630-19-3

Clear colorless liquid

Commonly used building block in aldol condensation reactions.

Pivaldehyde is a hazardous by-product released from engine exhaust and is often used as a raw material for organic synthesis or as a reagent in chemical reactions. It can be copolymerised with aldehyde anions, such as acrolein, to prepare unsaturated polyacetals, or a TBPB initiated decarbonylative cascade cyclization of ortho-cyanoarylacrylamides with pivaldehyde leads to tert-butyl containing quinolone-2,4(1H,3H)-diones by formation of both C(sp³)–C(sp³) and C(s^p3)–C(sp²) bonds. As well as probing the absolute rate constants of its autoxidation, etc^[1-3].

ChEBI: 2,2-dimethylpropanal is a member of the class of propanals that is propanal substituted by two methyl groups at position 2. It is a member of propanals and a 2-methyl-branched fatty aldehyde.

[1] A. LAPENA R. S J L Mateo. Anionic copolymerization of acrolein with aldehydes. III[J]. Journal of Polymer Science: Polymer Symposia, 1973, 42 1: 311-319. DOI:10.1002/polc.5070420133.
[2] CUI ZHANG. Decarbonylative cascade cyclization of ortho-cyanoarylacrylamides with pivaldehyde: Access to tert-butyl containing quinolone-2,4(1H,3H)-diones[J]. Tetrahedron, 2022. DOI:10.1016/j.tet.2021.132547.
[3] G. ZAIKOV K. I J Howard. Absolute rate constants for hydrocarbon autoxidation. XIII. Aldehydes: photo-oxidation, co-oxidation, and inhibition[J]. Canadian Journal of Chemistry, 1969. DOI:10.1139/V69-500.
[4] Ho, Tse Lok, et al. Pivaldehyde. Fieser and Fieser's Reagents for Organic Synthesis. John Wiley & Sons, Inc. 2006.
[5] https://en.wikipedia.org/wiki/Acetaldehyde#Uses
[6] https://en.wikipedia.org/wiki/Pivaldehyde
[7] https://www.alfa.com/en/catalog/A15013/
[8] GEORGE A. OLAH. Acid-Catalyzed Isomerization of Pivalaldehyde to Methyl Isopropyl Ketone via a Reactive Protosolvated Carboxonium Ion Intermediate?[J]. Journal of the American Chemical Society, 2001, 123 47: 11556-11561. DOI:10.1021/ja011253a.
[8] O. SUGIMOTO. Preparation and reaction of quinolinyl (or pyridinyl)phosphonium salts with base and pivalaldehyde[J]. Heterocycles, 2011, 56 1: 837-847. DOI:10.3987/COM-11-12154.