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Pyridine-4-carbaldehyde

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Pyridine-4-carbaldehyde
Names
Preferred IUPAC name Pyridine-4-carbaldehyde
Other names 4-formylpyridine, 4-pyridinaldehyde, isonicotinaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.666 Edit this at Wikidata
EC Number
  • 212-832-3
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5NO/c8-5-6-1-3-7-4-2-6/h1-5HKey: BGUWFUQJCDRPTL-UHFFFAOYSA-N
SMILES
  • C1=CN=CC=C1C=O
Properties
Chemical formula C6H5NO
Molar mass 107.112 g·mol
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:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H317, H319, H335
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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. It condenses with pyrrole to give tetrapyridylporphyrin. The pKa has been experimentally determined by NMR spectroscopy to be 4.72.

References

  1. 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.
  2. 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.
  3. 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.
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