Pivaldehyde

Description

Trimethylacetaldehyde (also known as Pivaldehyde) is the trimethyl form of acetaldehyde. It is an aldehyde with a sterically bulky R group, the tertiary-butyl group being attached to the carbonyl, >C=O. It is a useful reagent in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. It is useful in streoselective synthesis application as well as in aldol condensation reactions. As a derivative of acetaldehyde, trimethyl acetaldehyde can be used for the production of acetate. It can also be used as the precursor for manufacturing of pyridine derivatives, pentaerythritol, and crotonaldehyde.

Chemical Properties

Clear colorless liquid

Uses

Trimethylacetaldehyde is used as a stereoselective synthesis application. It is also used as a building block used in aldol condensation reactions. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Uses

Commonly used building block in aldol condensation reactions.

Application

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].

Definition

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.

References

Ho, Tse Lok, et al. Pivaldehyde. Fieser and Fieser's Reagents for Organic Synthesis. John Wiley & Sons, Inc. 2006.
https://en.wikipedia.org/wiki/Acetaldehyde#Uses
https://en.wikipedia.org/wiki/Pivaldehyde
https://www.alfa.com/en/catalog/A15013/

References

[1] A. LAPENA; R. S; J L Mateo. Anionic copolymerization of acrolein with aldehydes. III[J]. Journal of Polymer Science: Polymer Symposia, 1973. 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.