[(R)-2′-(Diphenylphosphino)[1,1′-binaphthalen]-2-yl]diphenylphosphine oxide

Name: [(R)-2′-(Diphenylphosphino)[1,1′-binaphthalen]-2-yl]diphenylphosphine oxide
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CAS No. 152646-80-5
Cat. No. CS-0512724
Purity≥95%
MDL No.None

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[(R)-2′-(Diphenylphosphino)[1,1′-binaphthalen]-2-yl]diphenylphosphine oxide|CS-0512724

Structure of 152646-80-5

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General Information

CAS No. 152646-80-5
Cat. No. CS-0512724
Purity ≥95%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄₄H₃₂OP₂
Molecular Weight 638.67
Synonym(s) None
SMILES O=P(C1=CC=CC=C1)(C2=CC=C3C=CC=CC3=[C@]2[C@@]4=C5C=CC=CC5=CC=C4P(C6=CC=CC=C6)C7=CC=CC=C7)C8=CC=CC=C8

Description

This chiral phosphine oxide features a binaphthyl backbone with a diphenylphosphino group and a phosphoryl oxygen, enabling robust coordination in asymmetric catalysis. The stereochemistry at the 2′-position ensures high enantioselectivity in transition metal complexes. Bench-stable and moisture-tolerant, it integrates seamlessly into palladium-catalyzed cross-coupling systems.

Application

[(R)-2′-(Diphenylphosphino)[1,1′-binaphthalen]-2-yl]diphenylphosphine oxide serves as a chiral ligand in transition metal-catalyzed asymmetric synthesis, particularly in palladium- and nickel-mediated cross-coupling reactions. Its rigid binaphthyl backbone and phosphine oxide functionality enhance stereocontrol and catalyst stability. The molecule exhibits excellent bench stability, facilitates efficient purification, and demonstrates broad functional group tolerance in standard synthetic workflows.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

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Computational Chemistry Data

TPSA 17.07
LogP 9.0576
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 7

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

152646-80-5 sigma152646-80-5 manufacturer152646-80-5 price152646-80-5 structure152646-80-5 SDSbuy 152646-80-5152646-80-5 supplier152646-80-5 uses152646-80-5 molecular weightprice of 152646-80-5152646-80-5 chemical name formula of 152646-80-5

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[(R)-2′-(Diphenylphosphino)[1,1′-binaphthalen]-2-yl]diphenylphosphine oxide

CAS No. 152646-80-5

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