58656-04-5 Usage
Uses
1. Used in Pharmaceutical Synthesis:
Tricyclohexylphosphonium tetrafluoroborate is used as a reagent for the synthesis of potent JAK2 inhibitor BMS-911543, which is a potential treatment for myeloproliferative disorders. It is also used in the preparation of Lapatinib intermediate via arylation of furfural with bromochlorofluorobenzyloxyphenylquinazolinamine and in the structure-activity relationships of carboline and carbazole derivatives as ATP-competitive kinesin spindle protein inhibitors.
2. Used in Suzuki Reaction:
Tricyclohexylphosphine tetrafluoroborate is used as a ligand to improve the reactivity of palladium-catalyzed Suzuki-Miyaura cross-coupling reaction between MIDA boronates and less activated alkenyl tosylates, which is a crucial process in the synthesis of various organic compounds.
3. Used in C-homoaporphine Alkaloids Synthesis:
Tricyclohexylphosphonium tetrafluoroborate is used as a ligand for preparing C-homoaporphine alkaloids via microwave-assisted direct-arylation, which is an important class of compounds with potential applications in the pharmaceutical industry.
4. Used in Conductive Polymers:
Tricyclohexylphosphine tetrafluoroborate is used in the synthesis of poly-[9,9-bis(3-propylamide-2-methylpropyl sulfonic acid) fluorene]-co-(4,4′-diphenyl) (PFDBSO3H), which can be employed as a template and doping agent for enhancing the conductivity of poly(3,4-ethylenedioxythiophene) (PEDOT) films, a crucial material in the development of organic electronic devices.
Reactions
Non-pyrophoric, air-stable derivative suitable as a replacement for the neat phosphine in a variety of stoichiometric and catalytic processes.
Check Digit Verification of cas no
The CAS Registry Mumber 58656-04-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,6,5 and 6 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 58656-04:
(7*5)+(6*8)+(5*6)+(4*5)+(3*6)+(2*0)+(1*4)=155
155 % 10 = 5
So 58656-04-5 is a valid CAS Registry Number.
InChI:InChI=1/C18H33P.BF4/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;2-1(3,4)5/h16-18H,1-15H2;/q;-1/p+1
58656-04-5Relevant articles and documents
Vinyl and carbene ruthenium(II) complexes from hydridoruthenium(II) precursors
Jung, Stefan,Brandt, Carsten D.,Wolf, Justin,Werner, Helmut
, p. 375 - 383 (2007/10/03)
The reactions of the hydrido compounds [RuHCl(CO)(L)2] {L = PiPr3 (1), PCy3 (2)} with HC≡CR (R = H, Ph, tBu) afforded by insertion of the alkyne into the Ru-H bond the corresponding vinyl complexes [RuCl(CH=CHR)-(CO)(L)su
Acid-promoted homogeneous hydrogenation of alkenes catalyzed by the ruthenium-hydride complex (PCy3)2(CO)(Cl)RuH: Evidence for the formation of 14-electron species from the selective entrapment of the phosphine ligand
Yi,Lee,He,Rheingold,Lam,Concolino
, p. 2909 - 2915 (2008/10/08)
The addition of 1.0 equiv of HBF4·OEt2 led to a ca. 2-3-fold increase in the catalyst activity of (PCy3)2(CO)(Cl)RuH (1a) toward the hydrogenation of alkenes. The stoichiometric reaction of 1a with HBF4·OEt2 produced a 1:3.5 mixture of the new ruthenium-hydride species 2 and Cy3PH+BF4-. The catalyst activity of the isolated 2/Cy3PH+ mixture was found to be similar to 1a/HBF4·OEt2. The complex 2 slowly decomposed in C6H6 solution to give a novel tetrameric complex 3. The treatment of 1a with HBF4·OEt2 in CH3CN led to the selective formation of the monophosphine species 4, which was converted to the stable complex 5 upon treatment with excess PPh3. The reaction of 1a with a weak acid, HSiCl3, led to the formation of the anionic silyl complex 7. The structures of 3, 5, and 7 were determined by X-ray crystallography. The formation of η2-H2 complex 8 was observed by NMR at low temperature. These results suggested that the 14-electron species [(PCy3)(CO)RuHCl], generated from the selective entrapment of the phosphine ligand, is the key species involved in the catalytic hydrogenation reaction.
