Isovaleraldehyde

Base Information

• Chemical Name: Isovaleraldehyde
• CAS No.: 590-86-3
• Molecular Formula: C5H10O
• Molecular Weight: 86.1338
• Hs Code.: 29121900
• European Community (EC) Number: 209-691-5
• ICSC Number: 1748
• NSC Number: 404119
• UN Number: 1989,2058,1988
• UNII: 69931RWI96
• DSSTox Substance ID: DTXSID1021619
• Nikkaji Number: J6.754G
• Wikipedia: Isovaleraldehyde
• Wikidata: Q409554
• Metabolomics Workbench ID: 38898
• ChEMBL ID: CHEMBL18360
• Mol file: 590-86-3.mol

Synonyms:Isovaleraldehyde;

Chemical Property of Isovaleraldehyde

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 30 mm Hg ( 20 °C)
• Melting Point: -60 °C
• Refractive Index: n20/D 1.388(lit.)
• Boiling Point: 93.515 °C at 760 mmHg
• Flash Point: -1.667 °C
• PSA: 17.07000
• Density: 0.792 g/cm³
• LogP: 1.23140
• Storage Temp.: Refrigerator (+4°C) + Flammables area
• Solubility.: alcohol: miscible
• Water Solubility.: 15 g/L (20 ºC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 86.073164938
• Heavy Atom Count: 6
• Complexity: 39.2
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

iso-Valeraldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36-36/37/38-43-36/37
• Safety Statements: 7-16-26-36-37/39-37-24-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: CC(C)CC=O
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract. The substance is mildly irritating to the skin. If swallowed the substance may cause vomiting and could result in aspiration pneumonitis.
• Description: May be prepared by oxidation of isoamyl alcohol.
• Uses: Isovaleraldehyde is manufactured by oxidizing isoamyl alcohol with sodium perchromate and sulfuric acid. Isovaleraldehyde is present in essential oils of orange, peppermint, lemon, and other plants and fruits. Its main uses are as an artificial flavor additive and in perfumes. Isovaleraldehyde acts as a reagent in the preparation of active pharmaceutical ingredient (API) products. It serves as an internal standard for the determination of wine aroma carbonyl compounds with 5-8 carbon atoms. Further, it is utilized as a standard to evaluate the quality of olive oils by headspace solid-phase microextraction-gas chromatography using flame ionization detection and multivariate analysis. In addition to this, it is employed to enhance the taste and odor of the food. In artificial flavors and perfumes.

Technology Process of Isovaleraldehyde

There total 296 articles about Isovaleraldehyde 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: 100.0%

3-methyl-2-buten-1-ol (556-82-1) → isovaleraldehyde (590-86-3)

Guidance literature:

With (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen; In tetrahydrofuran; at 23 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2009.04.130

Reference yield: 99.0%

carbon monoxide (201230-82-2) + isobutene (115-11-7,15220-85-6) → isovaleraldehyde (590-86-3)

Guidance literature:

With hydrogen; HSA-Rh(I); In water; pentane; at 60 ℃; for 24h; under 60800 Torr;

DOI:10.1016/S0040-4039(00)00473-1

Reference yield: 98.0%

2-(2-methylpropyl)-1,3-dioxolane (6135-52-0) → isovaleraldehyde (590-86-3)

Guidance literature:

With chloral hydrate; In hexane; at 25 ℃; for 1.5h; Inert atmosphere;

DOI:10.1080/00397911.2013.876652

upstream raw materials:

2,2-dimethyl-oxetane

N-Formylpiperidine

2-methylpropylmagnesium chloride

3-methylbutyric acid

Downstream raw materials:

1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(3-methyl-butane-1,1-diyl)-bis-pyrazol-3-one

ethyl-6-isobutyl-2-methyl-4-oxocyclohex-2-ene-1-carboxylate

cyclohexyl-(3-methyl-butylidene)-amine

isoamyl benzoate

Refernces

Direct catalytic enantioselective α-aminomethylation of aldehydes

10.1002/chem.200600725

The research focuses on the development of a direct catalytic asymmetric a-aminomethylation of aldehydes, a significant advancement in organic chemistry. This reaction provides a pathway to ?-amino aldehydes, which are valuable precursors to ?2-amino acid derivatives and ?-amino alcohols, important in pharmaceuticals. The study explores the use of chiral amine and amino acid catalysts to facilitate the reaction between unmodified aldehydes and a formaldehyde-derived imine precursor. The reactions were conducted under various conditions, with the addition of lithium halide salts found to enhance enantioselectivity. The experiments involved screening different catalysts, such as proline and its derivatives, as well as chiral pyrrolidines, using dibenzylamine-derived aminomethyl ether and isovaleraldehyde as reactants. The enantioselectivity and conversion rates were determined through NMR spectroscopic analyses and chiral-phase HPLC analysis. The results showed that the reactions were fast, highly chemoselective, and yielded the corresponding ?-amino alcohols with high enantiomeric excess (up to 98% ee) after in situ reduction. The research also proposed transition-state models to account for the stereochemical outcomes of the reactions catalyzed by different chiral pyrrolidines and proline derivatives.