2-Hydroxy-3-phenylprop-2-enoic acid

Base Information

• Chemical Name: 2-Hydroxy-3-phenylprop-2-enoic acid
• CAS No.: 5801-57-0
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• DSSTox Substance ID: DTXSID701295081
• Wikidata: Q27104236
• Mol file: 5801-57-0.mol

Synonyms:enol-Phenylpyruvic acid;2-hydroxy-3-phenylprop-2-enoic acid;Cinnamic acid, ar-hydroxy-;SCHEMBL141612;CHEBI:32815;2-Hydroxy-3-phenyl-acrylic acid;DTXSID701295081;2-Hydroxy-3-phenyl-2-propenoic acid;Q27104236

Chemical Property of 2-Hydroxy-3-phenylprop-2-enoic acid

Chemical Property:

• Vapor Pressure: 2.64E-05mmHg at 25°C
• Boiling Point: 343.7°C at 760 mmHg
• Flash Point: 175.9°C
• Density: 1.341g/cm³
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C(C(=O)O)O

Technology Process of 2-Hydroxy-3-phenylprop-2-enoic acid

There total 21 articles about 2-Hydroxy-3-phenylprop-2-enoic 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: 95.0%

1-acetyl-3-[(Z)-benzylidene]-2,5-piperazinedione (30166-29-1,30166-30-4,41808-11-1) → (Z)-2-hydroxy-3-phenyl-acrylic acid (5801-57-0,52178-60-6)

Guidance literature:

With hydrogenchloride; water; for 4h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2012.06.078

Reference yield: 85.0%

(E)-5-benzylidene-2,2-dimethyl-1,3-oxazolidin-4-one → (Z)-2-hydroxy-3-phenyl-acrylic acid (5801-57-0,52178-60-6)

Guidance literature:

With hydrogenchloride; water; for 0.25h; Reflux;

DOI:10.1134/S1070363217120088

Reference yield: 80.0%

allylbenzene (300-57-2,57807-91-7) → (Z)-2-hydroxy-3-phenyl-acrylic acid (5801-57-0,52178-60-6)

Guidance literature:

With tert.-butylhydroperoxide; water; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 90 ℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Green chemistry;

DOI:10.1021/acs.orglett.1c02021

upstream raw materials:

4-benzylidene-2-methyl-2-oxazolin-5-one

benzaldehyde

(4E)-2-methyl-4-(phenylmethylidene)-4,5-dihydro-1,3-oxazol-5-one

5-benzylidenehydantoin

Downstream raw materials:

methyl-2-hydroxy-3-phenylacrylate

3-phenylpropane-1,2-diol

methyl 2-hydroxy-3-phenylpropanoate

trans-4,6,7-trihydroxy-1-benzyl-1,2,3,4-tetrahydroisoqinoline-1-carboxylic acid

Refernces

• 1、 Song, Tao,Ma, Zhiming,Wang, Xiaoxue,Yang, Yong. "Synthesis of α-Keto Acids via Oxidation of Alkenes Catalyzed by a Bifunctional Iron Nanocomposite". supporting information. p. 5917 - 5921. Retrieved 2021/07/31.
• 2、 Wang,Zhao,Que. "Synthesis of the Natural Product Iotrochamide B". . p. 499 - 501. Retrieved 2019/07/02.