Succinaldehyde

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Succinaldehyde
Succindialdehyde.svg
Names
Preferred IUPAC name
Butanedial [1]
Other names
Succinaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.304 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C4H6O2/c5-3-1-2-4-6/h3-4H,1-2H2
  • O=CCCC=O
Properties
C4H6O2
Molar mass 86.09
Appearancecolourless liquid
Density 1.064 g/cm3
Boiling point 58 °C (136 °F; 331 K) at 9 mm Hg
with hydration
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. SuccinaldehydeHydrate.png
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]

Related Research Articles

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2
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2
is for dry-cell batteries, such as the alkaline battery and the zinc–carbon battery. MnO
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is also used as a pigment and as a precursor to other manganese compounds, such as KMnO
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4
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. In this regard it is comparable to the tellurate ion from the adjacent group. It can combine with a number of counter ions to form periodates, which may also be regarded as the salts of periodic acid.

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References

  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.
  2. 1 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.