Deuterated acetone

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

Deuterated acetone
Skeletal formula of deuterated acetone
Skeletal formula of deuterated acetone
Spacefill model of deuterated acetone
Spacefill model of deuterated acetone
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
EC Number
  • 211-563-9
UNII
UN number 1090
  • InChI=1S/C3H6O/c1-3(2)4/h1-2H3/i1D3,2D3 checkY
    Key: CSCPPACGZOOCGX-WFGJKAKNSA-N checkY
  • [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H]
Properties
C32H6O
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:
GHS02: FlammableGHS07: Exclamation mark
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 four-colored diamond
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).
Infobox references

Properties

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

Manufacture

Deuterated acetone is prepared from heavy water, D2O, by what amounts to an aldol reaction. In this case, the base used is a deuterated version of lithium hydroxide:[1]

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. P. J. Paulsen, W. D. Cooke. . Anal. Chem., 1963, 35 (10), pp 1560–1560. DOI: 10.1021/ac60203a072


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