Pyridine-4-carbaldehyde
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| Names | |
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| Preferred IUPAC name
Pyridine-4-carbaldehyde | |
| Other names
4-formylpyridine, 4-pyridinaldehyde, isonicotinaldehyde | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.011.666 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H5NO | |
| Molar mass | 107.112 g·mol−1 |
| Appearance | colorless liquid |
| Melting point | 4 °C (39 °F; 277 K) |
| Boiling point | 198 °C (388 °F; 471 K) |
| Acidity (pKa) | 4.72 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H317, H319, H335 | |
| P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyridine-4-carbaldehyde is an organic compound with the formula C5H4NCHO. It is one of three isomeric pyridinaldehydes. The other isomers are pyridine-2-carboxaldehyde and pyridine-3-carboxaldehyde. Pyridine-4-carboxaldehyde is a colorless liquid, although aged samples can appear yellow or even brown. It undergoes many reactions expected for aromatic aldehydes such as reductive amination and Schiff base formation.[1] It condenses with pyrrole to give tetrapyridylporphyrin.[2] The pKa has been experimentally determined by NMR spectroscopy to be 4.72.[3]
References
[edit]- ↑ Chougnet, Antoinette; Woggon, Wolf-D. (2013). "Enantioselective Nitroaldol (Henry) Reaction of p-Nitrobenzaldehyde and Nitromethane Using a Copper (II) Complex Derived from (R,R)-1,2-Diaminocyclohexane: (1S)-1-(4-Nitrophenyl)-2-nitroethane-1-ol". Organic Syntheses. 90: 52. doi:10.15227/orgsyn.090.0052.
- ↑ Drain, Charles Michael; Lehn, Jean-Marie (1994). "Self-Assembly of Square Multiporphyrin Arrays by Metal Ion Coordination". Journal of the Chemical Society, Chemical Communications (19): 2313. doi:10.1039/c39940002313.
- ↑ Handloser, Carolyn S.; Chakrabarty, M. R.; Mosher, Melvyn W. (July 1973). "Experimental determination of pKa values by use of NMR chemical shift". Journal of Chemical Education. 50 (7): 510. doi:10.1021/ed050p510. ISSN 0021-9584.