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

Catalog Number
ACM173035115-1
Product Name
1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene
Structure
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CAS
173035-11-5
  • Product Overview
  • Usage
Synonyms
1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydro-2H-imidazol-1-ium-2-ide; 1,3-Dimesitylimidazolidin-2-ylidene; IMesH2
IUPAC Name
1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-2H-imidazol-1-ium-2-ide
Molecular Weight
306.44
Molecular Formula
C21H26N2
Canonical SMILES
CC1=CC(=C(C(=C1)C)N2CC[N+](=[C-]2)C3=C(C=C(C=C3C)C)C)C;
InChI
LSMWOQFDLBIYPM-UHFFFAOYSA-N
InChI Key
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
Melting Point
79-85 °C
Purity
98%
Appearance
Solid
Complexity
379
Covalently-Bonded Unit Count
1
Exact Mass
306.21g/mol
H-Bond Acceptor
1
Heavy Atom Count
23
Isomeric SMILES
CC1=CC(=C(C(=C1)C)N2CC[N+](=[C-]2)C3=C(C=C(C=C3C)C)C)C
Monoisotopic Mass
306.21g/mol
Rotatable Bond Count
2
Topological Polar Surface Area
6.2A^2
Application
1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene serves as a versatile ligand designed to facilitate the copper-catalyzed regioselective formation of tri- and tetrasubstituted vinylboronates in air. This product harnesses its potential as a robust component in various catalytic processes, including acting as a ligand for highly active ruthenium catalysts in the hydrogenation of olefins and serving as an electrophilic phosphonium cation in reactions for ketone catalytic hydrodeoxygenation and hydrosilylation. Additionally, it plays a critical role in the selective activation of fluoroalkenes, leading to the production of N-heterocyclic fluoroalkenes and polyfluoroalkenyl imidazolium salts, showcasing its diverse applicability in synthetic chemistry.
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