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CS-W001157 4
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1,3-Bis((R)-1-(naphthalen-1-yl)ethyl)-1H-imidazol-3-ium chloride

  • CAS No. 186354-48-3

  • Cat. No. CS-0521140
  • Purity≥95%
  • MDL No.None
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    If shipping is charged to your FedEx account, the HazMat fee will be billed directly by the courier. Otherwise, the fee will be included on your invoice. To help you avoid the HazMat fee, we can package a 5g order of a class 6.1 packing group I or II material as five separate 1g units, and a 100g order of any other dangerous good as four 25g units. This packaging adjustment will be made unless you instruct otherwise on your purchase order. Below, you will find the fee schedule from FedEx for handling hazardous materials.

    Type
    HazMat Fee
    Excepted Quantity $0.00
    FedEx Limited Quantities Ground $0.00
    Hazmat Ground shipping $50.00+
    Inaccessible (Haz class 6.1 or 9), Domestic $68.00+
    Accessible (Haz class 3, 4, 5 or 8), Domestic $158.00+
    Inaccessible (Haz class 6.1 or 9), International $108.00+
    Accessible (Haz class 3, 4, 5 or 8), International $238.00+

    An item is classified as a dangerous good if our website displays Hazardous Material (HazMat) information for it.

    There is a HazMat shipping fee for each item that qualifies as a dangerous good. Please contact our quotation team via email to confirm the details.

*For research and further manufacturing use only, not for direct human use.

1,3-Bis((R)-1-(naphthalen-1-yl)ethyl)-1H-imidazol-3-ium chloride|CS-0521140

Structure of 186354-48-3

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Description

This chiral imidazolium salt features two (R)-1-(naphthalen-1-yl)ethyl groups flanking the imidazolium core, delivering enhanced stereochemical control and rigidity. The chloride counterion ensures good solubility in polar solvents while maintaining stability under standard handling conditions. This structure enables efficient asymmetric catalysis and serves as a robust ligand scaffold in transition-metal complexes.

Application

1,3-Bis((R)-1-(naphthalen-1-yl)ethyl)-1H-imidazol-3-ium chloride serves as a chiral, bench-stable N-heterocyclic carbene precursor with enhanced steric bulk from the naphthyl-substituted alkyl groups. It facilitates asymmetric catalysis in palladium- and copper-mediated cross-coupling reactions, offering improved enantioselectivity and functional group tolerance. The chloride counterion supports solubility and ease of handling, making it suitable for scalable synthesis and process development.

General Information

  • CAS No. 186354-48-3
  • Cat. No. CS-0521140
  • Purity ≥95%
  • MDL No. None
  • Storage RT, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₇H₂₅ClN₂
  • Molecular Weight 412.95
  • Synonym(s) 1,3-Bis((R)-1-(naphthalen-1-yl)ethyl)-1H imidazol-3-ium chlorid
  • SMILES C[C@@H]([N+]1=CN([C@@H](C2=C3C=CC=CC3=CC=C2)C)C=C1)C4=C5C=CC=CC5=CC=C4.[Cl-]

Computational Chemistry Data

  • TPSA   8.81
  • LogP   3.3046
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   4

Safety Information

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GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group :
Hazard Statements : H302-H314
Precautionary Statements : P260-P264-P270-P280-P301+P330+P331-P304+P340-P330-P363-P405-P501

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