CAS 39319-11-4 Triphenylphosphine, polymer-bound

Synonyms

Triphenylphosphine, flakes; CHEMBL1448331; 39319-11-4; P(C6H5)3; 58079-51-9; triphenyl phosphin; NCGC00259663-01; ZX-AT007677; FT-0689298; Triphenylphosphine, powder;

IUPAC Name

triphenylphosphane;

Molecular Weight

262.292g/mol

Molecular Formula

C18H15P;(C6H5)3P;C18H15P;

Canonical SMILES

C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3;

InChI

InChI=1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H;

InChI Key

RIOQSEWOXXDEQQ-UHFFFAOYSA-N;

Melting Point

176 ° F (NTP, 1992);80.0°C;80.5 DEG C;80 °C;

Density

1.194 at 77 ° F (NTP, 1992);1.075 @ 80 DEG C/4 DEG C;1.1 g/cm³;

Solubility

Insoluble (NTP, 1992);FREELY SOL IN ETHER; SOL IN BENZENE, CHLOROFORM, GLACIAL ACETIC ACID; LESS SOL IN ALCOHOL; PRACTICALLY INSOL IN WATER;SOL IN CARBON TETRACHLORIDE;Solubility in water, mg/l at 25 °C: 0.09 (very poor);

Storage

2-8°C

Color Form

MONOCLINIC PLATELETS OR PRISMS FROM ETHER;WHITE CRYSTALLINE SOLID;

Complexity

202

Covalently-Bonded Unit Count

EC Number

238-154-8

Exact Mass

262.091g/mol

Heavy Atom Count

ICSC Number

0700

Monoisotopic Mass

262.091g/mol

NSC Number

215203

Odor

ODORLESS;

Other Experimental

TRIBOLUMINESCENT;

Rotatable Bond Count

RTECS Number

SZ3500000

Topological Polar Surface Area

0A^2

UNII

26D26OA393

UN Number

3077

Vapor Pressure

Vapor pressure, Pa at 50 °C: 0.017;

Application

Triphenylphosphine, polymer-bound, appears as white to yellow beads and serves multiple purposes in synthetic chemistry. This solid-supported reagent is particularly valuable for creating polymer-bound ylides, which are instrumental in Wittig reactions. It offers a superior alternative to traditional triphenylphosphine in the Mitsunobu reaction. Moreover, it facilitates the esterification of alkylphosphonic acids with primary alcohols by using iodine and imidazole. Additionally, it acts as a catalyst in the conversion of 3-[3-(1,3-dioxolan-2-yl)-1-hydroxypropyl]pyridine to 3-[1-bromo-3-(1,3-dioxolan-2-yl)propyl]pyridine with carbon tetrabromide and aids in the isomerization of (Z)-nitro olefins to (E)-isomers. This reagent is also effective in converting alcohols or carboxylic acids to their corresponding chlorides and, when combined with carbon tetrachloride, facilitates the coupling of N-alkoxycarbonyl α-amino acids and primary amines to form corresponding amides.

February 28, 2025

Efficient and Versatile Triphenylphosphine Resin

The polymer-bound triphenylphosphine from Alfa Chemistry is an impressive reagent. In our lab, it streamlined the Wittig reaction, enhancing product purity. Its application in Mitsunobu reactions also significantly improved yield consistency. Highly recommended for reliable research outcomes!