Deuterated benzene

Deuterated benzene  | Kekulé, skeletal formula of deuterated benzene | Spacefill model of deuterated benzene

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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

EC Number |

* 214-061-8

PubChem CID

* 71601

UN number | 1114

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
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 pictograms |
GHS Signal word | Danger

GHS hazard statements

| H225, H304, H315, H319, H340, H350, H372

GHS precautionary statements

| P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P301+310, P302+352, P303+361+353, P305+351+338, P308+313, P314, P321, P331, P332+313, P337+313, P362, P370+378
NFPA 704 (fire diamond)  |

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

Tracking categories (test):

* SizeSet

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. pp. 1142. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
2. ↑ "Benzene-d6". https://www.sigmaaldrich.com/CA/en/product/aldrich/151815?context=product.
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". Organometallics 29 (9): 2176–2179. doi:10.1021/om100106e. https://authors.library.caltech.edu/18475/2/om100106e_si_001.pdf.

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Deuterated NMR Solvents

Deuterated|

* Deuterated acetone \- (CD3)2C=O
* Deuterated benzene \- C6D6
* Deuterated chloroform \- CDCl3
* Deuterated dichloromethane \- CD2Cl2
* Deuterated DMF \- (CD3)2NCOD
* Deuterated DMSO \- (CD3)2S=O
* Deuterated ethanol \- C2D5OD
* Deuterated methanol \- CD3OD
* Deuterated THF \- (C4D8)O
* Deuterated water \- D2O

Reference

1H and 13C chemical shifts

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Deuterated_benzene&oldid=248211"
*[CID]: Compound ID
*[H225]: Highly flammable liquid and vapour
*[H304]: May be fatal if swallowed and enters airways
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H340]: May cause genetic defects
*[H350]: May cause cancer
*[H372]: Causes damage to organs through prolonged or repeated exposure
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P281]: Use personal protective equipment as required
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P314]: Get Medical advice/attention if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P331]: Do NOT induce vomiting
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P370+378]: In case of fire: Use … for extinction
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