(2Z)-2-benzylidene-3-methyl-3,4-dihydropyrazol-2-ium-5-olate

Base Information

• Chemical Name: (2Z)-2-benzylidene-3-methyl-3,4-dihydropyrazol-2-ium-5-olate
• CAS No.: 14893-83-5
• Molecular Formula: C11H12 N2 O
• Molecular Weight: 188.229
• NSC Number: 140266
• DSSTox Substance ID: DTXSID00421231
• Mol file: 14893-83-5.mol

Synonyms:14893-83-5;AC1NYBHI;DTXSID00421231;NSC140266;NSC-140266

Chemical Property of (2Z)-2-benzylidene-3-methyl-3,4-dihydropyrazol-2-ium-5-olate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 188.094963011
• Heavy Atom Count: 14
• Complexity: 265

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=N[N+]1=CC2=CC=CC=C2)[O-]
• Isomeric SMILES: CC\1CC(=N/[N+]1=C\C2=CC=CC=C2)[O-]

Technology Process of (2Z)-2-benzylidene-3-methyl-3,4-dihydropyrazol-2-ium-5-olate

There total 4 articles about (2Z)-2-benzylidene-3-methyl-3,4-dihydropyrazol-2-ium-5-olate 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: 83.0%

5-methyl-pyrazolidin-3-one (10234-76-1) + benzaldehyde (100-52-7) → 1-benzylidene-5-methyl-4,5-dihydro-3H-1λ5-pyrazol-3-one (14893-83-5)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; Heating;

Reference yield: 75.0%

methyl crotonate (623-43-8,4358-59-2,18707-60-3,130981-57-6) + benzaldehyde (100-52-7) → 1-benzylidene-5-methyl-4,5-dihydro-3H-1λ5-pyrazol-3-one (14893-83-5)

Guidance literature:

methyl crotonate; With hydrazine hydrate; In ethanol; at 78 ℃; for 1h;

benzaldehyde; In methanol;

DOI:10.1021/acs.orglett.6b01104

Reference yield:

ethyl crotonate (10544-63-5) + benzaldehyde (100-52-7) → 1-benzylidene-5-methyl-4,5-dihydro-3H-1λ5-pyrazol-3-one (14893-83-5)

Guidance literature:

ethyl crotonate; With hydrazine hydrate;

benzaldehyde;

DOI:10.1016/j.tet.2015.10.022

upstream raw materials:

5-methyl-pyrazolidin-3-one

benzaldehyde

methyl crotonate

ethyl crotonate

Downstream raw materials:

ethyl 7-methyl-5-oxo-1-phenyl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylate

Refernces

• 1、 Matsuo, Bianca T.,Correia, José Tiago M.,Paix?o, Márcio W.. "Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones". supporting information. p. 7891 - 7896. Retrieved 2020/11/02.
• 2、 Dürüst, Yaar,Sairli, Eda,Sairli, Akin. "Microwave-assisted regioselective [1,3]-dipolar cycloaddition of 3-methyl-2-(substitutedbenzylidene)-5-oxopyrazolidin-2-ium-1-ides to benzothiophene 1,1-dioxide". . p. 789 - 800. Retrieved 2015/08/06.