Pyridine-4-carbaldehyde

Pyridine-4-carbaldehyde
Names
	Preferred IUPAC name Pyridine-4-carbaldehyde
	Other names 4-formylpyridine, 4-pyridinaldehyde, isonicotinaldehyde
Identifiers
CAS Number	872-85-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2251606;
ChemSpider	12816;
ECHA InfoCard	100.011.666
EC Number	212-832-3;
PubChem CID	13389;
UNII	P577557492 ;
CompTox Dashboard (EPA)	DTXSID1061237 ;
	InChI InChI=1S/C6H5NO/c8-5-6-1-3-7-4-2-6/h1-5H Key: BGUWFUQJCDRPTL-UHFFFAOYSA-N;
	SMILES C1=CN=CC=C1C=O;
Properties
Chemical formula	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:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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

^ 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.

[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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