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Benzilic acid

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Name

Benzilic acid

EINECS 200-993-2
CAS No. 76-93-7 Density 1.279 g/cm3
PSA 57.53000 LogP 2.00710
Solubility 1.41 g/L (25 ºC) Melting Point 149-151 °C(lit.)
Formula C14H12O3 Boiling Point 409 °C at 760 mmHg
Molecular Weight 228.247 Flash Point 215.3 °C
Transport Information N/A Appearance white powder
Safety 36/37/39-26 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 76-93-7 (Benzilic acid) Hazard Symbols HarmfulXn
Synonyms

2-Hydroxy-2,2-diphenylaceticacid;Diphenylhydroxyacetic acid;a,a-Diphenyl-a-hydroxyacetic acid;a-Hydroxy-2,2-diphenylacetic acid;a-Hydroxydiphenylacetic acid;

Article Data 164

Benzilic acid Synthetic route

119-61-9

benzophenone

124-38-9

carbon dioxide

76-93-7

Benzilic acid

Conditions
ConditionsYield
With tetrabutylammomium bromide In acetonitrile Electrochemical reaction; Irradiation;98%
With Tetrapropylammonium chloride In acetonitrile at 20℃; under 760.051 Torr; for 10h; Electrochemical reaction;90%
With potassium iodide In N,N-dimethyl-formamide Hg pool cathode, platinum plate anode, constant current of 2.5 nA/cm2;86%
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 20℃; electrochemical reaction;75%
With tetrabutylammonium halide In N,N-dimethyl-formamide Ambient temperature; electrolysis, Mg anode;70%
134-81-6

benzil

76-93-7

Benzilic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water for 0.5h; Heating;97%
With water; sodium hydroxide In ethanol for 0.5h; Reflux;97%
Stage #1: benzil With N-benzyl-trimethylammonium hydroxide at 40℃; for 4h;
Stage #2: With hydrogenchloride In water pH=3;
92%
64-95-9

adiphenine

76-93-7

Benzilic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol at 65℃;92%
13249-75-7

(Z)-1,2,4-triphenyl-2-butene-1,4-dione

119-53-9

2-hydroxy-2-phenylacetophenone

A

4441-01-4

1,2,4-triphenylbutane-1,4-dione

B

76-93-7

Benzilic acid

C

134-81-6

benzil

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide for 2h; Mechanism; Ambient temperature; other reaction conditions, other substrates;A 91%
B n/a
C n/a
100-52-7

benzaldehyde

76-93-7

Benzilic acid

Conditions
ConditionsYield
With C19H32N6O4(2+)*2Br(1-); sodium hydroxide In acetonitrile for 1.83333h; Catalytic behavior; Reagent/catalyst;90%
Stage #1: benzaldehyde With oxygen; 1-butyl-3-methylimidazolium Tetrafluoroborate; potassium hydroxide at 60℃; for 0.416667h; Neat (no solvent); Microwave irradiation;
Stage #2: With hydrogenchloride In water at 20℃;
74%
18181-80-1

bromopropylate

76-93-7

Benzilic acid

Conditions
ConditionsYield
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 96h;87%
62217-32-7

2-diphenylmethylene-1,3-benzodithiole

A

6461-76-3

1,2-benzenedisulfonyl dichloride

B

76-93-7

Benzilic acid

Conditions
ConditionsYield
With chlorine In water; tert-butyl alcohol at 0 - 5℃; for 2h; Yields of byproduct given;A n/a
B 85%
With chlorine In water; tert-butyl alcohol at 0 - 5℃; for 2h; Yield given;A n/a
B 85%
3240-34-4

[bis(acetoxy)iodo]benzene

3469-00-9

methyl 2,2-diphenylacetate

76-93-7

Benzilic acid

Conditions
ConditionsYield
With potassium hydroxide In water; benzene75%

A

76-93-7

Benzilic acid

B

65-85-0

benzoic acid

Conditions
ConditionsYield
Stage #1: 1,2-diphenyl-1,2-ethanediol With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 760.051 Torr; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; Reagent/catalyst; Solvent; chemoselective reaction;
A 10%
B 74%
451-40-1

phenyl benzyl ketone

A

106-47-8

4-chloro-aniline

B

76-93-7

Benzilic acid

C

65-85-0

benzoic acid

Conditions
ConditionsYield
With nitrobenzene In potassium hydroxide; tert-butyl alcohol for 0.5h; Heating;A 71%
B 58%
C 24%

Benzilic acid Consensus Reports

Reported in EPA TSCA Inventory.

Benzilic acid Specification

The Benzilic acid with CAS registry number of 76-93-7 is also called Benzeneacetic acid,a-hydroxy-a-phenyl-. Its EINECS registry number is 200-993-2. The IUPAC name is 2-hydroxy-2,2-diphenylacetic acid. In addition, the molecular formula is C14H12O3 and the molecular weight is 228.24. It is a kind of a white crystalline aromatic acid and soluble in many primary alcohols. In addition, it belongs to the classes of Pharmaceutical Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organics.

Physical properties about this chemical are: (1)ACD/LogP: 3.03; (2)ACD/LogD (pH 5.5): 0.14; (3)ACD/LogD (pH 7.4): -0.69; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1.37; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 35.53 Å2; (12)Index of Refraction: 1.622; (13)Molar Refractivity: 62.87 cm3; (14)Molar Volume: 178.3 cm3; (15)Polarizability: 24.92 ×10-24cm3; (16)Surface Tension: 56.3 dyne/cm; (17)Density: 1.279 g/cm3; (18)Flash Point: 215.3 °C; (19)Enthalpy of Vaporization: 69.71 kJ/mol; (20)Boiling Point: 409 °C at 760 mmHg; (21)Vapour Pressure: 2.01E-07 mmHg at 25°C.

Preparation of Benzilic acid: It can be prepared by heating mixture of benzil, alcohol and potassium hydroxide. And it can be prepared by diphenylethanedione. This reaction will need reagent NaOH and solvents ethanol and H2O. The reaction time is 30 minutes by heating at reaction. The yield is about 97%.

Benzilic acid can be prepared by diphenylethanedione

Uses of Benzilic acid: it can be used to determine the zirconium. And it can be used to get benzophenone. This reaction will need reagents sodium metavanadate and 70percent aq.HClO4. The reaction time is 10 minutes by heating. The yield is about 80%.

Benzilic acid can be used to get benzophenone

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C(O)(c1ccccc1)c2ccccc2
(2)InChI: 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)
(3)InChIKey: UKXSKSHDVLQNKG-UHFFFAOYAV

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 2gm/kg (2000mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 116, Pg. 154, 1958.
mouse LD50 subcutaneous 1300mg/kg (1300mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 116, Pg. 154, 1958.

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