1H-Pyrazole-3-carbaldehyde

Base Information

• Chemical Name: 1H-Pyrazole-3-carbaldehyde
• CAS No.: 3920-50-1
• Molecular Formula: C4H4N2O
• Molecular Weight: 96.0886
• Hs Code.: 2933199090
• European Community (EC) Number: 630-982-1
• DSSTox Substance ID: DTXSID10959979
• Nikkaji Number: J2.538.963H,J638.207J
• Wikidata: Q72503429
• Mol file: 3920-50-1.mol

Synonyms:1H-Pyrazole-3-carbaldehyde;1H-pyrazole-5-carbaldehyde;3920-50-1;948552-36-1;Pyrazole-3-carboxaldehyde;1H-Pyrazole-5-carboxaldehyde;1H-Pyrazole-3-carboxaldehyde;2H-Pyrazole-3-carbaldehyde;3-Pyrazolecarboxaldehyde;formylpyrazole;209002-03-9;1H-Pyrazole-3-carbaldehyde,dimer;MFCD00129925;1H-Pyrazole-3-carboxaldehyde, dimer (9CI);3-formylpyrazole;Pyrazol-3-carbaldehyde;pyrazole-3-carbaldehyde;1H-Pyrazole-3-carbxaldehyde;pyrazole aldehyde;1H-Pyrazole-3-carbaldehyde, dimer;pyrazole-5-aldehyde;carbonyl-1h-pyrazole;3-formyl-1H-pyrazole;pyrazol-3-carboxaldehyde;PYRAZOLE-5-CARBALDEHYDE;DTXSID10959979;AMY11891;BCP26854;GEO-02174;AKOS005145964;AKOS015854501;AB25611;CS-W004202;GS-5722;1H-Pyrazole-3-carbaldehyde, AldrichCPR;1H-Pyrazole-5-carbaldehyde, AldrichCPR;AC-14384;BL001484;A6568;AM20100032;FT-0647845;P2261;EN300-36665;O10411;A859251;W-200336;Z234896951;1H-pyrazole-5-carbaldehyde pound>>Pyrazole-3-carboxaldehyde

Chemical Property of 1H-Pyrazole-3-carbaldehyde

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 142-144 °C
• Refractive Index: 1.62
• Boiling Point: 299.984 °C at 760 mmHg
• PKA: 11.20±0.10(Predicted)
• Flash Point: 139.672 °C
• PSA: 45.75000
• Density: 1.323 g/cm³
• LogP: 0.22220
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 96.032362755
• Heavy Atom Count: 7
• Complexity: 74.1

Purity/Quality:

99% ^*data from raw suppliers

1-H-Pyrazole-3-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/39

MSDS Files:

Useful:

• Canonical SMILES: C1=C(NN=C1)C=O
• General Description: 2H-Pyrazole-3-carbaldehyde (also known as 3-formylpyrazole or pyrazole-3-carboxaldehyde) is a formyl-substituted pyrazole derivative that serves as a versatile building block in heterocyclic synthesis. In the context of the described copper-catalyzed annulation, it participates as a substrate alongside o-aminoiodoarenes to form pyrrolo[1,2-a]quinoxaline derivatives, demonstrating its utility in constructing biologically relevant heterocycles. The reaction highlights its reactivity at the aldehyde group, enabling efficient cyclization under optimized catalytic conditions.

Technology Process of 1H-Pyrazole-3-carbaldehyde

There total 4 articles about 1H-Pyrazole-3-carbaldehyde 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: 89.0%

pyrazole-3-carboxaldehyde dimethylacetal (111573-59-2,955892-12-3) → 3-formylpyrazole (3920-50-1,209002-03-9)

Guidance literature:

In(OSO₂CF₃)3; In acetone; at 20 ℃; for 8h;

DOI:10.1021/jo0707075

Reference yield:

(1H-pyrazol-3-yl)methanol (23585-49-1) → 3-formylpyrazole (3920-50-1,209002-03-9)

Guidance literature:

With manganese(IV) oxide; In N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/j.bmc.2017.04.004

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + Propargylic aldehyde (624-67-9) → 3-formylpyrazole (3920-50-1,209002-03-9)

Guidance literature:

With diethyl ether;

DOI:10.1093/japr/9.3.424

upstream raw materials:

diazomethane

Propargylic aldehyde

pyrazole-3-carboxaldehyde dimethylacetal

(1H-pyrazol-3-yl)methanol

Downstream raw materials:

2-{4-[6-chloro-2-(1H-pyrazol-3-yl)-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethanol

tert-butyl 3-formyl-1H-pyrazole-1-carboxylate

1-allyl-1H-pyrazole-3-carbaldehyde

1-benzyl-1H-pyrazole-3-carbaldehyde

Refernces

Copper-catalyzed annulation of 2-formylazoles with o-aminoiodoarenes

10.1021/jo9025644

The research focuses on the development of a copper-catalyzed annulation reaction between 2-formylazoles and o-aminoiodoarenes, leading to the synthesis of substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. This method provides a one-step route to these biologically active molecules, which are present in a growing number of pharmaceutical compounds. The reaction conditions were optimized using 2-iodoaniline and 2-formylpyrrole as starting materials, with the best results obtained using 1 equivalent of 2-formylpyrrole, 1.5 equivalents of 2-iodoaniline, 2 equivalents of K3PO4, 10 mol % CuI, 20 mol % sparteine, and NMP as the solvent at 130°C for 24 hours. The reaction was found to be effective for a variety of substituted aminoiodoarenes and formylazoles, including 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole. The synthesized products were analyzed using techniques such as high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS) to confirm their structures and purities.