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Names | |
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Preferred IUPAC name 3-Methylpentan-2-one | |
Other names Methyl sec-Butyl ketone | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.008.439 ![]() |
EC Number |
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PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H12O | |
Molar mass | 100.161 g·mol−1 |
Appearance | Colorless liquid |
Odor | Peppermint-like |
Density | 0.8130 g/mL (20 °C) |
Melting point | −83 °C (−117 °F; 190 K) |
Boiling point | 116 °C (241 °F; 389 K) |
2.26 wt % (20 °C) | |
Refractive index (nD) | 1.4012 (20 °C) |
Hazards | |
GHS labelling: [1] | |
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Danger | |
H225 | |
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |
Flash point | 12 °C (54 °F; 285 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
3-Methyl-2-pentanone (methyl sec-butyl ketone) is an aliphatic ketone and isomer of 2-hexanone. It is used as a solvent and as an intermediate for syntheses. Its industrial importance is low. It is produced by base-catalyzed aldol condensation of 2-butanone with acetaldehyde, forming 4-hydroxy-3-methyl-2-pentanone, which is dehydrated to 3-methyl-3-penten-2-one over an acid catalyst, followed by hydrogenation over a palladium catalyst. [2]
In chemistry, a ketone is a functional group with the structure R2C=O, where R can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond). The simplest ketone is acetone (R = R' = methyl), with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.
Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.
Methyl ethyl ketone peroxide (MEKP) is an organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless oily liquid. It is widely used in vulcanization (crosslinking) of polymers.
2-Pentanone or methyl propyl ketone (MPK) is a ketone and solvent of minor importance. It is comparable to methyl ethyl ketone, but has a lower solvency and is more expensive. It occurs naturally in Nicotiana tabacum (Tobacco) and blue cheese as a metabolic product of Penicillium mold growth.
3-Pentanone is a simple, symmetrical dialkyl ketone. It is a colorless liquid ketone with an odor like that of acetone. It is soluble in about 25 parts water, but miscible with organic solvents.
Pentanone may refer to the following ketones containing five carbon atoms:
The Mannich reaction is an organic reaction which consists of an amino alkylation of an acidic proton placed next to a carbonyl functional group by formaldehyde and a primary or secondary amine or ammonia. The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after chemist Carl Mannich.
Methyl isobutyl ketone (MIBK) is the common name for the organic compound 4-methylpentan-2-one, condensed chemical formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.
The Wieland–Miescher ketone is a racemic bicyclic diketone (enedione) and is a versatile synthon which has so far been employed in the total synthesis of more than 50 natural products, predominantly sesquiterpenoids, diterpenes and steroids possessing possible biological properties including anticancer, antimicrobial, antiviral, antineurodegenerative and immunomodulatory activities. The reagent is named after two chemists from Ciba Geigy, Karl Miescher and Peter Wieland. Examples of syntheses performed using the optically active enantiomer of this diketone as a starting material are that of ancistrofuran and the Danishefsky total synthesis of Taxol.
Ethyl isopropyl ketone (2-methyl-3-pentanone) is an aliphatic ketone with used as a reagent in organic chemistry and as a solvent.
Oppenauer oxidation, named after Rupert Viktor Oppenauer, is a gentle method for selectively oxidizing secondary alcohols to ketones.
In chemistry, the Noyori asymmetric hydrogenation refers to methodology for enantioselective reduction of ketones and related functional groups. This methodology was introduced by Ryoji Noyori, who shared the Nobel Prize in Chemistry in 2001 for contributions to asymmetric hydrogenation. These hydrogenations are used in the production of several drugs, such as the antibacterial levofloxin, the antibiotic carbapenem, and the antipsychotic agent BMS181100.
The molecular formula C5H10O may refer to:
The molecular formula C6H12O may refer to:
Pinacolone (3,3-dimethyl-2-butanone) is an important ketone in organic chemistry. It is a colorless liquid and has a slight peppermint- or camphor- odor. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. The molecule is an unsymmetrical ketone. The α-methyl group can participate in condensation reactions. The carbonyl group can undergo the usual reactions. It is a Schedule 3 compound under the Chemical Weapons Convention 1993, due to being related to pinacolyl alcohol, which is used in the production of soman. It is also a controlled export in Australia Group member states.
Heptanone may refer to the following ketones with seven carbon atoms the formula C7H14O:
Hexanone may refer to the following ketones containing six carbon atoms:
Ketonic decarboxylation is a type of organic reaction and a decarboxylation converting two equivalents of a carboxylic acid to a symmetric ketone by the application of heat with expulsion of one equivalent of water and one equivalent of carbon dioxide. Bases promote this reaction. The reaction mechanism likely involves nucleophilic attack of the alpha-carbon of one acid group on the other acid group's carbonyl, possibly as a concerted reaction with the decarboxylation. The initial formation of an intermediate carbanion with decarboxylation from one acid group prior to the nucleophilic attack has been proposed, but is unlikely since the byproduct resulting from the carbanion's protonation by the acid has never been reported. This reaction is different from oxidative decarboxylation, which proceeds through a radical mechanism and is characterised by a different product distribution in isotopic labeling experiments with two different carboxylic acids. With two different carboxylic acids, the reaction behaves poorly because of poor selectivity except when one of the acids is used in large excess.
3-Hexanone (ethyl propyl ketone) is an organic compound with the formula C6H12O. It is a ketone used as a solvent and as a chemical intermediate.
3-Methyl-3-penten-2-one is an unsaturated aliphatic ketone. It is an isomer of mesityl oxide and isomesityl oxide. It is a precursor of 3-methyl-2-pentanone and is obtained by acid-catalyzed dehydration of 4-hydroxy-3-methyl-2-pentanone. It is used as an intermediate in organic chemistry syntheses.