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Succinaldehyde

Succinaldehyde

Succinaldehyde or Butanedial is an organic compound with the formula . It is a colorless viscous liquid. 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.

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

References

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. Typical of some other saturated [[dialdehyde]]s, succinaldehyde is handled as the hydrates or methanol-derived [[acetal]]. It is a precursor to [[tropinone]].{{US patent. 2710883
  3. (2022). "Organocatalytic Dimerization of Succinaldehyde". Organic Syntheses.
  4. (1972). "The Hydration and Polymerisation of Succinaldehyde, Glutaraldehyde, and Adipaldehyde". Journal of the Chemical Society, Perkin Transactions 2.
  5. Christian Kohlpaintner. (2008). "Aldehydes, Aliphatic".
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