3-Methyl-3-penten-2-one

Last updated
3-Methyl-3-penten-2-one
3-Methyl-3-penten-2-one.svg
Names
Preferred IUPAC name
3-Methylpent-3-en-2-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.008.440 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-283-7
PubChem CID
UNII
  • InChI=1S/C6H10O/c1-4-5(2)6(3)7/h4H,1-3H3/b5-4+
    Key: ZAMCMCQRTZKGDX-SNAWJCMRSA-N
  • C/C=C(\C)/C(=O)C
Properties
C6H10O
Molar mass 98.145 g·mol−1
AppearanceClear liquid
Density 0.875 g/cm3 (at 20 °C)
Hazards
GHS pictograms GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
GHS Signal word Danger
H226, H302, H312, H315, H319, H331, H332, H335
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+312, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P311, P312, P321, P322, P330, P332+313, P337+313, P362
Flash point 34 °C (93 °F) (closed cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 (methyl sec-butyl ketone) and is obtained by acid-catalyzed dehydration of 4-hydroxy-3-methyl-2-pentanone. It is used as an intermediate in organic chemistry syntheses. [1]

3-Methyl-2-pentanone synthesis.svg

Related Research Articles

Ketone Class of organic compounds having structure RCOR´

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 Chemical compound

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.

Iodoform Chemical compound

Iodoform (also known as triiodomethane and, inaccurately, as carbon triiodide) is the organoiodine compound with the formula CHI3. A pale yellow, crystalline, volatile substance, it has a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

2-Pentanone Chemical compound

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 Chemical compound

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:

Ozonolysis is an organic reaction where the unsaturated bonds of alkenes, alkynes, or azo compounds are cleaved with ozone. Alkenes and alkynes form organic compounds in which the multiple carbon–carbon bond has been replaced by a carbonyl group while azo compounds form nitrosamines. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.

Methyl isobutyl ketone Chemical compound

Methyl isobutyl ketone (MIBK) is the organic compound with the formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

Mesityl oxide Chemical compound

Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.

Danishefsky Taxol total synthesis

The Danishefsky Taxol total synthesis in organic chemistry is an important third Taxol synthesis published by the group of Samuel Danishefsky in 1996 two years after the first two efforts described in the Holton Taxol total synthesis and the Nicolaou Taxol total synthesis. Combined they provide a good insight in the application of organic chemistry in total synthesis.

Ethyl isopropyl ketone Chemical compound

Ethyl isopropyl ketone (2-methyl-3-pentanone) is an aliphatic ketone with used as a reagent in organic chemistry and as a solvent.

The Corey–Kim oxidation is an oxidation reaction used to synthesise aldehydes and ketones from primary and secondary alcohols. It is named for American chemist and Nobel Laureate Elias James Corey and Korean-American chemist Choung Un Kim.

The molecular formula C5H10O may refer to:

The molecular formula C6H12O may refer to:

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:

<i>N</i>-<i>tert</i>-Butylbenzenesulfinimidoyl chloride Chemical compound

N-tert-Butylbenzenesulfinimidoyl chloride is a useful oxidant for organic synthesis reactions. It is a good electrophile, and the sulfimide S=N bond can be attacked by nucleophiles, such as alkoxides, enolates, and amide ions. The nitrogen atom in the resulting intermediate is basic, and can abstract an α-hydrogen to create a new double bond.

3-Hexanone Chemical compound

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-2-pentanone Chemical compound

3-Methyl-2-pentanone 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.

Alpha-beta Unsaturated carbonyl compounds

α,β-Unsaturated carbonyl compounds refers to organic compounds with the general structure (O=CR)−Cα=Cβ-R. Examples would be enones and enals. In these compounds the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.

References

  1. Hardo Siegel, Manfred Eggersdorfer (2007), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5