Deuterated acetone

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Deuterated acetone
Skeletal formula of deuterated acetone Acetone-d6.png
Skeletal formula of deuterated acetone
Spacefill model of deuterated acetone Acetone-3D-vdW.png
Spacefill model of deuterated acetone
Skeletal formula of deuterated acetone Acetone-3D-balls.png
Skeletal formula of deuterated acetone
Names
Preferred IUPAC name
(1,1,1,3,3,3-2H6)Propan-2-one
Identifiers
3D model (JSmol)
1702935
ChEBI
ChemSpider
ECHA InfoCard 100.010.514 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-563-9
PubChem CID
UNII
UN number 1090
  • InChI=1S/C3H6O/c1-3(2)4/h1-2H3/i1D3,2D3 Yes check.svgY
    Key: CSCPPACGZOOCGX-WFGJKAKNSA-N Yes check.svgY
  • [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H]
Properties
C32H6O or C3D6O
Molar mass 64.1161 g mol−1
Density 0.872 g cm−3
Melting point −94 °C (−137 °F; 179 K)
Boiling point 56 °C (133 °F; 329 K)
Vapor pressure 24.5-25.3 kPa (at 20°C)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H319, H336
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point −19 °C (−2 °F; 254 K)
Related compounds
Related compounds
 Acetone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Deuterated acetone ((CD3)2CO), also known as acetone-d6, is a form (isotopologue) of acetone (CH3)2CO in which the hydrogen atom (H) is replaced with deuterium (heavy hydrogen) isotope (2H or D). Deuterated acetone is a common solvent used in NMR spectroscopy. [1]

Contents

Properties

As with all deuterated compounds, the properties of deuterated acetone are virtually identical to those of regular acetone.

Production

Deuterated acetone is made by the reaction of acetone with heavy water, 2H2O or D2O, in the presence of a base. In this case, the base used is deuterated lithium hydroxide: [1]

Deuteration of acetone.svg

In order to fully deuterate the acetone, the process is repeated several times, distilling off the acetone from the heavy water, and re-running the reaction in a fresh batch of heavy water.

References

  1. 1 2 Paulsen, P. J.; Cooke, W. D. (1963). "Preparation of Deuterated Solvents for Nuclear Magnetic Resonance Spectrometry". Analytical Chemistry. 35 (10): 1560. doi:10.1021/ac60203a072.
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