Pyridine-3-carbaldehyde

Pyridine-3-carbaldehyde, also known as nicotinaldehyde, is an organic compound with the formula C5H4NCHO. It is one of three isomeric pyridinaldehydes. The other isomers are pyridine-2-carboxaldehyde and pyridine-4-carboxaldehyde. It is a colorless liquid that is routinely available commercially. It can be produced from nicotinonitrile. Alternatively, it arises by the aerobic oxidation of the corresponding alcohol.[1]

Pyridine-3-carbaldehyde
Names
Preferred IUPAC name
Pyridine-3-carbaldehyde
Other names
Nicotinaldehyde, 3-formylpyridine, 3-pyridinaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.183 Edit this at Wikidata
EC Number
  • 207-900-4
KEGG
UNII
  • InChI=1S/C6H5NO/c8-5-6-2-1-3-7-4-6/h1-5H
    Key: QJZUKDFHGGYHMC-UHFFFAOYSA-N
  • C1=CC(=CN=C1)C=O
Properties
C6H5NO
Molar mass 107.112 g·mol−1
Appearance colorless liquid
Density 1.14 g/cm3
Melting point 7 °C (45 °F; 280 K)
Boiling point 95–97 °C (203–207 °F; 368–370 K) 15 mm
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H302, H315, H317, H318, H334, H335, H341, H412
P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P273, P280, P281, P285, P301+P312, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P333+P313, P342+P311, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Safety

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3-Pyridinecarboxaldehyde is a severe skin irritant.[2]

References

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  1. ^ Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. (1996). "Copper-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones: An Efficient, Aerobic Alternative". Science. 274 (5295): 2044–2046. Bibcode:1996Sci...274.2044M. doi:10.1126/science.274.5295.2044. PMID 8953027. S2CID 23952453.
  2. ^ H. Stetter1, H. Kuhlmann, and G. Lorenz (1979). "Cyanide-Catalyzed Conjugate Addition of Aryl Aldehydes: 4-Oxo-4-(3-Pyridyl)Butyronitrile". Organic Syntheses. 59: 53. doi:10.15227/orgsyn.059.0053.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)