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Deuterated benzene

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Deuterated benzene
Kekulé, skeletal formula of deuterated benzene
Kekulé, skeletal formula of deuterated benzene
Spacefill model of deuterated benzene
Spacefill model of deuterated benzene
Ball and stick model of deuterated benzene
Names
Preferred IUPAC name (H6)Benzene
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1905426
ChEBI
ChemSpider
ECHA InfoCard 100.012.784 Edit this at Wikidata
EC Number
  • 214-061-8
PubChem CID
UN number 1114
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H/i1D,2D,3D,4D,5D,6DKey: UHOVQNZJYSORNB-MZWXYZOWSA-N
SMILES
  • c1c()c()c()c()c1
Properties
Chemical formula C6H6 or C6D6
Molar mass 84.1488 g mol
Density 0.950 g cm
Melting point 7 °C; 44 °F; 280 K
Boiling point 79 °C; 174 °F; 352 K
Thermochemistry
Heat capacity (C) 152.46 J K mol
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H225, H304, H315, H319, H340, H350, H372
Precautionary statements P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P308+P313, P314, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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
2 3 0
Flash point −11 °C (12 °F; 262 K)
Related compounds
Related compounds Benzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
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").

Properties

The properties of deuterated benzene are very similar to those of normal benzene, however, the increased atomic weight of deuterium relative to protium means that the melting point of C6D6 is about 1.3 °C higher than that of the nondeuterated analogue. The boiling points of both compounds, however, are the same: 80 °C.

Applications

Deuterated benzene is a common solvent used in NMR spectroscopy. It is widely used for taking spectra of organometallic compounds, which often react with the cheaper deuterated chloroform.

A slightly more exotic application of C6D6 is in the synthesis of molecules containing a deuterated phenyl group. Deuterated benzene will undergo all the same reactions its normal analogue will, just a little more slowly due to the kinetic isotope effect. For example, deuterated benzene could be used in the synthesis of deuterated benzoic acid, if desired: Synthesis of deuterated benzoic acid from deutrated benzene

Many simple monosubstituted aromatic compounds bearing the deuterated phenyl (C6D5) group may be purchased commercially, such as aniline, acetophenone, nitrobenzene, bromobenzene, and more.

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1142. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. "Benzene-d6". sigmaaldrich.com. Retrieved 4 August 2023.
  3. Fulmer, Gregory R.; Miller, Alexander J. M.; Sherden, Nathaniel H.; Gottlieb, Hugo E.; Nudelman, Abraham; Stoltz, Brian M.; Bercaw, John E.; Goldberg, Karen I. (2010). "NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist" (PDF). Organometallics. 29 (9): 2176–2179. doi:10.1021/om100106e.
Deuterated NMR solvents
Reference
1H and 13C chemical shifts


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