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| | 2-Pyridinecarboxaldehyde Basic information | | Synthesis |
| | 2-Pyridinecarboxaldehyde Chemical Properties |
| Melting point | -21--22°C | | Boiling point | 181 °C(lit.) | | density | 1.126 g/mL at 25 °C(lit.) | | vapor pressure | 73Pa at 20℃ | | refractive index | n20/D 1.536(lit.) | | Fp | 130 °F | | storage temp. | 2-8°C | | form | liquid (strong colored) | | pka | 3.8(at 20℃) | | color | Clear yellow to yellow-brown | | PH | 6.5 (111g/l, H2O, 20℃) | | Water Solubility | miscible | | Sensitive | Air Sensitive | | BRN | 105341 | | InChI | 1S/C6H5NO/c8-5-6-3-1-2-4-7-6/h1-5H | | InChIKey | CSDSSGBPEUDDEE-UHFFFAOYSA-N | | SMILES | [H]C(=O)c1ccccn1 | | LogP | 0.714 at 20.5℃ | | CAS DataBase Reference | 1121-60-4(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Pyridinecarboxaldehyde(1121-60-4) | | EPA Substance Registry System | 2-Pyridinecarboxaldehyde (1121-60-4) |
| Hazard Codes | Xn,Xi,N,T,F | | Risk Statements | 10-22-36/37/38-51/53-46-43-34-23-52 | | Safety Statements | 7-26-36-61-53-45-36/37/39-29-16-36/37 | | RIDADR | UN 1989 3/PG 3 | | WGK Germany | 3 | | F | 8-10-23 | | Hazard Note | Irritant/Keep Cold/Air Sensitive | | TSCA | TSCA listed | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29333999 | | Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | | Hazard Classifications | Acute Tox. 2 Inhalation
Acute Tox. 4 Oral
Eye Dam. 1
Skin Corr. 1B
Skin Sens. 1 |
| | 2-Pyridinecarboxaldehyde Usage And Synthesis |
| Synthesis | DMF (5 mL), mesitylene (0.25 mL, 1.8 x 10⁻³ mol), and Et₃SiH (1.166 mL, 7.2 x 10⁻³ mol) were added to 4-bromotoluene (0.616 g, 3.6 × 10⁻³ mol), [PdCl₂(dppp)] (0.053 g, 9 x 10⁻⁵ mol), and Na₂CO₃ (0.381 g, 3.6 × 10⁻³ mol) as references. Once sealed in the reactor, the system was purged several times with CO. The temperature was raised to 90 °C, and 3 bar of CO was added to the reactor. The reaction was stirred under these conditions for 18 hours, and then the reactor was allowed to cool. The reactants were filtered, and the filtrate was analyzed by GC-MS to determine the conversion and yield of the aldehyde. The final structure was confirmed to yield the title compound, pyridine-2-carboxaldehyde.
 Figure: Synthetic Route of 2-Pyridinecarboxaldehyde | | Chemical Properties | Yellow liquid | | Uses | 2-Pyridinecarboxaldehyde has been used:
- To synthesize chitosan based bifunctionalized adsorbent.
- In the aldol addition reaction with pyruvate in the presence of 2-keto-3-deoxy-6-phosphogluconate aldolase (KDPG) catalyst to form (S)-4-hydroxy-2-keto-4-(2′-pyridyl)butyrate.
- In the condensation reaction with (S)-()-α-methylbenzylamine and (R)-(+)-α-methylbenzylamine to synthesize two chiral (S)-()- and (R)-(+)Schiff base compounds.
It can also be combined with thiosemicarbazide to form 2-pyridinecarboxaldehyde thiosemicarbazone ligand (L) which can further complex with Ni(II) and Cu(II) salts (MX) to form [M(L)2X2] complexes. | | Definition | ChEBI: 2-Pyridinecarboxaldehyde is a pyridinecarbaldehyde that is pyridine in which the hydrogen at position 2 is replaced by a formyl group. | | Synthesis Reference(s) | Synthetic Communications, 23, p. 1775, 1993 DOI: 10.1080/00397919308011276 | | Purification Methods | Purification is achieved by bubbling sulfur dioxide into a solution of 50g of the aldehyde in 250mL of boiled water, under nitrogen, at 0o, until precipitation is complete. The bisulfite addition compound is filtered off rapidly and, after washing with a little water, is refluxed in 17% HCl (200mL) under nitrogen until a clear solution is obtained. Neutralisation with NaHCO3 and extraction with ether separated the aldehyde which is recovered by drying the extract, then distilling twice, under nitrogen. [Kyte et al. J Chem Soc 4454 1960, Beilstein 21 I 287, 21 III/IV 3495, 21/7 V 293.] |
| | 2-Pyridinecarboxaldehyde Preparation Products And Raw materials |
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