| Identification | More | [Name]
Trimethylacetaldehyde | [CAS]
630-19-3 | [Synonyms]
2,2-DIMETHYL-1-PROPANAL
2,2-DIMETHYLPROPANAL
2,2-DIMETHYLPROPIONALDEHYDE
PAL
PIVALALDEHYDE
PIVALDEHYDE
TRIMETHYLACETALDEHYDE
2,2-dimethyl-propana
2,2-Dimethylpropionaldehyd
2-Dimethylpropanal
alpha,alpha-Dimethylpropionaldehyde
Neopentaldehyde
Neopentanal
Pivalic aldehyde
Pivalicaldehyde
propanal,2,2-dimethyl-
tert-Butylformaldehyde
tert-C4H9CHO
tert-Pentanal
tert-Valeraldehyde | [EINECS(EC#)]
211-134-6 | [Molecular Formula]
C5H10O | [MDL Number]
MFCD00006962 | [Molecular Weight]
86.13 | [MOL File]
630-19-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless liquid | [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 Gravity]
0.793 | [Water Solubility ]
Negligible | [Sensitive ]
Air Sensitive | [BRN ]
506060 | [Henry's Law Constant]
4.1×10-2 mol/(m3Pa) at 25℃, Wang et al. (2017) | [Dielectric constant]
9.0500000000000007 | [Stability:]
Air Sensitive, Volatile | [InChI]
1S/C5H10O/c1-5(2,3)4-6/h4H,1-3H3 | [InChIKey]
FJJYHTVHBVXEEQ-UHFFFAOYSA-N | [SMILES]
[H]C(=O)C(C)(C)C | [CAS DataBase Reference]
630-19-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Propanal, 2,2-dimethyl-(630-19-3) | [EPA Substance Registry System]
630-19-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS02,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H225-H315-H319-H335 | [Precautionary statements ]
P210-P233-P240-P241-P303+P361+P353-P305+P351+P338 | [Hazard Codes ]
F,Xi,F+ | [Risk Statements ]
R11:Highly Flammable.
R37/38:Irritating to respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S33:Take precautionary measures against static discharges .
S24:Avoid contact with skin . | [RIDADR ]
UN 1989 3/PG 2
| [WGK Germany ]
3
| [F ]
8 | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29121900 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Eye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
3,3-Dimethyl-2-oxobutyric acid-->2-hydroxy-2-methylpropionaldehyde | [Preparation Products]
neopentyl glycol-->Clomazone-->(S)-2-Methylproline-->Methyl isocyanoacetate-->N-(Trimethylsilyl)-2,2-dimethylpropane-1-imine-->2,2-Dimethyl-3-hexanol-->1,9-Bis-Boc-1,5,9-triazanonane-->methyl (2S)-2-amino-3,3-dimethylbutanoate-->2,2-Dimethyl-3-hexanone-->(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone-->Ethyl pivaloylacetate-->2-Amino-5-tert-butyl-1,3,4-thiadiazole-->2R,5S)-5-benzyl-2-tert-butyl-3-MethyliMidazolidin-4-one |
| Questions and Answers (Q&A) | Back Directory | [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. |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless liquid | [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(sp3)–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. | [Synthesis]
Pivaloyl chloride was used as raw material, palladium-carbon poisoned by quinoline-S was used as catalyst, and the reduction reaction was carried out with hydrogen in a solvent to which an acid-binding agent was added, and the reaction solution was sequen | [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.
[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. |
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