2-Phenylpropionic acid

Base Information

• Chemical Name: 2-Phenylpropionic acid
• CAS No.: 492-37-5
• Deprecated CAS: 2328-24-7
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.177
• Hs Code.: 29163900
• European Community (EC) Number: 207-752-0
• NSC Number: 245033,245032,42872
• UNII: CH15E393A2
• DSSTox Substance ID: DTXSID80862027
• Nikkaji Number: J313.188B,J2.433.032J
• Wikidata: Q27121253
• Metabolomics Workbench ID: 133036
• ChEMBL ID: CHEMBL370925
• Mol file: 492-37-5.mol

Synonyms:2-phenylpropionic acid;hydratropic acid;hydratropic acid, (+-)-isomer;hydratropic acid, (R)-isomer;hydratropic acid, (S)-isomer

Chemical Property of 2-Phenylpropionic acid

Chemical Property:

• Appearance/Colour: clear pale yellow to yellow liquid
• Vapor Pressure: 0.00601mmHg at 25°C
• Melting Point: 5 °C
• Refractive Index: n20/D 1.522(lit.)
• Boiling Point: 261 °C at 760 mmHg
• PKA: 4.34±0.10(Predicted)
• Flash Point: 154.3 °C
• PSA: 37.30000
• Density: 1.119 g/cm³
• LogP: 1.87470
• Storage Temp.: Store below +30°C.
• Solubility.: 9.9g/l
• Water Solubility.: 10 g/L (20 ºC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

(±)-2-PhenylpropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)C(=O)O
• Uses: 2-Phenylpropionic acid is used in the preparation of ibuprofen derivatives for their anti-inflammatory activity. Also used in nucleation inhibitors in Dutch resolution of diastereomers.

Technology Process of 2-Phenylpropionic acid

There total 232 articles about 2-Phenylpropionic 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: 99.2%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + carbon monoxide (201230-82-2) → hydratropic acid (492-37-5,2328-24-7)

Guidance literature:

With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% Ni/ZSM 5; In butanone; at 115 ℃; under 41372.9 Torr;

Reference yield: 99.0%

1-phenylethyl cyanide (1823-91-2) → hydratropic acid (492-37-5,2328-24-7)

Guidance literature:

With recombinant nitrilase from Pseudomonas fluorescens EBC 191; In methanol; phosphate buffer; at 25 ℃; pH=6;

DOI:10.1002/adsc.200600269

Reference yield: 99.0%

carbon monoxide (201230-82-2) + (1-chloroethyl)benzene (672-65-1) → hydratropic acid (492-37-5,2328-24-7)

Guidance literature:

With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% Ni/C; In butanone; at 115 ℃; under 41372.9 Torr;

upstream raw materials:

1-Phenylprop-1-yne

peracetic acid

ethylbenzene

potassium ethoxide

Downstream raw materials:

2-phenylpropionic acid methyl ester

ethyl 2-phenylpropanoate

2-(4-nitrophenyl)propanoic acid

2-phenylpropionyl chloride

Refernces

Trimethoxyphenyl compounds. IX. Boron heterocycles in preparative natural products chemistry: A simple synthesis of aurentiacin

10.1002/jlac.198219820810

The research focuses on the synthesis of aurentiacin and related compounds using boron heterocycles. Key chemicals involved include 2,4,6-trimethoxytoluene, which reacts with various acids such as cinnamic acid and 2-phenylpropionic acid in the presence of boron trifluoride to form boron heterocycles. These heterocycles are then hydrolyzed to yield aurentiacin (3b) and dihydroaurentiacin (3c). The study also explores the selective demethylation and acylation processes, highlighting the formation of intermediate compounds and their properties. The research provides a simple and efficient synthetic route for these natural products, with high yields and purity, contributing to the field of preparative natural products chemistry.