Tricyclohexylphosphine tetrafluoroborate

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Catalog Number
ACM58656045-2
Product Name
Tricyclohexylphosphine tetrafluoroborate
Structure
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CAS
58656-04-5
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Synonyms
RTR-020374; CT-797; MFCD03840580; ANW-33005; tricyclohexylphosphoniumtetrafluoroborate; SC-44376; C18H34BF4P; M-4781; AK-85999; BCP21733;
IUPAC Name
tricyclohexylphosphanium;tetrafluoroborate;
Molecular Weight
368.247g/mol
Molecular Formula
C18H34BF4P;
Canonical SMILES
[B-](F)(F)(F)F.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3;
InChI
InChI=1S/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;
InChI Key
MYSMMEUXKHJYKH-UHFFFAOYSA-O;
Complexity
221
Covalently-Bonded Unit Count
2
Exact Mass
368.243g/mol
H-Bond Acceptor
5
Heavy Atom Count
24
Monoisotopic Mass
368.243g/mol
Rotatable Bond Count
3
Topological Polar Surface Area
0A^2
Application
Tricyclohexylphosphine tetrafluoroborate (PCy3·HBF4) serves a versatile role in modern chemistry, acting as a non-pyrophoric and air-stable phosphine ligand crucial for various stoichiometric and catalytic processes. Its primary purpose is to facilitate cross-coupling reactions, particularly enhancing the reactivity of palladium-catalyzed Suzuki-Miyaura reactions between MIDA boronates and less activated alkenyl tosylates. This compound is also pivotal in the synthesis of significant pharmaceutical intermediates, such as the JAK2 inhibitor BMS-911543, a potential treatment for myeloproliferative disorders, and in the preparation of Lapatinib intermediates. Additionally, it assists in forming C-homoaporphine alkaloids using microwave-assisted direct-arylation and synthesizing conductive materials like PFDBSO3H to enhance the performance of PEDOT films. Overall, Tricyclohexylphosphine tetrafluoroborate is an affordable and efficient ligand that replaces neat phosphine in diverse synthetic applications.
January 9, 2025

Reliable and Versatile Reagent for Cross-Coupling

I used Tricyclohexylphosphine tetrafluoroborate in a Suzuki reaction to enhance palladium-catalyzed processes. Its air stability and cost-effectiveness were impressive. It significantly improved our synthetic outcomes in JAK2 inhibitor research. Highly recommended!

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