286014-42-4

Basic information

• Product Name: 1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate
• Synonyms: N,N'-(ADAMANTYL)DIHYDROIMIDAZOLIUM TETRAFLUOROBORATE;N,N'-(ADAMANTYL)IMIDAZOLIUM TETRAFLUOROBORATE;1,3-DIADAMANTYL-IMIDAZOLIUM TETRAFLUOROBORATE;1,3-BIS(1-ADAMANTYL)IMIDAZOLINIUM TETRAFLUOROBORATE;1,3-BIS(1-ADAMANTYL)IMIDAZOLIUM TETRAFLUOROBORATE;1,3-BIS(TRICYCLO[3.3.1.1(3,7)]DEC-1-YL)-1H-IMIDAZOLIUM TETRAFLUOROBORATE;1,3-BIS(1-ADAMANTYL)IMIDAZOLIUM TETRAFL&;1,3-Di(1-adamantyl)imidazolium Tetrafluoroborate
• CAS NO: 286014-42-4
• Molecular Formula: C23H33BF4N2
• Molecular Weight: 424.33
• Product Categories: B (Classes of Boron Compounds);Imidazolium Compounds;Ligands;N-Heterocyclic Carbene Ligands;Synthetic Organic Chemistry;Tetrafluoroborates;Achiral Nitrogen;NHC
• Mol File: 286014-42-4.mol

Chemical Properties

• Melting Point: 277-282 °C
• Appearance: White to pale brown/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate(286014-42-4)
• EPA Substance Registry System: 1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate(286014-42-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 1759
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 286014-42-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H33N2.BF4/c1-2-25(23-12-19-6-20(13-23)8-21(7-19)14-23)15-24(1)22-9-16-3-17(10-22)5-18(4-16)11-22;2-1(3,4)5/h1-2,15-21H,3-14H2;/q+1;-1

Upstream product

• 50-00-0 formaldehyd 
• 131543-46-9 Glyoxal 
• 768-94-5 1-Adamantanamine 

Downstream Products

• 131042-77-8 IAd 

Relevant articles and documents

Tuning the Reactivity of a Heterogeneous Catalyst using N-Heterocyclic Carbene Ligands for C?H Activation Reactions

We report the dramatic impact of the addition of N-heterocyclic carbenes (NHCs) on the reactivity and selectivity of heterogeneous Ru catalysts in the context of C?H activation reactions. Using a simple and robust method, we prepared a series of new air-stable catalysts starting from commercially available Ru on carbon (Ru/C) and differently substituted NHCs. Associated with C?H deuteration processes, depending on Ru/C-NHC ratios, the chemical outcome can be controlled to a large extent. Indeed, tuning the reactivity of the Ru catalyst with NHC enabled: 1) increased chemoselectivity and the regioselectivity for the deuteration of alcohols in organic media; 2) the synthesis of fragile pharmaceutically relevant deuterated heterocycles (azine, purine) that are otherwise completely reduced using unmodified commercial catalysts; 3) the discovery of a novel reactivity for such heterogeneous Ru catalysts, namely the selective C-1 deuteration of aldehydes.

Iron-Catalyzed Cross-Coupling Reactions of Arylmagnesium Reagents with Aryl Chlorides and Tosylates: Influence of Ligand Structural Parameters and Identification of a General N-Heterocyclic Carbene Ligand

A systematic evaluation of N-heterocyclic carbene ligands in the iron-catalyzed cross-coupling reactions of aryl chlorides and arylmagnesium reagents is performed. There is no clear correlation between the donor strength of the N-heterocyclic carbene and the reaction outcome. Instead, the highest yields of the desired biaryl product are obtained with sterically demanding ligands possessing large %Vbur values. Through this study, SIPrNap has been identified as an efficient and general ligand for the coupling of both aryl chlorides and tosylates.

Regioselective hydrocarbamoylation of 1-alkenes

Nickel/Lewis acid cooperative catalysis derived from [Ni(cod)2], AlEt3, and N-heterocyclic carbene (NHC) effects highly regioselective hydrocarbamoylation of 1-alkenes. Variously substituted formamides and 1-alkenes can be employed to give a range of linear alkanamides regioselectively.

Thieme Chemistry Journal awardees - Where are they now? Synthesis of diamantane-derived N-heterocyclic carbenes and applications in catalysis

Novel diamantyl-substituted imidazolium salts have been synthesized, characterized and, in addition, analyzed by single-crystal structural analysis. The corresponding NHCs (a-IDAd and m-IDAd) have been prepared in solution and have been characterized by N