2-Pyrimidinecarboxaldehyde

• CAS: 27427-92-5
• Catalog Number: ACM27427925
• Category: Main Products
• Molecular Weight: 108.1
• Molecular Formula: C5H4N2O
• Melting Point: 40 - 60 °C
• Appearance: Solid

Case Study

2-Pyrimidinecarboxaldehyde as a Key Precursor for Novel Corroles and Porphyrins with 2,6-Pyrimidyl Substituents

Saltsman, Irena, et al. Organic Letters 17.13 (2015): 3214-3217.

2-Pyrimidinecarboxaldehyde serves as a previously unexplored aldehyde for synthesizing corroles and porphyrins bearing 2,6-pyrimidyl groups. Unlike ortho-pyridyl analogs, these macrocycles avoid atropisomerism, while the proximal pyrimidyl nitrogens can influence metal-centered reactivity.
Synthetic Protocol: 2-Pyrimidinecarboxaldehyde was condensed with 5-(2,6-difluorophenyl)dipyrromethane or with 5-(2,6-pyrimidyl)dipyrromethane under Gryko conditions (TFA catalysis, DDQ oxidation) to give A2B corroles 7 and 8. Condensation with pyrrole in 1:4 ratio gave tetra(2,6-pyrimidyl)porphyrin (9). Yields were 8%, 5%, and 12%, respectively. Phosphorus (10) and cobalt (11) complexes of corrole 7 were prepared via POCl3/pyridine and Co(OAc)2/pyridine routes.
Characterization and Performance: X-ray crystallography confirmed near-planar macrocycles with pyrimidyl twist angles of 53-56° relative to the corrole N4 plane-significantly flatter than 2,6-difluorophenyl substituents (64-87°), placing pyrimidyl nitrogens within ~5.5 Å of the metal center. The phosphorus corrole showed extended hydrogen-bonding (OH···O, 2.862 Å) along crystal columns. Cobalt(III) complexes exhibited sharp, resolved ¹H NMR spectra in pyridine, while in noncoordinating solvents they formed paramagnetic Co(II) species (EPR: g1 = 2.450, g2 = 1.999). The porphyrin cobalt complex demonstrated solvent-dependent spin-state switching.
Conclusion: 2-Pyrimidinecarboxaldehyde enables access to a new class of N-heterocyclic macrocycles with fixed geometry, tunable metal coordination, and promising applications in catalysis and sensing.

Custom Q&A

What is the molecular formula of 2-Pyrimidinecarboxaldehyde?

The molecular formula of 2-Pyrimidinecarboxaldehyde is C5H4N2O.

What are the synonyms of 2-Pyrimidinecarboxaldehyde?

The synonyms of 2-Pyrimidinecarboxaldehyde are pyrimidine-2-carbaldehyde and Pyrimidine-2-carboxaldehyde.

What is the molecular weight of 2-Pyrimidinecarboxaldehyde?

The molecular weight of 2-Pyrimidinecarboxaldehyde is 108.10 g/mol.

When was 2-Pyrimidinecarboxaldehyde created?

2-Pyrimidinecarboxaldehyde was created on February 8, 2007.

What is the IUPAC name of 2-Pyrimidinecarboxaldehyde?

The IUPAC name of 2-Pyrimidinecarboxaldehyde is pyrimidine-2-carbaldehyde.

What is the InChI of 2-Pyrimidinecarboxaldehyde?

The InChI of 2-Pyrimidinecarboxaldehyde is InChI=1S/C5H4N2O/c8-4-5-6-2-1-3-7-5/h1-4H.

What is the InChIKey of 2-Pyrimidinecarboxaldehyde?

The InChIKey of 2-Pyrimidinecarboxaldehyde is CCOXWRVWKFVFDG-UHFFFAOYSA-N.

What is the canonical SMILES of 2-Pyrimidinecarboxaldehyde?

The canonical SMILES of 2-Pyrimidinecarboxaldehyde is C1=CN=C(N=C1)C=O.

What is the CAS number of 2-Pyrimidinecarboxaldehyde?

The CAS number of 2-Pyrimidinecarboxaldehyde is 27427-92-5.

What is the European Community (EC) number of 2-Pyrimidinecarboxaldehyde?

The European Community (EC) number of 2-Pyrimidinecarboxaldehyde is 696-076-3.