1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate

Base Information

• Chemical Name: 1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate
• CAS No.: 286014-42-4
• Molecular Formula: BF₄*C₂₃H₃₃N₂
• Molecular Weight: 424.333
• European Community (EC) Number: 625-289-6
• DSSTox Substance ID: DTXSID50584749
• Mol file: 286014-42-4.mol

Synonyms:286014-42-4;1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate;1,3-Di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate;1,3-Di(1-adamantyl)imidazolium Tetrafluoroborate;1,3-bis(1-adamantyl)imidazol-1-ium;tetrafluoroborate;1H-Imidazolium, 1,3-bis(tricyclo[3.3.1.13,7]dec-1-yl)-, tetrafluoroborate(1-) (1:1);MFCD04973311;IAd.HBF4;1,3-Diadamantyl-imidazolium tetrafluoroborate;SCHEMBL589769;C23H33BF4N2;DTXSID50584749;AKOS015832932;AKOS037644063;AKOS040767247;AS-44296;1,3-Diadamantylimidazoliumtetrafluoroborate;D3621;1,3-DIADAMANTYL-IMIDAZOLIUMTETRAFLUOROBORATE;1,3-Di(adamantan-1-yl)-1H-imidazol-3-iumtetrafluoroborate;1,3-Di(tricyclo[3.3.1.1~3,7~]decan-1-yl)-1H-imidazol-3-ium tetrafluoroborate

Chemical Property of 1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate

Chemical Property:

• Melting Point: 277-282 ºC
• PSA: 8.81000
• LogP: 5.92620
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 424.2672919
• Heavy Atom Count: 30
• Complexity: 467

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3-Di(1-adamantyl)imidazolium Tetrafluoroborate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [B-](F)(F)(F)F.C1C2CC3CC1CC(C2)(C3)N4C=C[N+](=C4)C56CC7CC(C5)CC(C7)C6

Technology Process of 1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate

There total 3 articles about 1,3-Bis(1-adamantyl)imidazolium tetrafluoroborate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Glyoxal (131543-46-9,107-22-2) + 1-Adamantanamine (768-94-5) → 1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate (286014-42-4)

Guidance literature:

formaldehyd; 1-Adamantanamine; In chloroform; at 20 ℃; for 1h;

Glyoxal; 1-Adamantanamine; With tetrafluoroboric acid; In chloroform; water; at 0 - 60 ℃;

DOI:10.1246/cl.2012.298

Reference yield: 55.0%

tetrafluoroboric acid + formaldehyd (50-00-0,30525-89-4,61233-19-0) + Glyoxal (131543-46-9,107-22-2) + 1-Adamantanamine (768-94-5) → 1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate (286014-42-4)

Guidance literature:

formaldehyd; 1-Adamantanamine; In toluene; at 0 - 20 ℃; for 1h;

tetrafluoroboric acid; In water; toluene; Cooling;

Glyoxal; In water; toluene; at 60 ℃; for 36h;

DOI:10.1002/anie.202009258

Reference yield:

1,3-di(1-adamantyl)imidazolium iodide → 1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate (286014-42-4)

Guidance literature:

With silver tetrafluoroborate; In acetonitrile;

DOI:10.1021/acs.organomet.7b00180

upstream raw materials:

formaldehyd

Glyoxal

1-Adamantanamine

Downstream raw materials:

IAd

Refernces

• 1、 Wu, Wenqin,Teng, Qiaoqiao,Chua, Yi-Yuan,Huynh, Han Vinh,Duong, Hung A.. "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". supporting information. p. 2293 - 2297. Retrieved 2017/06/30.
• 2、 Richter, Heinrich,Schwertfeger, Hartmut,Schreiner, Peter R.,Fr?hlich, Roland,Glorius, Frank. "Thieme Chemistry Journal awardees - Where are they now? Synthesis of diamantane-derived N-heterocyclic carbenes and applications in catalysis". experimental part. p. 193 - 197. Retrieved 2009/06/23.