Cyclopropyl trifluoromethanesulfonate

Name: Cyclopropyl trifluoromethanesulfonate
Brand: ChemScene
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CAS No. 25354-42-1
Cat. No. CS-0169340
Purity≥95%
MDL No.None

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Cyclopropyl trifluoromethanesulfonate|CS-0169340

Structure of 25354-42-1

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General Information

CAS No. 25354-42-1
Cat. No. CS-0169340
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₅F₃O₃S
Molecular Weight 190.14
Synonym(s) Methanesulfonic acid, trifluoro-, cyclopropyl ester
SMILES O=S(C(F)(F)F)(OC1CC1)=O

Description

Cyclopropyl trifluoromethanesulfonate serves as a highly reactive triflate ester for cyclopropyl transfer in cross-coupling and functionalization reactions. The strained cyclopropyl ring enhances electrophilicity, while the trifluoromethylsulfonyl group ensures excellent leaving group ability. This combination enables efficient C–C bond formation under mild conditions.

Application

Cyclopropyl trifluoromethanesulfonate serves as a highly reactive cyclopropyl transfer agent in transition-metal-catalyzed cross-coupling reactions. Its triflate leaving group enables efficient C–C bond formation under mild conditions, facilitating the direct introduction of cyclopropyl motifs into complex molecular architectures. The stability of the cyclopropyl ring and the robustness of the triflate functionality make this reagent particularly valuable for constructing bioactive scaffolds and natural product analogs with high functional group tolerance and predictable stereochemical outcomes.

Synthesis

Route1
- 358-23-6
- 16545-68-9
- ~53%
- In-stock
  
  25354-42-1
References
- Banert, Klaus Chemische Berichte, 1985 , vol. 118, # 4 p. 1564 - 1574

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS02,GHS05,GHS07
Signal Word : Danger	UN#: 2924
Class : 3,8	Packing Group : Ⅲ
Hazard Statements : H225-H302-H314
Precautionary Statements : P210-P233-P240-P241-P242-P243-P260-P264-P270-P280-P301+P330+P331-P304+P340-P330-P363-P370+P378-P405-P501

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Computational Chemistry Data

TPSA 43.37
LogP 1.015
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Sulfonate

Building Blocks Skeleton Fatty ring compounds Cyclopropane compounds

Key Words

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Cyclopropyl trifluoromethanesulfonate

CAS No. 25354-42-1

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