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Tri-3,5-xylylphosphine

Catalog Number
ACM69227470-2
Product Name
Tri-3,5-xylylphosphine
Structure
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CAS
69227-47-0
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Synonyms
Phosphine, tris(3,5-dimethylphenyl)-; Tris(3,5-dimethylphenyl)phosphine, 96%; AN-37902; CTK8C5349; MFCD03094579; TC-164724; ZINC59439992; 69227-47-0; FT-0655401; 227T470;
IUPAC Name
tris(3,5-dimethylphenyl)phosphane;
Molecular Weight
346.454g/mol
Molecular Formula
C24H27P;
Canonical SMILES
CC1=CC(=CC(=C1)P(C2=CC(=CC(=C2)C)C)C3=CC(=CC(=C3)C)C)C;
InChI
InChI=1S/C24H27P/c1-16-7-17(2)11-22(10-16)25(23-12-18(3)8-19(4)13-23)24-14-20(5)9-21(6)15-24/h7-15H,1-6H3;
InChI Key
XRALRSQLQXKXKP-UHFFFAOYSA-N;
Complexity
327
Covalently-Bonded Unit Count
1
Exact Mass
346.185g/mol
Heavy Atom Count
25
Monoisotopic Mass
346.185g/mol
Rotatable Bond Count
3
Topological Polar Surface Area
0A^2
Application
Tri-3,5-xylylphosphine serves as a versatile catalyst, primarily in the realm of organic synthesis. It is instrumental in advancing Cu/diphosphine-catalyzed asymmetric hydrogenation of heteroaromatic ketones and enones, and facilitates highly selective rhodium-catalyzed hydrogenation reactions. Its utility extends to the field of silicon-stereogenic silanaphthalenes, where it aids in both classical and kinetic resolution processes. Additionally, Tri-3,5-xylylphosphine plays a crucial role in the kinetic resolution of donor-functionalized secondary alcohols, achieved via Cu-H-catalyzed stereoselective silylation through dehydrogenative Si-O coupling with Si-stereogenic silanes. Furthermore, it is employed in comparative studies examining the conformational rigidity of silicon-stereogenic silanes within asymmetric catalysis.
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