Pinacolone

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 (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. It is also a controlled export in Australia Group member states.

Pinacolone
Names
Preferred IUPAC name
3,3-Dimethylbutan-2-one
Other names
t-Butyl methyl ketone
1,1,1-Trimethylacetone
Identifiers
3D model (JSmol)
1209331
ChEBI
ChemSpider
ECHA InfoCard 100.000.838
EC Number
  • 200-920-4
MeSH Pinacolone
RTECS number
  • EL7700000
UNII
UN number 1224
  • InChI=1S/C6H12O/c1-5(7)6(2,3)4/h1-4H3 Y
    Key: PJGSXYOJTGTZAV-UHFFFAOYSA-N Y
  • CC(=O)C(C)(C)C
Properties
C6H12O
Molar mass 100.161 g·mol−1
Appearance Colorless liquid
Density 0.801 g cm−3
Melting point −52 °C (−62 °F; 221 K)
Boiling point 103 to 106 °C (217 to 223 °F; 376 to 379 K)
-69.86·10−6 cm3/mol
Hazards
GHS labelling:
Danger
H225, H302, H315, H319, H332, H335, H412
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
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