
* 3 References
* 4 External links

## Preparation[edit]

Benzilic acid can be prepared by a 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.[2]

## Uses[edit]

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]

## References[edit]

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.

## External links[edit]

* Safety MSDS data
* Solubility in alcohols
* Converting Benzaldehyde to Benzilic Acid
* Synthesis of Benzilic Acid

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H302]: H302: Harmful if swallowed
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P301+P312]: P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P330]: P330: Rinse mouth.
*[P501]: P501: Dispose of contents/container to ...