N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-ylthiourea

Name: N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-ylthiourea
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CAS No. 851477-19-5
Cat. No. CS-0091864
Purity≥97%
MDL No.MFCD23704929

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-ylthiourea|CS-0091864

Structure of 851477-19-5

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General Information

CAS No. 851477-19-5
Cat. No. CS-0091864
Purity ≥97%
MDL No. MFCD23704929
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₈H₂₆F₆N₄S
Molecular Weight 564.59
Synonym(s) None
SMILES S=C(NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)N[C@H](C2=C(C=CC=C3)C3=NC=C2)[C@]4(C[C@@H]5CC[N@]4C[C@@H]5C=C)[H]

Description

N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-ylthiourea features a chiral cinchona scaffold paired with electron-deficient aryl thiourea functionality, enabling precise asymmetric catalysis. The trifluoromethyl groups enhance lipophilicity and stabilize transition states in enantioselective transformations. This bifunctional architecture supports efficient hydrogen-bonding networks and delivers high enantiomeric excesses in metal-free organocatalytic reactions under standard conditions.

Application

N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-ylthiourea serves as a chiral bifunctional catalyst in asymmetric synthesis, leveraging the rigid cinchona alkaloid scaffold for stereocontrol. The thiourea moiety engages in hydrogen bonding with substrates, while the electron-deficient aryl group enhances electrophile activation. Its bench-stable nature and compatibility with common solvents facilitate reliable operation in enantioselective transformations, particularly in Michael additions and Mannich 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 : H413
Precautionary Statements : P264-P270-P330

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Computational Chemistry Data

TPSA 40.19
LogP 7.1965
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 5

Key Words

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N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-ylthiourea

CAS No. 851477-19-5

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