Lot numbers can be found on the outside label of a product:
N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(9R)-6'-methoxycinchonan-9-yl]thiourea
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CAS No. 852913-25-8
- Cat. No. CS-0091876
- Purity95%,Contains 15% Tetrahydrogen compound
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
![N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(9R)-6'-methoxycinchonan-9-yl]thiourea|CS-0091876](https://file.chemscene.com/productPIC/CS-0091876.gif)
Structure of 852913-25-8
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General Information
- CAS No. 852913-25-8
- Cat. No. CS-0091876
- Purity 95%,Contains 15% Tetrahydrogen compound
- MDL No. None
- Storage 4°C, protect from light, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₂₉H₂₈F₆N₄OS
- Molecular Weight 594.61
- Synonym(s) N-[3,5-Bis(Trifluoromethyl)Phenyl]-N-[(9R)-6-Methoxycinchonan-9-yl]- Thiourea
- SMILES S=C(NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)N[C@H](C2=C(C=C(OC)C=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)-6'-methoxycinchonan-9-yl]thiourea features a sterically hindered thiourea core paired with electron-deficient aryl and chiral quinoline moieties. This configuration enables strong hydrogen-bonding interactions and enantioselective recognition in asymmetric catalysis. The trifluoromethyl groups enhance lipophilicity and metabolic stability, while the methoxy-substituted cinchona scaffold provides a well-defined chiral environment. Designed for use in organocatalytic transformations, this compound delivers high enantiocontrol in reactions such as Michael additions and Mannich-type processes under standard conditions.
Application
N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(9R)-6'-methoxycinchonan-9-yl]thiourea serves as a chiral thiourea catalyst in asymmetric synthesis, enabling enantioselective transformations through dual hydrogen-bonding activation. Its rigid cinchona scaffold and electron-withdrawing trifluoromethyl aryl group enhance both catalytic activity and stereocontrol. The molecule exhibits bench stability, facilitates purification via crystallization, and demonstrates broad functional group tolerance in organocatalytic reactions such as Michael additions and Mannich-type processes.
Synthesis
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Route1
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287979-82-2 -
23165-29-9 - ~61%
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In-stock
852913-25-8
References
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Berkessel, Albrecht; Mukherjee, Santanu; Mueller, Thomas N.; Cleemann, Felix; Roland, Katrin; Brandenburg, Marc; Neudoerfl, Joerg-M.; Lex, Johann Organic and Biomolecular Chemistry, 2006 , vol. 4, # 23 p. 4319 - 4330
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Route2
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In-stock
56-54-2 - ~%
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In-stock
852913-25-8
References
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Asano, Keisuke; Matsubara, Seijiro Journal of the American Chemical Society, 2011 , vol. 133, # 42 p. 16711 - 16713
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Route3
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866140-03-6
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In-stock
852913-25-8
References
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Asano, Keisuke; Matsubara, Seijiro Journal of the American Chemical Society, 2011 , vol. 133, # 42 p. 16711 - 16713
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS06
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Signal Word : Danger
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UN#: 2811
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Class : 6.1
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Packing Group : Ⅲ
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Hazard Statements : H301
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 49.42
- LogP 7.2051
- H_Acceptors 4
- H_Donors 2
- Rotatable_Bonds 6
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Key Words
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