Benzilic acid

Benzilic acid
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
76-93-7 Yes
ChEBI CHEBI:39414 Yes
ChEMBL ChEMBL578171 Yes
ChemSpider 6220 Yes
Jmol-3D images Image
PubChem 6463
Properties
Molecular formula
 C14H12O3
Molar mass 228.24 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 R22
S-phrases 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 oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Benzilic acid is a white crystalline aromatic acid soluble in many primary alcohols. It can be prepared by heating mixture of benzil, alcohol and potassium hydroxide. The other preparation way is through benzaldehyde, which dimerizates to benzil and it is further transformed by benzilic acid rearrangement to benzilic acid. This reaction was also the first example of benzilic acid rearrangement performed by Liebig in 1838.[1]

Benzilic acid is used in organic synthesis, as a base point for preparation of glycollate pharmaceuticals and some hallucinogenic (deliriant) drugs – BZ, and Benactyzine being two examples.

See also

References

  1. ↑ Liebig, J. (1838). "Ueber Laurent's Theorie der organischen Verbindungen". Annalen der Chemie 25: 1–31. doi:10.1002/jlac.18380250102.

External links