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trans-1,2-Bis(diphenylphosphino)ethylene

Catalog Number
ACM983813-1
Product Name
trans-1,2-Bis(diphenylphosphino)ethylene
Structure
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CAS
983-81-3
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Synonyms
(Z)-1,2-Bis(diphenylphosphino)ethene; TR-031825; A845854; SCHEMBL338473; [(z)-ethene-1,2-diyl]bis(diphenylphosphine); NSC 132587; SCHEMBL338475; NCKJIJSEWKIXAT-QURGRASLSA-N; DB-009847; cis-1,2-bis(diphenylphosphino)ethylene, min. 98%;
IUPAC Name
[(E)-2-diphenylphosphanylethenyl]-diphenylphosphane;
Molecular Weight
396.41g/mol
Molecular Formula
C26H22P2;
Canonical SMILES
C1=CC=C(C=C1)P(C=CP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4;
InChI
InChI=1S/C26H22P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-22H/b22-21+;
InChI Key
NCKJIJSEWKIXAT-QURGRASLSA-N;
Complexity
371
Covalently-Bonded Unit Count
1
Defined Bond Stereocenter Count
1
EC Number
213-570-2
Exact Mass
396.12g/mol
Heavy Atom Count
28
Monoisotopic Mass
396.12g/mol
Rotatable Bond Count
6
Topological Polar Surface Area
0A^2
Application
Trans-1,2-Bis(diphenylphosphino)ethylene, a white to light yellow crystalline powder, serves a vital role in various catalytic and synthetic applications. It acts as a catalyst in the coupling of primary and secondary alkyl halides with aryl Grignard reagents and facilitates the homogeneous hydrogenation of carbon dioxide mediated by ruthenium. Additionally, this compound is used as a reactant in the preparation of cyclopalladated derivatives of benzylidene and the synthesis of cyclopalladated complexes containing tridentate thiosemicarbazone ligands, which have significance as antimalarial agents. Furthermore, it plays a crucial part in the catalytic asymmetric intramolecular hydroamination of alkynylamines, demonstrating its versatility and importance in advanced chemical processes.
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