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1,3-Di-tert-butylimidazol-2-ylidene / 1 g

Synonym: ItBu; 1,3-Di-tert-butylimidazol-2-ylidene; 1,3-ditert-butyl-2H-imidazol-1-ium-2-ide; 1,3-Di-tert-butyl-1H-imidazol-3-ium-2-ide; 1,3-DI-TERT-BUTYLIMIDAZOL-1-IUM-2-IDE
Molecular Weight: 180.29
SKU: MND-190026
CAS Number: 157197-53-0
MDL number: MFCD03788921
Packing size: 1 g  



Safety Information


Hazard Statements

H315
H319
H335
H228

Precautionary Statements

P210
P280
P264
P501
P305 + P351 + P338
P261
P271
P240
P241
P405
P302 + P352
P362 + P364
P403 + P233
P370 + P378
P304 + P340
P321
P264 + P265
P319
P332 + P317
P337 + P317

Pictograms



Properties

Signal WordDanger

 Product Description

1,3-Di-tert-butylimidazol-2-ylidene is a substituted imidazol-2-ylidene bearing two tert-butyl groups. Imidazol-2-ylidenes are part of a broader class of compounds known as N-heterocyclic carbenes (NHCs), which are recognized for their ability to form strong bonds with metals, making them valuable ligands in organometallic chemistry. The presence of bulky tert-butyl groups enhances the steric hindrance around the carbene carbon, influencing its reactivity and stability. These features position 1,3-Di-tert-butylimidazol-2-ylidene as a potentially useful building block in the synthesis of complexes with tailored electronic and steric properties.

 

Application

In practical applications, 1,3-Di-tert-butylimidazol-2-ylidene could be utilized as a ligand in the preparation of metal complexes for catalysis, particularly in homogeneous catalysis where its NHC backbone can stabilize reactive metal centers. Its sterically demanding substituents may also influence the selectivity of catalyzed reactions, making it of interest in the development of new catalysts for challenging transformations. Additionally, its basicity and nucleophilicity suggest potential applications in organic synthesis, where it could serve as a directing group or activating agent in reaction sequences.

 

 

Articles:

- Basicity of a Stable Carbene, 1,3-Di-tert-butylimidazol-2-ylidene, in THF

Publication Date: April 25, 2002

Yeong-Joon Kim and Andrew Streitwieser

https://doi.org/10.1021/ja025628j

 

- Preparation of Monomeric [LAl(NH2)2]—A Main-Group Metal Diamide Containing Two Terminal NH2 Groups

Publication Date: 06 April 2004

Vojtech Jancik Dipl.-Chem., Leslie W. Pineda Dipl.-Chem., Jiri Pinkas Prof. Dr., Herbert W. Roesky Prof. Dr., Dante Neculai Dr., Ana M. Neculai Dr., Regine Herbst-Irmer Dr.

https://doi.org/10.1002/anie.200353541

 

- Ruthenium Hydride Complexes of 1,2-Dicyclohexylimidazol-2-ylidene

Publication Date: October 21, 2005

Suzanne Burling, Gabriele Kociok-Köhn, Mary F. Mahon, Michael K. Whittlesey, and Jonathan M. J. Williams

https://doi.org/10.1021/om050600c