CAS 1100-88-5 Benzyltriphenylphosphonium chloride

Synonyms

Triphenyl(phenylmethyl)-phosphoniuchloride

IUPAC Name

benzyl(triphenyl)phosphanium;chloride;

Molecular Weight

388.87

Molecular Formula

C25H22ClP

Canonical SMILES

C1=CC=C(C=C1)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Cl-];

InChI

InChI=1S/C25H22P.ClH/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1;

InChI Key

USFRYJRPHFMVBZ-UHFFFAOYSA-M;

Storage

Store at <= 20°C.

Complexity

347

Covalently-Bonded Unit Count

EC Number

214-154-3

Exact Mass

388.115g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

388.115g/mol

NSC Number

116712

Physical State

Solid

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

Benzyltriphenylphosphonium chloride serves as a versatile reagent in organic synthesis, primarily functioning as a Wittig reagent and phase transfer catalyst. As a white to off-white powder, it is highly soluble in water and polarizable solvents. Its applications include the production of fluoroelastomers and printing inks, and it is instrumental in synthesizing stabilized phosphonium ylides with saturated oxygen heterocycles. The compound also plays a crucial role in creating novel substituted cis-stilbene derivatives with antimicrobial properties. Additionally, it acts as a reactant in diverse syntheses, such as platinum chloro-tetrazole complexes, trans-stilbenes, and cinnamates through Wittig olefination, as well as achiral N-hydroxyformamide inhibitors targeting ADAM-TS4 and ADAM-TS5 for osteoarthritis treatment. The reagent is essential in producing pentiptycenes for light-driven molecular brakes and aiding in the formation of archipelago structures for petroleum asphaltene development. Moreover, benzyltriphenylphosphonium chloride is used as a crosslinking agent in crafting tube-like natural halloysite/fluoroelastomer nanocomposites.

January 21, 2025

Essential Reagent for Synthetic Chemistry

Benzyltriphenylphosphonium chloride proved invaluable in our lab for Wittig olefination. Its high solubility streamlined the synthesis of trans-stilbenes, enhancing our research efficiency. A must-have for organic synthesis projects!