2-Pyridinecarboxaldehyde

2-Pyridinecarboxaldehyde Basic information
Product Name:2-Pyridinecarboxaldehyde
Synonyms:AKOS BBS-00003192;2-FORMYLPYRIDINE;2-PA;2-PICOLINIC ALDEHYDE;2-PYRIDINECARBALDEHYDE;2-PYRIDINECARBOXALDEHYDE;TIMTEC-BB SBB004358;PYRIDINE-2-CARBOXALDEHYDE
CAS:1121-60-4
MF:C6H5NO
MW:107.11
EINECS:214-333-6
Product Categories:Heterocycle-Pyridine series;Building Blocks;C1 to C6;C6;Carbonyl Compounds;Chemical Synthesis;Pyridine series;Aldehydes;Pyridines;Pyridines derivates;Heterocyclic Compounds;Heterocyclic Building Blocks;Organic Building Blocks;pharm intermediate;Pyridine;bc0001;1121-60-4
Mol File:1121-60-4.mol
2-Pyridinecarboxaldehyde Structure
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)
pka3.8(at 20℃)
color Clear yellow to yellow-brown
PH6.5 (111g/l, H2O, 20℃)
Water Solubility miscible
Sensitive Air Sensitive
BRN 105341
InChIKeyCSDSSGBPEUDDEE-UHFFFAOYSA-N
LogP0.714 at 20.5℃
CAS DataBase Reference1121-60-4(CAS DataBase Reference)
NIST Chemistry Reference2-Pyridinecarboxaldehyde(1121-60-4)
EPA Substance Registry System2-Pyridinecarboxaldehyde (1121-60-4)
Safety Information
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
8-10-23
Hazard Note Irritant/Keep Cold/Air Sensitive
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29333999
MSDS Information
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2-Pyridinecarboxaldehyde English
SigmaAldrich English
ACROS English
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2-Pyridinecarboxaldehyde Usage And Synthesis
Chemical PropertiesYellow liquid
Uses2-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.
DefinitionChEBI: 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 MethodsPurification 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-Hydrazinopyridine Di-2-pyridylglyoxal 2,6-Pyridinedicarboxylic acid chloride DI-2-PYRIDYL KETONE Pyridine-2,6-dicarboxylic acid 2,3-Pyridinedicarboxylic acid FUSARIC ACID 2,6-Diacetylpyridine 2,3-Pyridinedicarboxylic anhydride 2,5-PYRIDINEDICARBOXYLIC ACID Ethyl picolinate 3-HYDROXYPICOLINAMIDE 2-Acetylpyridine Quinaldic acid 2,4-Pyridinedicarboxylic acid 1-Tetradecanol PICOLINIC ACID N-OXIDE 2-Benzoylpyridine

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