Contents

Pinacolone

Pinacolone

Skeletal formula Ball-and-stick model
Names
Preferred IUPAC name 3,3-Dimethylbutan-2-one
Other names t-Butyl methyl ketone 1,1,1-Trimethylacetone
Identifiers
CAS Number	75-97-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1209331
ChEBI	CHEBI:197349
ChemSpider	6176 Y
ECHA InfoCard	100.000.838
EC Number	200-920-4
MeSH	Pinacolone
PubChem CID	6416
RTECS number	EL7700000
UNII	3U1AAG3528 Y
UN number	1224
CompTox Dashboard (EPA)	DTXSID5021752
InChI InChI=1S/C6H12O/c1-5(7)6(2,3)4/h1-4H3 Y Key: PJGSXYOJTGTZAV-UHFFFAOYSA-N Y
SMILES CC(=O)C(C)(C)C
Properties
Chemical formula	C6H12O
Molar mass	100.161 g·mol−1
Appearance	Colorless liquid
Density	0.801 g cm−3
Melting point	−52[1] °C (−62 °F; 221 K)
Boiling point	103 to 106 °C (217 to 223 °F; 376 to 379 K)
Magnetic susceptibility (χ)	-69.86·10−6cm3/mol
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H315, H319, H332, H335, H412
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	1 4 0
Flash point	5 °C (41 °F; 278 K)
Safety data sheet (SDS)	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Chemical compound

Pinacolone (3,3-dimethyl-2-butanone) is an important ketoneinorganic 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 (hydrogenation, reductive amination, etc.). 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.^[2] It is also a controlled export in Australia Group member states.^[3]

Preparation[edit]

Most famously, at least in the classroom, pinacolone arises by the pinacol rearrangement, which occurs by protonation of pinacol (2,3-dimethylbutane-2,3-diol).^[4]

Industrially pinacolone is made by the hydrolysis of 4,4,5-trimethyl-1,3-dioxane, which is the product of isoprene and formaldehyde via the Prins reaction. It also is generated by ketonizationofpivalic 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.^[5]

Drug Uses[edit]

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

1. retrosynthetic analysisofvibunazole showed that it was derived from pinacolone.
2. It is also used to prepare pinacidil, as well as naminidil.
3. Stiripentol
4. Tribuzone
5. Pivaloylacetonitrile is used in the synthesis of Doramapimod.
6. Triadimefon
7. Diclobutrazole
8. Paclobutrazol
9. Valconazole
10. Diethylstilbestrol pinacolone [18922-13-9].^[6]
11. Some kind of Bisphenol A derivative also U.S. patent 4,599,463
12. Thiofanox

See also[edit]

• Pinacol
• Pinacolyl alcohol
• Soman

References[edit]