Benzilic acid

Base Information

• Chemical Name: Benzilic acid
• CAS No.: 76-93-7
• Molecular Formula: C14H12O3
• Molecular Weight: 228.247
• Hs Code.: 29181980
• European Community (EC) Number: 200-993-2
• NSC Number: 2830
• UNII: 8F6J993XXR
• DSSTox Substance ID: DTXSID0058805
• Nikkaji Number: J4.188B
• Wikipedia: Benzilic_acid
• Wikidata: Q411740
• Metabolomics Workbench ID: 56297
• ChEMBL ID: CHEMBL578171
• Mol file: 76-93-7.mol

Synonyms:2,2-diphenyl-2-hydroxyethanoic acid;2-hydroxy-2,2-diphenylacetic acid;DPHEAc

Chemical Property of Benzilic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.01E-07mmHg at 25°C
• Melting Point: 149-151 °C(lit.)
• Refractive Index: 1.5805 (estimate)
• Boiling Point: 409 °C at 760 mmHg
• PKA: pKa (25°): 3.036
• Flash Point: 215.3 °C
• PSA: 57.53000
• Density: 1.279 g/cm³
• LogP: 2.00710
• Storage Temp.: Store below +30°C.
• Solubility.: 1.41g/l (experimental)
• Water Solubility.: 1.41 g/L (25 ºC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 228.078644241
• Heavy Atom Count: 17
• Complexity: 245

Purity/Quality:

99.9% ^*data from raw suppliers

Benzilic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 36-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C(=O)O)O
• Uses: Benzilic Acid is an impurity of Trospium (T892800), a tropine derivative with anticholinergic activity and a antiispasmodic agent.

Technology Process of Benzilic acid

There total 130 articles about Benzilic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

benzil (134-81-6) → Benzilic acid (76-93-7)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 0.5h; Heating;

Reference yield: 90.0%

benzaldehyde (100-52-7) → Benzilic acid (76-93-7)

Guidance literature:

With C₁₉H₃₂N₆O₄⁽²⁺⁾*2Br^(1-); sodium hydroxide; In acetonitrile; for 1.83333h; Reagent/catalyst; Catalytic behavior;

DOI:10.1002/jhet.2885

Reference yield: 87.0%

bromopropylate (18181-80-1) → Benzilic acid (76-93-7)

Guidance literature:

With methanol; gold; hydrogen; caesium carbonate; at 100 ℃; for 96h; under 3800.26 Torr;

DOI:10.1002/cctc.202000674

upstream raw materials:

benzophenone

1-methyl-4-nitrosobenzene

fluoro-diphenyl-acetic acid ethyl ester

benzoic acid ethyl ester

Downstream raw materials:

hydroxy-diphenyl-acetic acid 2-morpholin-4-yl-ethyl ester

benzilic acid-(2-piperidino-ethyl ester)

N,N-diphenylurea

bis(diphenyl)urea

Refernces

• 1、 Puterbaugh,Gaugh. "-". . p. 3513. Retrieved 1961.
• 2、 Roberts,Urey. "-". . p. 880. Retrieved 1938.
• 3、 Lachman. "-". . p. 779. Retrieved 1924.
• 4、 Okumura, Shintaro,Uozumi, Yasuhiro. "Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide". supporting information. p. 7194 - 7198. Retrieved 2021/09/22.
• 5、 Charpe, Vaibhav Pramod,Hwang, Kuo Chu,Sagadevan, Arunachalam. "Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature". supporting information. p. 4426 - 4432. Retrieved 2020/08/10.