N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(R)-2'-(dimethylamino)[1,1'-binaphthalen]-2-yl]thiourea

Name: N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(R)-2'-(dimethylamino)[1,1'-binaphthalen]-2-yl]thiourea
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CAS No. 866940-63-8
Cat. No. CS-0091915
Purity≥95%
MDL No.MFCD27920533

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N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(R)-2'-(dimethylamino)[1,1'-binaphthalen]-2-yl]thiourea|CS-0091915

Structure of 866940-63-8

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General Information

CAS No. 866940-63-8
Cat. No. CS-0091915
Purity ≥95%
MDL No. MFCD27920533
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₁H₂₃F₆N₃S
Molecular Weight 583.59
Synonym(s) N-[3,5-bis(trifluoromethyl)phenyl]-N'-[(1R)-2'-(dimethylamino)[1,1'-binaphthalen]-2-yl]- Thiourea
SMILES S=C(NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)NC2=C(C3=C(C=CC=C4)C4=CC=C3N(C)C)C5=CC=CC=C5C=C2

Description

This thiourea features a chiral binaphthyl moiety paired with electron-deficient trifluoromethyl aryl groups, enabling strong hydrogen-bonding interactions in asymmetric catalysis. The (R)-configured binaphthyl unit imparts high enantioselectivity, while the trifluoromethyl substituents enhance both stability and binding affinity.

Application

N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(R)-2'-(dimethylamino)[1,1'-binaphthalen]-2-yl]thiourea serves as a chiral, sterically hindered thiourea catalyst that enables enantioselective transformations in asymmetric synthesis. Its trifluoromethylated aryl group enhances electron-withdrawing character and solubility, while the binaphthyl scaffold provides robust chirality transfer. The dimethylamino substituent fine-tunes hydrogen-bonding basicity, facilitating substrate activation in organocatalytic reactions. This compound demonstrates bench stability and compatibility with standard purification methods, making it suitable for iterative optimization in catalytic asymmetric processes.

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 : H413
Precautionary Statements : P264-P270-P330

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Computational Chemistry Data

TPSA 27.3
LogP 9.5725
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 4

Key Words

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N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(R)-2'-(dimethylamino)[1,1'-binaphthalen]-2-yl]thiourea

CAS No. 866940-63-8

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