N,N'-(S)-[1,1'-Binaphthalene]-2,2'-diylbis[N'-[3,5-bis(trifluoromethyl)phenyl]thiourea]

Name: N,N'-(S)-[1,1'-Binaphthalene]-2,2'-diylbis[N'-[3,5-bis(trifluoromethyl)phenyl]thiourea]
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CAS No. 914497-25-9
Cat. No. CS-0092679
Molecule weight826.72
Purity≥97%
MDL No.MFCD31707565

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N,N'-(S)-[1,1'-Binaphthalene]-2,2'-diylbis[N'-[3,5-bis(trifluoromethyl)phenyl]thiourea]|CS-0092679

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General Information

CAS No. 914497-25-9
Cat. No. CS-0092679
Purity ≥97%
MDL No. MFCD31707565
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₈H₂₂F₁₂N₄S₂
Molecular Weight 826.72
Synonym(s) N,N'-(S)-[1,1'-Binaphthalene]-2,2'-diylbis[N'-[3,5-bis(trifluoromethyl)phenyl]thiourea
SMILES S=C(NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)NC2=[C@]([C@]3=C(C=CC=C4)C4=CC=C3NC(NC5=CC(C(F)(F)F)=CC(C(F)(F)F)=C5)=S)C6=CC=CC=C6C=C2

Description

This chiral thiourea features a binaphthyl backbone paired with electron-deficient trifluoromethyl-substituted aryl groups, enabling strong hydrogen-bonding interactions. The scaffold delivers high enantioselectivity in asymmetric catalysis and exhibits excellent stability under standard bench conditions.

Application

N,N'-(S)-[1,1'-Binaphthalene]-2,2'-diylbis[N'-[3,5-bis(trifluoromethyl)phenyl]thiourea] serves as a chiral bifunctional ligand in asymmetric catalysis, leveraging its rigid binaphthyl backbone and electron-deficient thiourea groups to enable enantioselective transformations. The trifluoromethyl-substituted aryl moieties enhance both stability and hydrogen-bonding capacity, facilitating effective activation of substrates in reactions such as Michael additions and Mannich-type cyclizations. Its bench-stable crystalline nature simplifies handling and purification, making it suitable for scalable synthesis applications.

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-P302+P352

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Computational Chemistry Data

TPSA 48.12
LogP 13.353
H_Acceptors 2
H_Donors 4
Rotatable_Bonds 5

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N,N'-(S)-[1,1'-Binaphthalene]-2,2'-diylbis[N'-[3,5-bis(trifluoromethyl)phenyl]thiourea]

CAS No. 914497-25-9

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