(2E)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-enoic acid

Base Information

• Chemical Name: (2E)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-enoic acid
• CAS No.: 27268-04-8
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.224
• DSSTox Substance ID: DTXSID201331094
• Nikkaji Number: J481.784B
• ChEMBL ID: CHEMBL1388351
• Mol file: 27268-04-8.mol

Synonyms:(2E)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-enoic acid;27268-04-8;(E)-3-(1-phenylpyrazol-4-yl)prop-2-enoic Acid;3-(1-phenyl-1H-pyrazol-4-yl)prop-2-enoic acid;MLS000760877;CHEMBL1388351;DTXSID201331094;HMS1741J08;HMS2707M05;CBA26804;AKOS000263689;AKOS025149126;SMR000372186;EN300-14664;EN300-34469;AB00617842-02;(E)-3-(1-Phenyl-1H-pyrazol-4-yl)propenoic acid;(2E)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-enoicacid;Z2895086384

Chemical Property of (2E)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-enoic acid

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.074227566
• Heavy Atom Count: 16
• Complexity: 272

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C=C(C=N2)C=CC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)N2C=C(C=N2)/C=C/C(=O)O

Technology Process of (2E)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-enoic acid

There total 10 articles about (2E)-3-(1-phenyl-1H-pyrazol-4-yl)prop-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: 90.0%

1-phenyl-1H-pyrazole-4-carbaldehyde (54605-72-0) + malonic acid (141-82-2) → (E)-3-(1-phenylpyrazol-4-yl)prop-2-enoic acid (27268-04-8)

Guidance literature:

With piperidine; pyridine; at 115 ℃; for 4h;

DOI:10.1002/jhet.5570290220

Reference yield:

3-[(E)-(2-phenylhydrazinylidene)methyl]pyridine (57023-37-7) → (E)-3-(1-phenylpyrazol-4-yl)prop-2-enoic acid (27268-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / acetone / 2 h / Heating

2: 70 percent / 10percent aq. NaOH / CH₂Cl₂; H₂O / 20 h / Ambient temperature

3: 0.55 g / AgNO₃, 0.5N NaOH / ethanol; H₂O / Ambient temperature

With sodium hydroxide; silver nitrate; In ethanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.28.1265

Reference yield:

1-Methyl-3-(phenyl-hydrazonomethyl)-pyridinium; iodide (60441-21-6) → (E)-3-(1-phenylpyrazol-4-yl)prop-2-enoic acid (27268-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / 10percent aq. NaOH / CH₂Cl₂; H₂O / 20 h / Ambient temperature

2: 0.55 g / AgNO₃, 0.5N NaOH / ethanol; H₂O / Ambient temperature

With sodium hydroxide; silver nitrate; In ethanol; dichloromethane; water;

DOI:10.1248/cpb.28.1265

upstream raw materials:

1-phenyl-1H-pyrazole-4-carbaldehyde

malonic acid

2-((1-phenyl-1H-pyrazol-4-yl)methylene)malonic acid

3-(1-phenylpyrazol-4-yl)acrylaldehyde

Downstream raw materials:

2-bromo-3-(1-phenyl-1H-pyrazol-4-yl)-acrylic acid ethyl ester

3-oxo-3-(1-phenyl-1H-pyrazol-4-yl)-propionic acid

1-(1-phenyl-1H-pyrazol-4-yl)ethan-1-one

4-(4-bromo-styryl)-1-phenyl-1H-pyrazole

Refernces

• 1、 Tanaka,Wachi,Terada. "Formation of pyrazole derivatives from β-substituted pyridinium salts". . p. 1265 - 1269. Retrieved 2007/10/02.