Pivaldehyde Chemical Properties

Melting point:

6 °C(lit.)

Boiling point:

74 °C730 mm Hg(lit.)

Density 

0.793 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.378(lit.)

Flash point:

4 °F

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless

Specific Gravity

0.793

Water Solubility 

Negligible

Sensitive 

Air Sensitive

BRN 

506060

Dielectric constant

9.0500000000000007

Stability:

Air Sensitive, Volatile

InChIKey

FJJYHTVHBVXEEQ-UHFFFAOYSA-N

CAS DataBase Reference

630-19-3(CAS DataBase Reference)

NIST Chemistry Reference

Propanal, 2,2-dimethyl-(630-19-3)

EPA Substance Registry System

Propanal, 2,2-dimethyl- (630-19-3)

Safety Information

Hazard Codes 

F,Xi,F+

Risk Statements 

11-37/38-43

Safety Statements 

16-23-33-24

RIDADR 

UN 1989 3/PG 2

WGK Germany 

3

F 

8

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29121900

MSDS

• Language:English Provider:Trimethylacetaldehyde
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Pivaldehyde Usage And Synthesis

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

Commonly used building block in aldol condensation reactions.

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.

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.

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].

References

[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.
[9] 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.
[10] SUNG MAN PARK Chan H K Yu Ran Lee. Conformational Structures of Neutral and Cationic Pivaldehyde Revealed by IR-Resonant VUV-MATI Mass Spectroscopy.[J]. International Journal of Molecular Sciences, 2022, 23 23. DOI:10.3390/ijms232314777.

Pivaldehyde(630-19-3)Related Product Information

• Pivaloyl chloride
• Neopentylamine
• Pivalic acid
• Trimethylacetonitrile
• Iodomethyl pivalate
• PotassiuM triMethylacetate, 95%
• TRIMETHYLACETIC ANHYDRIDE
• 2,2-DIMETHYL-6,6,7,7,8,8,8-HEPTAFLUORO-3,5-OCTANEDIONE
• TETRAMETHYL-1,3-CYCLOBUTANEDIONE
• CHLOROMETHYL PIVALATE
• Diethyl 1,1-cyclopropanedicarboxylate
• 1-Phenyl-1-cyclopropanecarboxylic acid
• PR(TMHD)3
• 1-Bromopinacolone
• TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)DYSPROSIUM(III)
• Trimethylacetaldehyde oxime
• Propionaldehyde
• tert-Butanol
• Trimethylacetaldehyde