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1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium tetrafluoroborate

1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium tetrafluoroborate

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Catalog Number

ACM245679189-3

Product Name

Structure

CAS

245679-18-9

Product Overview
Usage

Synonyms

1,3-Dimesityl-4,5-Dihydro-1H-Imidazol-3-Ium Tetrafluoroborate

IUPAC Name

1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-1-ium;tetrafluoroborate

Molecular Weight

394.26

Molecular Formula

C21H27BF4N2

Canonical SMILES

[B-](F)(F)(F)F.CC1=CC(=C(C(=C1)C)N2CC[N+](=C2)C3=C(C=C(C=C3C)C)C)C;

InChI

VNRDQIOMNLIVQJ-UHFFFAOYSA-N

InChI Key

InChI=1S/C21H27N2.BF4/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;2-1(3,4)5/h9-13H,7-8H2,1-6H3;/q+1;-1

Melting Point

290-296 °C

Purity

98%

Appearance

Off-white powder

Complexity

398

Covalently-Bonded Unit Count

Exact Mass

394.22g/mol

H-Bond Acceptor

Heavy Atom Count

Isomeric SMILES

[B-](F)(F)(F)F.CC1=CC(=C(C(=C1)C)N2CC[N+](=C2)C3=C(C=C(C=C3C)C)C)C

Monoisotopic Mass

394.22g/mol

Rotatable Bond Count

Topological Polar Surface Area

6.2A^2

Application

1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium tetrafluoroborate is a versatile ligand used to facilitate various catalytic reactions. It plays a crucial role in the ruthenium-catalyzed selective reduction of nitriles to primary amines, enabling efficient synthesis of these compounds. Additionally, it serves as a ligand for nickel-catalyzed [2+2+2] cycloaddition of arynes and unactivated alkenes, contributing to the formation of complex molecular structures. Furthermore, this compound is employed in copper-catalyzed reactions, including [3+2] cycloaddition of azides and alkynes under mild conditions and the direct aryl quaternization of N-substituted imidazoles to form imidazolium salts. It also aids in the copper-catalyzed silylation of allenes, illustrating its broad application across various chemical transformations.

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CAS
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Purity
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245679-18-9
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98%
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