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
Acetone-3D-balls.png
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 (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. [1]

Contents

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, D2O, in the presence of a base. In this case, the base used is a deuterated version of 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.

Related Research Articles

<span class="mw-page-title-main">Deuterium</span> Isotope of hydrogen with one neutron

Deuterium (or hydrogen-2, symbol 2
H
or D, also known as heavy hydrogen) is one of two stable isotopes of hydrogen (the other being protium, or hydrogen-1). The nucleus of a deuterium atom, called a deuteron, contains one proton and one neutron, whereas the far more common protium has no neutrons in the nucleus. Deuterium has a natural abundance in Earth's oceans of about one atom of deuterium among every 6,420 atoms of hydrogen (see heavy water). Thus deuterium accounts for approximately 0.0156% by number (0.0312% by mass) of all the naturally occurring hydrogen in the oceans (i.e., 4.85×1013 tonnes of deuterium – mainly in form of HOD and only rarely in form of D2O – in 1.4×1018 tonnes of water), while protium accounts for 99.98%. The abundance of deuterium changes slightly from one kind of natural water to another (see Vienna Standard Mean Ocean Water)

<span class="mw-page-title-main">Heavy water</span> Form of water

Heavy water is a form of water whose hydrogen atoms are all deuterium rather than the common hydrogen-1 isotope that makes up most of the hydrogen in normal water. The presence of the heavier hydrogen isotope gives the water different nuclear properties, and the increase in mass gives it slightly different physical and chemical properties when compared to normal water.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

Chloroform, or trichloromethane, is an organic compound with the formula CHCl3 and a common solvent. It is a very volatile, colorless, strong-smelling, dense liquid produced on a large scale as a precursor to refrigerants and in turn PTFE. Chloroform is a trihalomethane that serves as a powerful anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested. Chloroform was used as an anesthetic between the 19th century and the first half of the 20th century. It is miscible with many solvents but it is only very slightly soluble in water.

<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<span class="mw-page-title-main">3-Pentanone</span> Chemical compound

3-Pentanone is a simple, symmetrical dialkyl ketone. It is a colorless liquid ketone with an odor like that of acetone. It is soluble in about 25 parts water, but miscible with organic solvents.

<span class="mw-page-title-main">Acetone</span> Organic compound ((CH3)2CO); simplest ketone

Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

<span class="mw-page-title-main">Proton nuclear magnetic resonance</span> NMR via protons, hydrogen-1 nuclei

Proton nuclear magnetic resonance is the application of nuclear magnetic resonance in NMR spectroscopy with respect to hydrogen-1 nuclei within the molecules of a substance, in order to determine the structure of its molecules. In samples where natural hydrogen (H) is used, practically all the hydrogen consists of the isotope 1H.

Hydrogen–deuterium exchange is a chemical reaction in which a covalently bonded hydrogen atom is replaced by a deuterium atom, or vice versa. It can be applied most easily to exchangeable protons and deuterons, where such a transformation occurs in the presence of a suitable deuterium source, without any catalyst. The use of acid, base or metal catalysts, coupled with conditions of increased temperature and pressure, can facilitate the exchange of non-exchangeable hydrogen atoms, so long as the substrate is robust to the conditions and reagents employed. This often results in perdeuteration: hydrogen-deuterium exchange of all non-exchangeable hydrogen atoms in a molecule.

Deuterated chloroform, also known as chloroform-d, is the organic compound with the formula CDCl3 or C2HCl3. Deuterated chloroform is a common solvent used in NMR spectroscopy. The properties of CDCl3 and ordinary CHCl3 (chloroform) are virtually identical.

<span class="mw-page-title-main">Deuterated benzene</span> Chemical compound

Deuterated benzene (C6D6) is an isotopologue of benzene (C6H6) in which the hydrogen atom ("H") is replaced with deuterium (heavy hydrogen) isotope ("D").

<span class="mw-page-title-main">Deuterated methanol</span> Chemical compound

Deuterated methanol (CD3OD), is a form (called an isotopologue) of methanol (CH3OH) in which the hydrogen atoms ("H") are replaced with deuterium (heavy hydrogen) isotope ("D"). Deuterated methanol is a common solvent used in NMR spectroscopy.

Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.

<span class="mw-page-title-main">Deuterated DMSO</span> Chemical compound

Deuterated DMSO, also known as dimethyl sulfoxide-d6, is an isotopologue of dimethyl sulfoxide (DMSO, (CH3)2S=O)) with chemical formula ((CD3)2S=O) in which the hydrogen atoms ("H") are replaced with their isotope deuterium ("D"). Deuterated DMSO is a common solvent used in NMR spectroscopy.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of propan-1-ol and ethyl methyl ether. They all have the formula C3H8O.

<span class="mw-page-title-main">Deuterated solvent</span>

Deuterated solvents are a group of compounds where one or more hydrogen atoms are substituted by deuterium atoms.

Deuterated dichloromethane (CD2Cl2) is a form (called an isotopologue) of dichloromethane (DCM, CH2Cl2) in which the hydrogen atoms ("H") are replaced with deuterium (heavy hydrogen) isotope ("D"). Deuterated DCM is not a common solvent used in NMR spectroscopy as it is expensive compared to deuterated chloroform.

<span class="mw-page-title-main">Acetone azine</span> Chemical compound

Acetone azine is the simplest ketazine. It is an intermediate in some hydrazine manufacturing processes.

<span class="mw-page-title-main">Methoxyamine</span> Chemical compound

Methoxyamine is the organic compound with the formula CH3ONH2. Also called O-methylhydroxylamine, it is a colourless volatile liquid that is soluble in polar organic solvent and in water. It is a derivative of hydroxylamine with the hydroxyl hydrogen replaced by a methyl group. Alternatively, it can be viewed as a derivative of methanol with the hydroxyl hydrogen replaced by an amino group. It is an isomer of N-methylhydroxylamine and aminomethanol. It decomposes in an exothermic reaction (-56 kJ/mol) to methane and azanone unless stored as a hydrochloride salt.

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.