2-Phenylbutyric acid

Base Information

• Chemical Name: 2-Phenylbutyric acid
• CAS No.: 90-27-7
• Deprecated CAS: 14375-30-5,7782-29-8
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Hs Code.: 29163900
• European Community (EC) Number: 201-982-5
• NSC Number: 1860
• UNII: S7S079H2C2
• DSSTox Substance ID: DTXSID90861682
• Nikkaji Number: J35.101F,J57.368J,J57.369H
• Wikidata: Q27159231
• NCI Thesaurus Code: C87750
• Metabolomics Workbench ID: 37206
• ChEMBL ID: CHEMBL1616045
• Mol file: 90-27-7.mol

Synonyms:2-phenylbutanoic acid;2-phenylbutyric acid

Chemical Property of 2-Phenylbutyric acid

Chemical Property:

• Appearance/Colour: white to yellowish adhering crystal
• Melting Point: 39-42 °C(lit.)
• Refractive Index: 1.5150
• Boiling Point: 272.9 °C at 760 mmHg
• PKA: 4.34±0.10(Predicted)
• Flash Point: 170.2 °C
• PSA: 37.30000
• Density: 1.09 g/cm³
• LogP: 2.26480
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: insoluble
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

99.9% ^*data from raw suppliers

2-Phenylbutyric acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C1=CC=CC=C1)C(=O)O
• Uses: 2-Phenylbutyric Acid is a metabolite of Butamirate. It exists in all living organisms, ranging from bacteria to humans. It is used as an antihyperlipidemic drug.

Technology Process of 2-Phenylbutyric acid

There total 93 articles about 2-Phenylbutyric 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: 96.0%

2-Phenylbutyryl chloride (36854-57-6) + C12H12O3 (1259078-94-8) → C22H22O4 (1259079-04-3) + 2-Phenylbutyric acid (90-27-7)

Guidance literature:

2-Phenylbutyryl chloride; C₁₂H₁₂O₃; With dmap; In dichloromethane; at 20 ℃; for 15h; Inert atmosphere;

With sodium carbonate; In dichloromethane; water;

In water; pH=3; optical yield given as %de; Acidic conditions;

DOI:10.1039/c0cc02689a

Reference yield: 85.0%

1-propenylbenzene (873-66-5) + carbon monoxide (201230-82-2) → 2-Phenylbutyric acid (90-27-7)

Guidance literature:

With water; bis-triphenylphosphine-palladium(II) chloride; In butanone; at 115 ℃; for 2h; under 40504.1 Torr;

DOI:10.1021/ol990665+

Reference yield: 78.0%

1-phenylethyl (S)-2-phenylbutanoate → (S)-1-phenylethanol (1445-91-6) + (R)-1-phenylethanol (1517-69-7) + 2-Phenylbutyric acid (90-27-7)

Guidance literature:

1-phenylethyl (S)-2-phenylbutanoate; With sodium ethanolate; In tetrahydrofuran;

With water; dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; optical yield given as %ee;

DOI:10.1016/j.tetlet.2009.05.046

upstream raw materials:

diethyl ether

methylammonium carbonate

1-methyl-4-nitrosobenzene

(S)-2-phenylbutyramide

Downstream raw materials:

3-phenyl-2-pentanone

2-(1-hydroxy-cyclohexyl)-2-phenyl-butyric acid

2-phenyl-butyric acid-(2-dimethylamino-ethyl ester)

1.4-Bis-<2-(2-phenyl-butyryl-oxy)-ethyl>-piperazin

Refernces

• 1、 Hofer, O.,Schloegl, K.. "". . p. 457 - 468. Retrieved 1968.
• 2、 Roy, Avijit,Oestreich, Martin. "Metal-Free Hydrosilylation of Ketenes with Silicon Electrophiles: Access to Fully Substituted Aldehyde-Derived Silyl Enol Ethers". supporting information. p. 8273 - 8276. Retrieved 2021/05/11.
• 3、 Comba, Peter,Ghosh, Tamal,Hashmi, A. Stephen K.,Krieg, Saskia,Menche, Maximilian,Paciello, Rocco,Rück, Katharina S. L.,Sabater, Sara,Sch?fer, Ansgar,Schaub, Thomas. "Mechanistic Investigation of the Nickel-Catalyzed Carbonylation of Alcohols". supporting information. . Retrieved 2020/03/19.