(R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-[1,1'-binaphthalene]-2,2'-diol

Name: (R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-[1,1'-binaphthalene]-2,2'-diol
Brand: ChemScene
Availability: InStock
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CAS No. 215433-52-6
Cat. No. CS-0086958
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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(R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-[1,1'-binaphthalene]-2,2'-diol|CS-0086958

Structure of 215433-52-6

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General Information

CAS No. 215433-52-6
Cat. No. CS-0086958
Purity ≥98%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄₄H₃₀O₂
Molecular Weight 590.71
Synonym(s) (R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-1,1'-binaphthalene]-2,2'-diol
SMILES OC1=C(C2=C(C=CC=C3)C3=CC(C4=CC=C(C5=CC=CC=C5)C=C4)=C2O)C6=C(C=CC=C6)C=C1C7=CC=C(C8=CC=CC=C8)C=C7

Description

(R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-[1,1'-binaphthalene]-2,2'-diol features a rigid, chiral binaphthyl scaffold with two electron-rich biphenyl substituents that enhance π-stacking and metal coordination. This configuration delivers high enantioselectivity in asymmetric catalysis, particularly in transition-metal-catalyzed reactions where steric and electronic control are critical. Bench-stable and moisture-tolerant, it integrates seamlessly into synthetic workflows requiring robust chiral ligands.

Application

(R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-[1,1'-binaphthalene]-2,2'-diol serves as a chiral ligand scaffold in asymmetric catalysis, enabling enantioselective transformations through its rigid, C₂-symmetric binaphthyl core. The strategically positioned biphenyl substituents enhance steric differentiation and electronic tuning, while the diol functionality provides robust coordination to transition metals. This structure offers excellent bench stability, facilitates purification via chromatography, and supports broad functional group tolerance in palladium- and copper-catalyzed cross-coupling reactions.

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 : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 40.46
LogP 11.7392
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 5

Key Words

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(R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-[1,1'-binaphthalene]-2,2'-diol

CAS No. 215433-52-6

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