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Tris(4-chlorophenyl)phosphine
Catalog Number
ACM1159542
Product Name
Tris(4-chlorophenyl)phosphine
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/1159-54-2.gif)
CAS
1159-54-2
Synonyms
Tris(p-chlorophenyl)phosphine
IUPAC Name
tris(4-chlorophenyl)phosphane
Molecular Weight
365.62
Molecular Formula
C18H12Cl3P
Canonical SMILES
C1=CC(=CC=C1P(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)Cl;
InChI
IQKSLJOIKWOGIZ-UHFFFAOYSA-N
InChI Key
InChI=1S/C18H12Cl3P/c19-13-1-7-16(8-2-13)22(17-9-3-14(20)4-10-17)18-11-5-15(21)6-12-18/h1-12H
Boiling Point
427.6±40.0 °C(Predicted)
Melting Point
100-103 °C (lit.)
Purity
97%
Appearance
White solid
Complexity
275
Covalently-Bonded Unit Count
1
EC Number
214-596-7
Exact Mass
363.974g/mol
Heavy Atom Count
22
Isomeric SMILES
C1=CC(=CC=C1P(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)Cl
Monoisotopic Mass
363.974g/mol
NSC Number
136459
Rotatable Bond Count
3
Topological Polar Surface Area
0A^2
Application
Tris(4-chlorophenyl)phosphine serves as a versatile catalyst and cocatalyst, presented as a white to light yellow crystalline powder. It is employed in the preparation of chromans and (E,E)-1,3-dienes through the reaction of γ-substituted allenoates with aldehydes and facilitates solvent-free Heck reactions. Additionally, it acts as a cocatalyst in several advanced chemical processes, including the regioselective carbomagnesiation of terminal alkynes and enynes using alkyl Grignard reagents, rhodium-catalyzed coordination-assisted regioselective alkenylation of aromatic C-H bonds with terminal silylacetylenes, rhodium-catalyzed hydrogenation reactions, and platinum-catalyzed allylation reactions.
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