Pivaldehyde

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Cat Number

CHE630193

CAS Number

630-19-3

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Product Detail Description Scientific Support Customer Q&A

CAS Number

630-19-3

EINECS

211-134-6

Storage

2-8℃

Synonyms

2,2-dimethyl-propana; 2,2-Dimethylpropionaldehyd; trimethylacetaldehyde

Molecular Formula

C5H10O

Molecular Weight

86.13

Smiles

[H]C(=O)C(C)(C)C

Appearance

Clear colorless liquid

Melting Point

6 ℃

Boiling Point

75 ℃

Relative Density

0.79

General Description

Pivaldehyde features a sterically-demanding tertiary-butyl group connected to a formyl group. It is a colorless/light yellow liquid that is reactive but also selective. Pivaldehyde is known for its utility in organic synthesis, especially in applications involving uncommon chemistry or pharmaceutical intermediates.

Mechanism of Action

Pivaldehyde reacts much differently from typical linear aldehydes due to its branching. The tert-butyl substituent allows for more controlled reactions when producing stereoselective products, making it useful for aldol reactions and enantiomerically pure ligands.

Application

Medicinal applications of Pivaldehyde include its role as an intermediate in the synthesis of some pharmaceuticals such as anti-hypertensive drugs and antivirals. Pivaldehyde can also be used to produce pesticides and herbicides in agrochemical applications. Due to the numerous derivatives of pivaldehyde that can be synthesized, it also sees use in some specialty fragrance and flavor chemicals as well as advanced polymer production.

Traditional aldehyde decarbonylation mainly produces C-H bonds, but recent advances enable C-C bond formation. Quinoline-2,4-diones are important N-heterocycles found in pharmaceuticals and natural products with diverse biological activities. Existing synthetic methods often require multiple steps or complex substrates, while radical cascade cyclizations offer improved atom and step economy.
Building on previous work using dicumyl peroxide for the methylation and carbonylation/cyclization of aldehydes, Zhang C et al. employed Pivaldehyde as a tert-butyl radical source. Optimization with o-cyanoarylacrylamide 1a and pivaldehyde using 3.0 equiv TBPB in CH₃CN at 100℃ gave a 17% initial yield. Solvent screening (THF, DMSO, toluene, PhCl, 1,4-dioxane) demonstrated significant solvent effects on cyclization efficiency. This transformation provides facile access to valuable tert-butyl substituted quinolone-2,4-diones through a straightforward radical cascade process.

Fig. 1 Decarbonylative cascade cyclization with Pivaldehyde. (Zhang C.; et al. 2022)

References

Zhang C.; et al. Decarbonylative cascade cyclization of ortho-cyanoarylacrylamides with pivaldehyde: Access to tert-butyl containing quinolone-2, 4 (1H, 3H)-diones. Tetrahedron, 2022, 103: 132547.

What is Pivaldehyde's defining structural characteristic?

Sterically-hindered tertiary-butyl group attached to aldehyde.

Can Pivaldehyde dissolve in water?

Insoluble in water. However, freely soluble in most organic solvents such as ethanol, ether, and chloroform.

Is Pivaldehyde pharmaceutical grade?

We provide our customers with quality research & industrial grade products that conform to company & global chemical specifications.

Is Pivaldehyde sensitive to air and light?

Yes, it is both air and light-sensitive.