Succinaldehyde
Appearance
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Names | |
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Preferred IUPAC name
Butanedial | |
Other names
Succinaldehyde
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.010.304 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
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 |
with hydration | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Succinaldehyde or succindialdehyde is an organic compound with the formula (CH2CHO)2. Typical of other dialdehydes, succinaldehyde is highly reactive. Usually, it is handled as the hydrates or methanol-derived acetal. It is a precursor to tropinone.[1] It is used as a crosslinking agent but is less widely used than the related dialdehyde glutaraldehyde.
Preparation
![](http://upload.wikimedia.org/wikipedia/commons/thumb/0/0a/SuccinaldehydeHydrate.png/220px-SuccinaldehydeHydrate.png)
Succinaldehyde is generated by the oxidation of THF with chlorine followed by hydrolysis and by the hydroformylation of acrolein derivatives.
In aqueous solution, the molecule hydrates and cyclizes.[2] In methanol it converts to the cyclic acetal, 2,5-dimethoxyltetrahydrofuran.[3]
References
- ^ 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.
- ^ "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2008. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3527306732.
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