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Pinacolone information


Pinacolone
Skeletal formula of pinacolone
Skeletal formula of 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 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1209331
ChEBI
  • CHEBI:197349
ChemSpider
  • 6176 checkY
ECHA InfoCard 100.000.838 Edit this at Wikidata
EC Number
  • 200-920-4
MeSH Pinacolone
PubChem CID
  • 6416
RTECS number
  • EL7700000
UNII
  • 3U1AAG3528 checkY
UN number 1224
CompTox Dashboard (EPA)
  • DTXSID5021752 Edit this at Wikidata
InChI
  • InChI=1S/C6H12O/c1-5(7)6(2,3)4/h1-4H3 checkY
    Key: PJGSXYOJTGTZAV-UHFFFAOYSA-N checkY
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)
-69.86·10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS07: Exclamation mark
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
checkY verify (what is checkY☒N ?)
Infobox references

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.[2] It is also a controlled export in Australia Group member states.[3]

  1. ^ "Pinacolone | C6H12O | ChemSpider".
  2. ^ Handbook of chemical and biological warfare agents (2nd ed.). CRC Press. 24 August 2007. ISBN 9780849314346.
  3. ^ "Export Control List: Chemical Weapons Precursors". Australia Group. australiagroup.net. Retrieved 7 April 2017.

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Pinacolone

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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...

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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...

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Pinacol

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coupling reaction from acetone: As a vicinal-diol, it can rearrange to pinacolone by the pinacol rearrangement, e.g. by heating with sulfuric acid: Pinacol...

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Pivalic acid

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ampicillin and amoxycillin. It was originally prepared by the oxidation of pinacolone with chromic acid and by the hydrolysis of tert-butyl cyanide. Convenient...

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C6H12O

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cis-3-Hexen-1-ol Methyl isobutyl ketone 3-Methyl-2-pentanone Oxepane Pinacolone This set index page lists chemical structure articles associated with...

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Isovaleraldehyde

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3-dimethylbutane-2,3-diol and methyl tert-butyl ketone, better known as pinacolone. Pinacolone itself is then used in synthesis for number of pesticides. Additionally...

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Pivaldehyde

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acid - corresponding carboxylic acid Pivalamide - corresponding amide Pinacolone - corresponding methyl ketone Conant, J. B.; Webb, C. N.; Mendum, W. C...

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Enolate

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Seebach, Dieter (1988). "Structure and Reactivity of Lithium Enolates. From Pinacolone to SelectiveC-Alkylations of Peptides. Difficulties and Opportunities...

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Organolithium reagent

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Seebach, D (1988). "Structure and Reactivity of Lithium Enolates. From Pinacolone to Selective C-Alkylations of Peptides. Difficulties and Opportunities...

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Paclobutrazol

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filed by an ICI group working at Jealott's Hill. 4-Chlorobenzaldehyde and pinacolone are combined in an aldol condensation to form a chalcone which is hydrogenated...

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Hexanone

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sec-butyl ketone) 3,3-Dimethyl-2-butanone (Methyl tert-butyl ketone, Pinacolone) 3-Hexanone (Ethyl propyl ketone) 2-Methyl-3-pentanone (Ethyl isopropyl...

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Wilhelm Rudolph Fittig

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from acetone, followed by the rearrangement to 3,3-dimethylbutanone (pinacolone), which was then oxidised with dichromate to trimethylacetic acid. Fittig's...

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Spiro compound

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[verification needed] Some spiro compounds can be synthesized using the Pinacol-pinacolone rearrangement;: 985  for example, spiro[4.5]decane (final compound in...

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Dimethylmagnesium

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with Benzophenone and of Methylmagnesium Bromide-Magnesium Bromide with Pinacolone". J. Org. Chem. 27 (2): 596–598. doi:10.1021/jo01049a060. Richard A. Andersen...

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Bjerrum defect

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guest molecules in clathrates of many larger organic molecules, such as pinacolone and tetrahydrofuran. In such cases the guest-host hydrogen bonds result...

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Perfluorobutanesulfonyl fluoride

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enolate. This effect is particularly evident with the lithium enolate of pinacolone, which gives a 2:1 mixture favoring C-attack. More substituted lithium...

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