Glutaconaldehyde

Glutaconaldehyde is an organic compound with the formula C₅H₆O₂. It is an unsaturated dialdehyde as is related to glutaraldehyde and glutaconic acid, but exists in its enol form due to the conjugation with the double bond.

Glutaconaldehyde

Names
Preferred IUPAC name (2E,4E)-5-Hydroxypenta-2,4-dienal
Other names Glutacondialdehyde; Glutaconic aldehyde; Glutaconic dialdehyde; Pentenedial
Identifiers
CAS Number	821-42-1 Y
3D model (JSmol)	Interactive image
ChemSpider	4779496 Y
PubChem CID	6011936
InChI InChI=1S/C5H6O2/c6-4-2-1-3-5-7/h1-6H/b3-1+,4-2+ Y Key: WFSXUTWNNVIIIG-ZPUQHVIOSA-N Y InChI=1/C5H6O2/c6-4-2-1-3-5-7/h1-6H/b3-1+,4-2+ Key: WFSXUTWNNVIIIG-ZPUQHVIOBI
SMILES O=C\C=C\C=C\O
Properties
Chemical formula	C5H6O2
Molar mass	98.101 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Both the sodium and potassium salts of glutaconaldehyde are known. They are efficiently synthesized from pyridinium sulfonate.^[1][2]

The reaction of the glutaconaldehyde anion with acid chlorides gives the corresponding enol esters.^[1] Glutaconaldehyde can also be converted to the corresponding vinyl bromide as shown below.^[3] This product can be reacted with nucleophiles, cross-coupled using palladium, or homologated by two carbons.^[3][4]

References

1. Baumgarten, P. (1924). "Über den Abbau des Pyridins zu Glutaconsäuredialdehyd und dessen Rückverwandlung in Pyridin (I.)". Ber. Dtsch. Chem. Ges. 57 (8): 1622–1627. doi:10.1002/cber.19240570876.
2. Becher, J. (1979). "Glutaconaldehyde Sodium Salt from Hydrolysis of Pyridinium-1-Sulfonate". Organic Syntheses. 59: 79–84. doi:10.15227/orgsyn.059.0079.
3. Soullez, D.; Ple, G.; Duhamel, L. Duhamel P. (1995). "5-Bromopentadienal: A Versatile Intermediate for the Synthesis of Functionalized Polyenic Compounds". J. Chem. Soc., Chem. Commun. (5): 563–564. doi:10.1039/C39950000563.
4. Vicart, N.; Castet-Caillabet, D.; Ramondenc, Y.; Ple, G.; Duhamel, L. (1998). "Application of (2E,4E)-5-Bromo-2,4-Pentadienal in Palladium Catalysed Cross-Coupling: Easy Access to (2E,4E)-2,4-Dienals". Synlett (4): 411–412. doi:10.1055/s-1998-1672.