SIMes

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;
CompTox Dashboard (EPA)	DTXSID20459319 ;
	InChI InChI=1S/C21H26N2/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6/h9-12H,7-8H2,1-6H3 Key: LSMWOQFDLBIYPM-UHFFFAOYSA-N;
	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

↑ Nolan, Steven P. (2006). N-Heterocyclic Carbenes in Synthesis. Wiley-VCH. ISBN 978-3-527-60940-6.
↑ "Synthesis of 1,3–bis(2,4,6–trimethylphenyl)–imidazolinium salts : SIMes.HCl, SIMes.HBr, SIMes.HBF₄ and SIMes.HPF₆. : Protocol Exchange". www.nature.com. 10 October 2012. Retrieved 2017-09-25.

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[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". www.nature.com. 10 October 2012. Retrieved 2017-09-25.

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References