CAS 13423-48-8 n-Heptyl triphenylphosphonium bromide

Synonyms

I14-45399; N-HEPTYL TRIPHENYL PHOSPHONIUMBROMIDE; MFCD00050249 (97%); DB-042221; KS-00000Z5V; heptyl(triphenyl)phosphanium bromide; AKOS015833040; C7H15PPh3Br; n-Heptyl triphenylphosphonium bromide; heptyltriphenylphosphanium bromide;

IUPAC Name

heptyl(triphenyl)phosphanium;bromide;

Molecular Weight

441.393g/mol

Molecular Formula

C25H30BrP;

Canonical SMILES

CCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-];

InChI

InChI=1S/C25H30P.BrH/c1-2-3-4-5-15-22-26(23-16-9-6-10-17-23,24-18-11-7-12-19-24)25-20-13-8-14-21-25;/h6-14,16-21H,2-5,15,22H2,1H3;1H/q+1;/p-1;

InChI Key

WCZSOHSGMBVYFW-UHFFFAOYSA-M;

Complexity

313

Covalently-Bonded Unit Count

EC Number

236-539-5

Exact Mass

440.127g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

440.127g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

n-Heptyl triphenylphosphonium bromide, a white fine crystalline powder, is a versatile reagent used in several specialized chemical reactions. It plays a crucial role in the stereospecific rearrangement of epoxides to quaternary carbaldehydes, aiding in precise structural transformations. This compound is instrumental in synthesizing the male pheromone for certain termite species, Zootermopsis, demonstrating its application in entomological studies. Furthermore, it facilitates regio- and stereoselective TEMPO oxidation, an important process for selective oxidation reactions. n-Heptyl triphenylphosphonium bromide also supports the diastereoselective synthesis of climacostol, a compound with potential antitumor activity, indicating its relevance in pharmaceutical research. Additionally, it is employed in the enantioselective synthesis of chiral vinylphosphonate and its analogs, which are related to the immunosuppressive agent FTY720, enhancing its significance in medicinal chemistry. Lastly, this compound is used in preparing embelin derivatives that exhibit XIAP inhibitory and anticancer activity, highlighting its importance in developing therapeutic agents.

February 7, 2025

Efficient and Versatile Chemical Reagent for Research

Using Alfa Chemistry's n-Heptyl triphenylphosphonium bromide in stereospecific epoxide rearrangements yielded precise outcomes. Its fine crystalline form ensured ease in handling and exceptional reliability in synthetic and regioselective processes. Highly recommended for accurate research applications.