Succinaldehyde

Succinaldehyde
Names
	Preferred IUPAC name Butanedial
	Other names Succinaldehyde
Identifiers
CAS Number	638-37-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	12007;
ECHA InfoCard	100.010.304
PubChem CID	12524;
UNII	0503177591 ;
CompTox Dashboard (EPA)	DTXSID3021514 ;
	InChI InChI=1S/C4H6O2/c5-3-1-2-4-6/h3-4H,1-2H2;
	SMILES O=CCCC=O;
Properties
Chemical formula	C4H6O2
Molar mass	86.09
Appearance	colourless liquid
Density	1.064 g/cm3
Boiling point	58 °C (136 °F; 331 K) at 9 mm Hg
Solubility in water	with hydration
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Succinaldehyde or succindialdehyde is an organic compound with the formula (C₂H₄(CHO)₂. It is a colorless viscous liquid.^[2] Typical of some other saturated dialdehydes, succinaldehyde is handled as the hydrates or methanol-derived acetal. It is a precursor to tropinone.^[3] Succinaldehyde can be used as a crosslinking agent for proteins, but it is less widely used than the related dialdehyde glutaraldehyde.

Preparation and reactions

2,5-Dihydroxytetrahydrofuran, the hydrated form of succinaldehyde.

Succinaldehyde is generated by the oxidation of tetrahydrofuran with chlorine followed by hydrolysis of the chlorinated product. It can also be prepared by the hydroformylation of acrolein or the acetals thereof. Oxidation of 2,5-dimethoxytetrahydrofuran with hydrogen peroxide is yet another route to succinaldehyde.^[2]

In the presence of water, succinaldehyde converts to the cyclic hydrate.^[4] In methanol it converts to the cyclic acetal, 2,5-dimethoxyltetrahydrofuran.^[5]

References

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 908. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ ^a ^b Bennett, Steven H.; Aggarwal, Varinder K. (2022). "Organocatalytic Dimerization of Succinaldehyde". Organic Syntheses. 99: 139–158. doi:10.15227/orgsyn.099.0139.
^ U.S. patent 2,710,883
^ Hardy, P. M.; Nicholls, A. C.; Rydon, H. N. (1972). "The Hydration and Polymerisation of Succinaldehyde, Glutaraldehyde, and Adipaldehyde". Journal of the Chemical Society, Perkin Transactions 2 (15): 2270. doi:10.1039/P29720002270.
^ Christian Kohlpaintner; Markus Schulte; Jürgen Falbe; Peter Lappe; Jürgen Weber (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3527306732.

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 908. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[OS-2] Bennett, Steven H.; Aggarwal, Varinder K. (2022). "Organocatalytic Dimerization of Succinaldehyde". Organic Syntheses. 99: 139–158. doi:10.15227/orgsyn.099.0139.

[3] U.S. patent 2,710,883

[4] Hardy, P. M.; Nicholls, A. C.; Rydon, H. N. (1972). "The Hydration and Polymerisation of Succinaldehyde, Glutaraldehyde, and Adipaldehyde". Journal of the Chemical Society, Perkin Transactions 2 (15): 2270. doi:10.1039/P29720002270.

[5] Christian Kohlpaintner; Markus Schulte; Jürgen Falbe; Peter Lappe; Jürgen Weber (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3527306732.

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