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

EC Number |

* 212-832-3

PubChem CID

* 13389

UNII |

* P577557492 Y

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 pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H317, H319, H335

GHS precautionary statements

| P261, P264, P271, P272, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P333+313, P337+313, P362, P363, P403+233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

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

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" (in en). Journal of Chemical Education 50 (7): 510. doi:10.1021/ed050p510. ISSN 0021-9584. https://pubs.acs.org/doi/abs/10.1021/ed050p510.

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*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H317]: May cause an allergic skin reaction
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P333+313]: If skin irritation or a rash occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P363]: Wash contaminated clothing before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …