Compound: BENZILIC ACID
SMILES: O=C(O)C(O)(c1ccccc1)c2ccccc2
InChIKey: UKXSKSHDVLQNKG-UHFFFAOYSA-N
Synonyms: BENZILIC ACID, 76-93-7, Diphenylglycolic acid, 2-Hydroxy-2,2-diphenylacetic acid, Benzylic acid, Diphenylhydroxyacetic acid, Hydroxydiphenylacetic acid, Glycolic acid, diphenyl-, Acide diphenylhydroxyacetique, Benzilsaeure, 2,2-Diphenyl-2-hydroxyacetic acid, alpha-Hydroxy-alpha-phenylbenzeneacetic acid, alpha-Hydroxy-2,2-diphenylacetic acid, NSC 2830, Mandelic acid, alpha-phenyl-, alpha-phenylmandelic acid, alpha,alpha-Diphenylglycolic acid, EINECS 200-993-2, UNII-8F6J993XXR, Acide diphenylhydroxyacetique [French], BRN 0521402, 8F6J993XXR, Mandelic acid, .alpha.-phenyl-, Benzeneacetic acid, .alpha.-hydroxy-.alpha.-phenyl-, AI3-06300, HSDB 7709, NSC-2830, Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, .alpha.,.alpha.-Diphenylglycolic acid, BENZILIC ACID [MI], .alpha.-Hydroxy-2,2-diphenylacetic acid, BENZILIC ACID [HSDB], alpha,alpha-Diphenyl-alpha-hydroxyacetic acid, DTXSID0058805, CHEBI:39414, .alpha.-Hydroxydiphenylacetic acid, .alpha.-Hydroxy-.alpha.-phenylbenzeneacetic acid, 4-10-00-01256 (Beilstein Handbook Reference), .alpha.,.alpha.-Diphenyl-.alpha.-hydroxyacetic acid, TROSPIUM CHLORIDE IMPURITY A [EP IMPURITY], ACIDE DIPHENYLHYDROXYACETIQUE (FRENCH), TROSPIUM CHLORIDE IMPURITY A (EP IMPURITY), Hydroxydiphenyl acetic acid, Glycolic acid, diphenyl, RefChem:118136, Mandelic acid, alphaphenyl, BENZILIC ACID [INCI], 2,2Diphenyl2hydroxyacetic acid, alpha-Hydroxydiphenylacetic acid, alphaalpha Diphenylglycolic acid, DTXCID9047837, alphaHydroxy2,2diphenylacetic acid, ALPHA-ALPHA-DIPHENYLGLYCOLIC ACID, alphaHydroxyalphaphenylbenzeneacetic acid, alphaHydroxyalphaphenyl benzeneacetic acid, Benzeneacetic acid, alphahydroxyalphaphenyl, ALPHA-HYDROXY-ALPHA-PHENYL BENZENEACETIC ACID, DIPHENYL-HYDROXY-ACETIC ACID (BENZILIC ACID), 200-993-2, 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, UKXSKSHDVLQNKG-UHFFFAOYSA-N, hydroxy(diphenyl)acetic acid, MFCD00004447, 2-hydroxy-2,2-diphenyl-acetic acid, Benzillic acid, 4hnc, Trospium impurity A CRS, Benzilic acid, >=99%, SCHEMBL7066, Hydroxydi(phenyl)acetic acid, Oprea1_231381, SCHEMBL72162, CHEMBL578171, SCHEMBL11243452, SCHEMBL28975532, BDBM81768, NSC2830, BBL013081, ICCB1_000122, SBB003299, STK315343, AKOS000120948, MSK70026-100W, FB38835, MSK70026-1000W, NSC_5311391, NCGC00165988-01, AC-13764, VS-03659, alpha-phenyl-alpha-hydroxyphenylacetic acid, CAS_6581-06-2, Benzilic acid Solution in Water, 100ug/mL, B0052, NS00037863, ST45138014, Benzilic acid Solution in Water, 1000ug/mL, Q411740, SR-01000400770, SR-01000400770-1, DIPHENYL-HYDROXY-ACETIC ACID  (BENZILIC ACID), Trospium impurity A, European Pharmacopoeia (EP) Reference Standard, 0UT
Theoretical properties:
molecular_formula: C14H12O3
molecular_weight: 228.24 g/mol
exact_mass: 228.078644241 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 17
topological_polar_surface_area: 57.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to tan powder
color: White to tan powder
odor: Characteristic odor
boiling_point: 180 °C
melting_point: 150 °C
solubility: Very soluble in ethanol, ethyl ether; soluble concentrated sulfuric acid; slightly soluble in acetone
vapor_pressure: 0.00000002 [mmHg]
Descriptions:
pubchem: Benzilic acid is a 2-hydroxy monocarboxylic acid.
chembl: BENZYLIC ACID is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid. First performed by Justus von Liebig in 1838, it is the first reported example of a rearrangement reaction. It has become a classic reaction in organic synthesis and has been reviewed many times before. It can be viewed as an intramolecular redox reaction, as one carbon center is oxidized while the other is reduced.

The reaction has been shown to work in aromatic, semi-aromatic, aliphatic, and heterocyclic substrates. The reaction works best when the ketone functional groups have no adjacent enolizable protons, as this allows aldol condensation to compete. The reaction is formally a ring contraction when used on cyclic diketones. It has been found that aryl groups more readily migrate than alkyl groups, and that aryl groups with electron-withdrawing groups migrate the fastest.