Pinacolone (3,3-dimethyl-2-butanone) is an important

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...

. 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 Triadimefon is a fungicide used in agriculture to control various fungal diseases. As a seed treatment, it is used on barley, corn, cotton, oats, rye, sorghum, and wheat. In fruit it is used on pineapple and banana. Non-food uses include pine ...

and in synthesis of the herbicide metribuzin. The molecule is an unsymmetrical

. The α-methyl group can participate in condensation reactions. The carbonyl group can undergo the usual reactions (hydrogenation, reductive amination, etc.). It is a Schedule 3 compound under the Chemical Weapons Convention 1993, due to being related to

pinacolyl alcohol Pinacolyl alcohol is a common name for 3,3-dimethylbutan-2-ol, also known as pine alcohol. It is one of the isomeric hexanols and a secondary alcohol. Pinacolyl alcohol appears on the List of Schedule 2 substances (CWC) as a precursor for the ne ...

, which is used in the production of

soman Soman (or GD, EA 1210, Zoman, PFMP, A-255, systematic name: ''O''-pinacolyl methylphosphonofluoridate) is an extremely toxic chemical substance. It is a nerve agent, interfering with normal functioning of the mammalian nervous system by inhibiti ...

. It is also a controlled export in

Australia Group The Australia Group is a multilateral export control regime (MECR) and an informal group of countries (now joined by the European Commission) established in 1985 (after the use of chemical weapons by Iraq in 1984) to help member countries to i ...

member states.

Preparation

Most famously, at least in the classroom, pinacolone arises by the

pinacol rearrangement The pinacol–pinacolone rearrangement is a method for converting a 1,2-diol to a carbonyl compound in organic chemistry. The 1,2-rearrangement takes place under acidic conditions. The name of the rearrangement reaction comes from the rearrangemen ...

, which occurs by protonation of

pinacol Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms. Preparation It may be produced by the pinacol coupling reaction from acetone: Reactions As a vicinal-diol, it can rearrange t ...

(2,3-dimethylbutane-2,3-diol). : 800px-Pinacol rearragement

Industrially pinacolone is made by the hydrolysis of 4,4,5-trimethyl-1,3-

dioxane 1,4-Dioxane () is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers ( 1,2- ...

, which is the product of isoprene and formaldehyde via the

Prins reaction The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H+ ion. The outcome of the reaction depends on reaction c ...

. It also is generated by

ketonization In organic chemistry, ketonic decarboxylation (also known as decarboxylative ketonization) 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 w ...

pivalic acid Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (''t''-BuC(O)) is Piv and for pivalic acid ...

and acetic acid or acetone over metal oxide catalysts. 3-Methylbutanal is a starting material for 2,3-dimethyl-2-butene, which in turn is converted to pinacolone. Pinacolone can also be produced from 2-methy-2-butanol when reacted with C5 alcohols.

Drug Uses

Pinacolone is produced in large amounts for use in fungicides, herbicides, and pesticides. #

retrosynthetic analysis Retrosynthetic analysis is a technique for solving problems in the planning of organic syntheses. This is achieved by transforming a target molecule into simpler precursor structures regardless of any potential reactivity/interaction with reagents. ...

of vibunazole showed that it was derived from pinacolone. #It is also used to prepare

pinacidil Pinacidil is a cyanoguanidine drug that opens ATP-sensitive potassium channels producing peripheral vasodilatation of arterioles. It reduces blood pressure Blood pressure (BP) is the pressure of circulating blood against the walls of blood ...

, as well as naminidil. #

Stiripentol Stiripentol, sold under the brand name Diacomit, is an anticonvulsant medication used for the treatment of Dravet syndrome - a serious genetic brain disorder. The most common side effects include loss of appetite, weight loss, insomnia (difficu ...

# Tribuzone # Pivaloylacetonitrile is used in the synthesis of Doramapimod. #

Triadimefon Triadimefon is a fungicide used in agriculture to control various fungal diseases. As a seed treatment, it is used on barley, corn, cotton, oats, rye, sorghum, and wheat. In fruit it is used on pineapple and banana. Non-food uses include pine ...

# Diclobutrazole #

Paclobutrazol Paclobutrazol (PBZ) is the ISO common name for an organic compound that is used as a plant growth retardant and triazole fungicide. It is a known antagonist of the plant hormone gibberellin, acting by inhibiting gibberellin biosynthesis, reduc ...

# Valconazole #

Diethylstilbestrol Diethylstilbestrol (DES), also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for those with a ...

pinacolone 8922-13-9 #Some kind of

Bisphenol A Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial s ...

derivative also # Thiofanox

References

{{Chemical agents Hexanones Tert-butyl compounds Nerve agent precursors

Preparation

Drug Uses

See also

References