Deuterated acetone

Deuterated acetone
Skeletal formula of deuterated acetone	Spacefill model of deuterated acetone
Names
	Preferred IUPAC name (1,1,1,3,3,3-2H6)Propan-2-one
Identifiers
CAS Number	666-52-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1702935
ChEBI	CHEBI:78217 ;
ChemSpider	455535 ;
ECHA InfoCard	100.010.514
EC Number	211-563-9;
PubChem CID	522220;
UNII	B0N19B53H8 ;
UN number	1090
CompTox Dashboard (EPA)	DTXSID20216767 ;
	InChI InChI=1S/C3H6O/c1-3(2)4/h1-2H3/i1D3,2D3 Key: CSCPPACGZOOCGX-WFGJKAKNSA-N ;
	SMILES [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H];
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H225, H319, H336
Precautionary statements	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)	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

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]

Properties

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

Manufacture

Deuterated acetone is prepared 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]

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

^ ^a ^b 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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[Paulsen-1] 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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