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Pivaldehyde

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Pivaldehyde Basic information
Product Name:Pivaldehyde
Synonyms:PIVALDEHYDE;2,2-dimethyl-propana;2,2-Dimethylpropionaldehyd;2-Dimethylpropanal;alpha,alpha-Dimethylpropionaldehyde;Neopentaldehyde;Neopentanal;Pivalicaldehyde
CAS:630-19-3
MF:C5H10O
MW:86.13
EINECS:211-134-6
Product Categories:Aldehydes;Building Blocks;C1 to C6;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Aliphatics;Miscellaneous Reagents;API intermediates;bc0001
Mol File:630-19-3.mol
Pivaldehyde Structure
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.)
Fp 4 °F
storage temp. 2-8°C
solubility Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
form Liquid
color Clear colorless
Specific Gravity0.793
Water Solubility Negligible
Sensitive Air Sensitive
BRN 506060
Dielectric constant9.0500000000000007
Stability:Air Sensitive, Volatile
InChIKeyFJJYHTVHBVXEEQ-UHFFFAOYSA-N
CAS DataBase Reference630-19-3(CAS DataBase Reference)
NIST Chemistry ReferencePropanal, 2,2-dimethyl-(630-19-3)
EPA Substance Registry SystemPropanal, 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
8
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29121900
MSDS Information
ProviderLanguage
Trimethylacetaldehyde English
SigmaAldrich English
ACROS English
ALFA English
Pivaldehyde Usage And Synthesis
DescriptionTrimethylacetaldehyde (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 PropertiesClear colorless liquid
UsesTrimethylacetaldehyde 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.
UsesCommonly used building block in aldol condensation reactions.
DefinitionChEBI: 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.
ApplicationPivaldehyde 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(sp3)–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.
Tag: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