Deuterated benzene

Deuterated benzene

Kekulé, skeletal formula of deuterated benzene Spacefill model of deuterated benzene
Ball and stick model of deuterated benzene
Names
Preferred IUPAC name (2H6)Benzene [1]
Identifiers
CAS Number	1076-43-3  Y
3D model (JSmol)	Interactive image
Beilstein Reference	1905426
ChEBI	CHEBI:193039
ChemSpider	64671  Y
ECHA InfoCard	100.012.784
EC Number	214-061-8
PubChem CID	71601
UN number	1114
CompTox Dashboard (EPA)	DTXSID7037769
InChI InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H/i1D,2D,3D,4D,5D,6D Y Key: UHOVQNZJYSORNB-MZWXYZOWSA-N Y
SMILES [2H]c1c([2H])c([2H])c([2H])c([2H])c1[2H]
Properties
Chemical formula	C62H6 or C6D6
Molar mass	84.1488 g mol−1
Density	0.950 g cm−3
Melting point	7 °C; 44 °F; 280 K
Boiling point	79 °C; 174 °F; 352 K
Thermochemistry
Heat capacity (C)	152.46 J K−1 mol−1
Hazards
GHS labelling:
Pictograms
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)	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 [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

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. ^[2]

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. ^[3]

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:

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.