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

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

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Catalog Number

ACM173035115-1

Product Name

Structure

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

Exact Mass

306.21g/mol

H-Bond Acceptor

Heavy Atom Count

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

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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CAS
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Purity
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173035-11-5
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98%
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1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, min. 98% (141556-42-5)
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