2-(4-Isobutylphenyl)-2-hydroxypropionic Acid

Base Information

• Chemical Name: 2-(4-Isobutylphenyl)-2-hydroxypropionic Acid
• CAS No.: 60057-62-7
• Molecular Formula: C13H18O3
• Molecular Weight: 222.284
• Hs Code.: 2918199090
• European Community (EC) Number: 641-443-5
• UNII: 72Z1R0AQ22
• DSSTox Substance ID: DTXSID20874462
• Nikkaji Number: J27.594H
• Wikidata: Q27266107
• Mol file: 60057-62-7.mol

Synonyms:60057-62-7;rac alpha-Hydroxy Ibuprofen;2-(4-Isobutylphenyl)-2-hydroxypropionic Acid;Ibuprofen Impurity M;rac a-Hydroxy Ibuprofen;2-hydroxy-2-[4-(2-methylpropyl)phenyl]propanoic Acid;2-(p-Isobutylphenyl)lactic Acid;2-Hydroxy-2-(4-isobutylphenyl)propionic Acid;(2RS)-2-Hydroxy-2-(4-(2-methylpropyl)phenyl)propanoic acid;2-(p-Isobutylphenyl)-2-hydroxypropionic acid;2-hydroxy-2-(4-isobutylphenyl)propanoic acid;72Z1R0AQ22;(+/-)-2-Hydroxy-2-(4-(2-methylpropyl)phenyl)propanoic acid;(2RS)-2-Hydroxy-2-[4-(2-methylpropyl)phenyl]propanoic Acid;rac |A-Hydroxy Ibuprofen;Ibuprofen impurity M [EP];UNII-72Z1R0AQ22;hydroxy-ibuprofen;IbuprofenImpurityM;alpha-Hydroxy ibuprofen, (+/-)-;Ibuprofen Imp. M (EP);rac ?-Hydroxy Ibuprofen;rac alpha -Hydroxy Ibuprofen;SCHEMBL7323204;DTXSID20874462;APEODKDQAWQDLW-UHFFFAOYSA-N;Benzeneacetic acid, alpha-hydroxy-alpha-methyl-4-(2-methylpropyl)-;MFCD03414226;RAC .ALPHA.-HYDROXY IBUPROFEN;AKOS010486957;IBUPROFEN IMPURITY M [EP IMPURITY];FT-0669667;.ALPHA.-HYDROXY IBUPROFEN, (+/-)-;2-(4-isobutyl-phenyl)-2-hydroxy-propionic acid;Q27266107;BENZENEACETIC ACID, 4-isoBUTYL-a-HYDROXY-a-METHY;2-hydroxy-2-[4-(2-methyl-propyl)-phenyl]-propionic acid;BENZENEACETIC ACID, .ALPHA.-HYDROXY-.ALPHA.-METHYL-4-(2-METHYLPROPYL)-;82412-82-6

Chemical Property of 2-(4-Isobutylphenyl)-2-hydroxypropionic Acid

Chemical Property:

• Melting Point: 95-97°C
• Boiling Point: 367.9±27.0 °C(Predicted)
• PKA: 3.62±0.25(Predicted)
• PSA: 57.53000
• Density: 1.122±0.06 g/cm3(Predicted)
• LogP: 2.17720
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 222.125594432
• Heavy Atom Count: 16
• Complexity: 242

Purity/Quality:

98%Min ^*data from raw suppliers

racα-HydroxyIbuprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1=CC=C(C=C1)C(C)(C(=O)O)O
• Uses: A potential precursor of Ibuprofen and Naproxen. Antiinflammatory agent.

Technology Process of 2-(4-Isobutylphenyl)-2-hydroxypropionic Acid

There total 19 articles about 2-(4-Isobutylphenyl)-2-hydroxypropionic 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: 98.0%

methyl 2-hydroxy-2-(4-isobutylphenyl)propionate (101970-32-5) → 2-(4-isobutyl-phenyl)-2-hydroxy-propionic acid (60057-62-7)

Guidance literature:

With ethanol; potassium hydroxide; at 20 ℃; for 4h;

DOI:10.1002/anie.201308698

Reference yield: 92.0%

carbon dioxide (124-38-9,18923-20-1) + 1-(4-isobutyl-phenyl)-ethanone (38861-78-8) → 2-(4-isobutyl-phenyl)-2-hydroxy-propionic acid (60057-62-7)

Guidance literature:

With Tetrapropylammonium chloride; In acetonitrile; at 20 ℃; for 10h; under 760.051 Torr; Reagent/catalyst; Solvent; Temperature; Electrochemical reaction;

DOI:10.14233/ajchem.2021.23090

Reference yield: 90.0%

2-hydroxy-2-(4-iso-butylphenyl)propanenitrile (63367-12-4) → 2-(4-isobutyl-phenyl)-2-hydroxy-propionic acid (60057-62-7)

Guidance literature:

With hydrogenchloride; water; In 1,4-dioxane; Reflux;

DOI:10.1016/j.tet.2009.01.005

upstream raw materials:

chloroform

1-(4-isobutyl-phenyl)-ethanone

trichlorofluoromethane

ethyl 2-(4-isobutylphenyl)-2-hydroxypropanoate

Downstream raw materials:

ibuprofen

2-(4-isobutylphenyl)acrylic acid

1-(4-isobutyl-phenyl)-ethanone

Refernces

• 1、 Lesieur, Mathieu,Genicot, Christophe,Pasau, Patrick. "Development of a Flow Photochemical Aerobic Oxidation of Benzylic C-H Bonds". supporting information. p. 1987 - 1990. Retrieved 2018/04/16.
• 2、 Musmarra, Dino,Prisciandaro, Marina,Capocelli, Mauro,Karatza, Despina,Iovino, Pasquale,Canzano, Silvana,Lancia, Amedeo. "Degradation of ibuprofen by hydrodynamic cavitation: Reaction pathways and effect of operational parameters". . p. 76 - 83. Retrieved 2015/09/28.