Adipaldehyde

Adipaldehyde
Names
	IUPAC name hexanedial
	Other names 1,4-Butane dicarboxaldehyde, 1,6-hexanedial
Identifiers
CAS Number	1072-21-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:180386;
ChemSpider	63788;
ECHA InfoCard	100.012.731
EC Number	214-003-1;
PubChem CID	70620;
UNII	6W2N7U6ZHE;
CompTox Dashboard (EPA)	DTXSID10147935 ;
	InChI InChI=1S/C6H10O2/c7-5-3-1-2-4-6-8/h5-6H,1-4H2 Key: UMHJEEQLYBKSAN-UHFFFAOYSA-N;
	SMILES C(CCC=O)CC=O;
Properties
Chemical formula	C6H10O2
Molar mass	114.144 g·mol−1
Appearance	colorless liquid
Density	1.003 g/cm3
Melting point	−8 °C (18 °F; 265 K)
Boiling point	68–70 °C (154–158 °F; 341–343 K) 3 mm Hg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Adipaldehyde is the organic compound with the formula (CH₂)₄(CHO)₂. It is a colorless oil that is usually encountered as an aqueous solution because it is highly reactive like many dialdehydes.^[1] The compound has attracted interest as a precursor to nylon-related polymers. It can be produced by double hydroformylation of 1,3-butadiene, but this methodology has not achieved commercialization.^[2] It has been prepared by oxidation of 1,6-hexanediol with pyridinium chlorochromate.^[3]

References

^ 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.
^ Yu, Si-min; Snavely, William K.; Chaudhari, Raghunath V.; Subramaniam, Bala (2020). "Butadiene hydroformylation to adipaldehyde with Rh-based catalysts: Insights into ligand effects". Molecular Catalysis. 484. doi:10.1016/j.mcat.2019.110721. S2CID 213312335.
^ Corey, E.J.; Suggs, J.William (1975). "Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds". Tetrahedron Letters. 16 (31): 2647–2650. doi:10.1016/s0040-4039(00)75204-x.

[1] 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.

[2] Yu, Si-min; Snavely, William K.; Chaudhari, Raghunath V.; Subramaniam, Bala (2020). "Butadiene hydroformylation to adipaldehyde with Rh-based catalysts: Insights into ligand effects". Molecular Catalysis. 484. doi:10.1016/j.mcat.2019.110721. S2CID 213312335.

[3] Corey, E.J.; Suggs, J.William (1975). "Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds". Tetrahedron Letters. 16 (31): 2647–2650. doi:10.1016/s0040-4039(00)75204-x.

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