2-Methylpropanal

Base Information

• Chemical Name: 2-Methylpropanal
• CAS No.: 78-84-2
• Deprecated CAS: 26140-46-5
• Molecular Formula: C4H8O
• Molecular Weight: 72.1069
• Hs Code.: 2912.13 Oral rat LD50: 960 mg/kg
• European Community (EC) Number: 201-149-6
• ICSC Number: 0902
• NSC Number: 6739
• UN Number: 2045
• UNII: C42E28168L
• DSSTox Substance ID: DTXSID9021635
• Nikkaji Number: J1.483D
• Wikipedia: Isobutyraldehyde
• Wikidata: Q418164
• Metabolomics Workbench ID: 44776
• ChEMBL ID: CHEMBL1404017
• Mol file: 78-84-2.mol

Synonyms:Isobutyraldehyde(8CI);2-Formylpropane;2-Methyl-1-propanal;2-Methylpropanal;2-Methylpropionaldehyde;2-Propanecarboxaldehyde;Dimethylacetaldehyde;Isobutanal;Isobutyral;Isobutyric aldehyde;Isobutyryl aldehyde;Isopropylcarboxaldehyde;Isopropylformaldehyde;NSC 6739;iso-Butyraldehyde;a-Methylpropionaldehyde;

Chemical Property of 2-Methylpropanal

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 147mmHg at 25°C
• Melting Point: -65 °C(lit.)
• Refractive Index: 1.3790
• Boiling Point: 67.131 °C at 760 mmHg
• Flash Point: -24 °C
• PSA: 17.07000
• Density: 0.782 g/cm³
• LogP: 0.84130
• Water Solubility.: 75 g/L (20℃)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 72.057514874
• Heavy Atom Count: 5
• Complexity: 30.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F:Flammable;;
• Statements: R11:; R22:
• Safety Statements: S16:; S29:; S33:; S9:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: CC(C)C=O
• Inhalation Risk: No indication can be given whether a harmful concentration in the air will be reached.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance at very high concentrations is irritating to the upper respiratory tract. If swallowed the substance may cause vomiting and could result in aspiration pneumonitis. Medical observation is indicated. The substance may cause effects on nervous system. Exposure could cause lowering of consciousness.
• Effects of Long Term Exposure: Repeated or chronic inhalation of the vapour may cause chronic inflammation of the upper respiratory tract.
• General Description: 2-Methylpropanal (isobutyraldehyde) serves as a co-reductant in the aerobic epoxidation of olefins catalyzed by μ-oxo-bisiron(III) porphyrins, significantly enhancing reactivity under ambient conditions. This catalytic system achieves high turnover numbers and selectivity, demonstrating its utility in efficient and environmentally friendly epoxide production. (Note: The first abstract did not contain relevant conclusions about 2-methylpropanal, so the response is based on the second abstract.)

Technology Process of 2-Methylpropanal

There total 633 articles about 2-Methylpropanal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

N-(Benzylidene)-2-methyl-1-propenylamine (68003-61-2) → benzaldehyde (100-52-7) + isobutyraldehyde (78-84-2)

Guidance literature:

With hydrogenchloride; In dichloromethane; for 1h; Heating;

DOI:10.1021/jo00047a034

Reference yield:

N-(p-nitrophenyl)-2-methylprop-1-enamine (125519-77-9) → 4-nitro-aniline (100-01-6,104810-17-5) + isobutyraldehyde (78-84-2)

Guidance literature:

With hydrogenchloride; water; In dimethylsulfoxide-d6; at 25 ℃; Rate constant; Mechanism; I = 1.00 M KCl;

DOI:10.1021/jo00295a017

Reference yield:

N-methyl-N-(p-nitrophenyl)-2-methylprop-1-enamine (125519-96-2) → isobutyraldehyde (78-84-2) + N-methyl(p-nitroaniline) (100-15-2)

Guidance literature:

With hydrogenchloride; water; at 25 ℃; Rate constant; Mechanism; I = 1.00 M KCl;

DOI:10.1021/jo00295a017

upstream raw materials:

2-methyl-1,2-epoxypropane

1,4-dioxane

N,N-dimethylisobutylamine

chloranil

Downstream raw materials:

1-(2-methylprop-1-en-1-yl)pyrrolidine

4-methyl-pent-2-enoic acid amide

2,2-dimethyl-3-piperidin-1-yl-propionaldehyde

2,2-dimethyl-3-(N-morpholino)propanal

Refernces

Unexpected Direct Synthesis of N-Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition

10.1002/anie.201702727

The research presents an unexpected direct method for synthesizing industrially significant N-vinyl amides from aldehydes and esters using vinyl azide–enolate [3+2] cycloaddition. The study initially explored alkylation reactions of an ester with alkyl iodides to access quaternary esters but fortuitously discovered the formation of N-vinyl amides when using a two-carbon-atom iodo azide. This led to a comprehensive investigation of the reactivity of various esters and aldehydes with iodo azide 14. The reaction likely proceeds through an initial [3+2] cycloaddition involving a vinyl azide generated in situ, followed by rearrangement and nitrogen extrusion. Aldehydes such as aldehyde 27, isobutyraldehyde 29, aldehydes 30 and 32. The research employed quantum computational analysis to support the proposed mechanism and to estimate the activation energies for the cycloaddition with different azides. The study provides new insights into atom-efficient amide synthesis and suggests a potential reevaluation of azidoethene as a synthetic reagent, with implications for drug formulation, tissue engineering, and the development of poly(vinyl amide) polymers.

Remarkable enhancement of aerobic epoxidation reactivity for olefins catalyzed by μ-oxo-bisiron(III) porphyrins under ambient conditions

10.1016/j.tetlet.2009.09.061

This research aimed to develop an efficient catalytic system for the aerobic epoxidation of olefins using l-oxo-bisiron(III) porphyrins [(FeIIITPP)2O] as catalysts, isobutylaldehyde as co-reductants, and dioxygen as the oxidant. The study demonstrated a significant enhancement in reactivity compared to mono-metalloporphyrin catalysts, achieving a turnover number (TON) of up to 1400 million for the catalyst. The researchers proposed a plausible mechanism involving both binuclear and mononuclear intermediates and confirmed the formation of high-valent iron intermediates through in situ UV–vis spectroscopy. The results showed that the catalytic system was highly active and selective under ambient conditions, with excellent performance across various substrates, making it a promising approach for the production of epoxides in an economical and environmentally friendly manner.