succinaldehyde
{{Chembox
| ImageFile = Succindialdehyde.svg
| PIN = Butanedial{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |page=908 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}
| OtherNames = Succinaldehyde
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 638-37-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0503177591
| PubChem = 12524
| ChemSpiderID = 12007
| SMILES = O=CCCC=O
| InChI = 1S/C4H6O2/c5-3-1-2-4-6/h3-4H,1-2H2
}}
|Section2={{Chembox Properties
| Formula = C4H6O2
| MolarMass = 86.09
| Appearance = colourless liquid
| Density = 1.064 g/cm3
| MeltingPt =
| BoilingPtC = 58
| BoilingPt_notes = at 9 mm Hg
| Solubility = with hydration
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Succinaldehyde or Butanedial is an organic compound with the formula {{chem2|(C2H4(CHO)2}}. It is a colorless viscous liquid. Typical of some other saturated dialdehydes, succinaldehyde is handled as the hydrates or methanol-derived acetal. It is a precursor to tropinone.{{US patent|2710883}} Succinaldehyde can be used as a crosslinking agent for proteins, but it is less widely used than the related dialdehyde glutaraldehyde.
Preparation and reactions
File:SuccinaldehydeHydrate.png
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.{{cite journal |doi=10.15227/orgsyn.099.0139 |title=Organocatalytic Dimerization of Succinaldehyde |date=2022 |last1=Bennett |first1=Steven H. |first2=Varinder K.|last2=Aggarwal|journal=Organic Syntheses |volume=99 |pages=139–158 }}
In the presence of water, succinaldehyde converts to the cyclic hydrate.{{cite journal|doi=10.1039/P29720002270|title=The Hydration and Polymerisation of Succinaldehyde, Glutaraldehyde, and Adipaldehyde|year=1972|last1=Hardy|first1=P. M.|last2=Nicholls|first2=A. C.|last3=Rydon|first3=H. N.|journal=Journal of the Chemical Society, Perkin Transactions 2|issue=15|page=2270}} In methanol it converts to the cyclic acetal, 2,5-dimethoxyltetrahydrofuran.{{Ullmann|author=Christian Kohlpaintner |author2=Markus Schulte |author3=Jürgen Falbe |author4=Peter Lappe |author5=Jürgen Weber |title=Aldehydes, Aliphatic|year=2008|doi= 10.1002/14356007.a01_321.pub2}}
References
{{Reflist}}