Phenylpropiolic acid

Base Information

• Chemical Name: Phenylpropiolic acid
• CAS No.: 637-44-5
• Molecular Formula: C9H6 O2
• Molecular Weight: 146.145
• Hs Code.: 29163900
• European Community (EC) Number: 211-285-8
• NSC Number: 13669
• UNII: 4KE28XZ9GX
• DSSTox Substance ID: DTXSID7060918
• Nikkaji Number: J134.378E
• Wikipedia: Phenylpropiolic_acid
• Wikidata: Q7181437
• Metabolomics Workbench ID: 38139
• ChEMBL ID: CHEMBL4059878
• Mol file: 637-44-5.mol

Synonyms:phenylpropiolic acid

Chemical Property of Phenylpropiolic acid

Chemical Property:

• Appearance/Colour: Slightly beige crystalline powder.
• Vapor Pressure: 0.000433mmHg at 25°C
• Melting Point: 135-137 °C(lit.)
• Refractive Index: 1.5550 (estimate)
• Boiling Point: 302.6 °C at 760 mmHg
• PKA: pK1:2.269 (35°C)
• Flash Point: 151 °C
• PSA: 37.30000
• Density: 1.24 g/cm³
• LogP: 1.12270
• Storage Temp.: 0-6°C
• Water Solubility.: freely soluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 146.036779430
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

99% ^*data from raw suppliers

Phenylpropiolic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC(=O)O
• Uses: Phenylpropiolic Acid is used as a reagent in the high yield synthesis of 3,3-diphenylpropanoic acid derivatives via hydrophenylation and ionic hydrogenation with strong Lewis acids. It is also used in the synthesis of highly substituted aromatic rings via the alkyne-mediated approach which serve as templates for drug design.

Technology Process of Phenylpropiolic acid

There total 122 articles about Phenylpropiolic 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: 100.0%

carbon dioxide (124-38-9,18923-20-1) + phenylacetylene (536-74-3) → phenylpropyolic acid (637-44-5)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 50 ℃; for 24h; under 760.051 Torr; Reagent/catalyst; Temperature; Catalytic behavior;

DOI:10.1039/c8ta04667k

Reference yield: 98.0%

carbon dioxide (1111-72-4) + phenylacetylene (536-74-3) → phenylpropyolic acid (637-44-5)

Guidance literature:

carbon dioxide; phenylacetylene; With diethoxymethylane; potassium tert-butylate; at 40 ℃; for 2h; Schlenk technique;

With hydrogenchloride; In water; Reagent/catalyst; Schlenk technique;

DOI:10.1007/s11426-017-9163-2

Reference yield: 97.0%

4-((tert-butyldimethylsilyl)oxy)benzyl 3-phenylpropiolate → phenylpropyolic acid (637-44-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2019.05.039

upstream raw materials:

n-butyllithium

diethyl ether

bromostyrene

3-phenyl-4,4-dichloro-2-pyrazolin-5-one

Downstream raw materials:

3,5-diphenyl-isoxazole-4-carboxylic acid

(+/-)-5endo-hydroxy-2-phenyl-2,6-cyclo-norbornane-3endo-carboxylic acid-lactone

(E)-3-phenylacrylic acid

6-hydroxyflavone

Refernces

• 1、 Gilman,Woods. "-". . p. 520. Retrieved 1945.
• 2、 Finashina,Kustov,Tkachenko,Krasovskiy,Formenova,Beletskaya. "Carboxylation of phenylacetylene by carbon dioxide on heterogeneous Ag-containing catalysts". . p. 2652 - 2656. Retrieved 2014.
• 3、 -. "Method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide". Paragraph 0052-0056; 0055-0057; 0058-0060; 0061-0063; .... . Retrieved 2021/07/24.
• 4、 Bu, Ran,Zhang, Lin,Gao, Lu-Lu,Sun, Weng-Jie,Yang, Shuai-Liang,Gao, En-Qing. "Copper(I)-modified covalent organic framework for CO2 insertion to terminal alkynes". . . Retrieved 2020/12/21.