SIMes

Names
IUPAC name

1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene

Other names

IMesH2, H2IMes, 1,3-Dimesityl-imidazol-4,5-dihydro-2-ylidene

Identifiers

CAS Number

* 173035-11-5

3D model (JSmol)

* Interactive image

ChemSpider |

* 9403305

PubChem CID

* 11228257

SMILES

* Cc1cc(C)c(c(C)c1)N2CCN([C]2)c3c(C)cc(C)cc3C

Properties

Chemical formula

| C21H26N2
Molar mass | 306.453 g·mol−1
Melting point |  79 to 85 °C (174 to 185 °F; 352 to 358 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

SIMes (or H2Imes) is an N-heterocyclic carbene. It is a white solid that dissolves in organic solvents. The compound is used as a ligand in organometallic chemistry. It is structurally related to the more common ligand IMes but with a saturated backbone (the S of SIMes indicates a saturated backbone). It is slightly more flexible and is a component in Grubbs II.[1] It is prepared by alkylation of trimethylaniline by dibromoethane followed by ring closure and dehydrohalogenation.[2]

## References

1. ↑ Nolan, Steven P. (2006). N-Heterocyclic Carbenes in Synthesis. Wiley-VCH. ISBN 978-3-527-60940-6.
2. ↑ "Synthesis of 1,3–bis(2,4,6–trimethylphenyl)–imidazolinium salts : SIMes.HCl, SIMes.HBr, SIMes.HBF4 and SIMes.HPF6. : Protocol Exchange" (in en). http://www.nature.com/protocolexchange/protocols/2488#/procedure.

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*[CID]: Compound ID