4-Iodo-2-methyl-1-(2,2,2-trifluoroethyl)-1H-imidazole

Name: 4-Iodo-2-methyl-1-(2,2,2-trifluoroethyl)-1H-imidazole
Brand: ChemScene
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CAS No. 824431-97-2
Cat. No. CS-0376963
Molecule weight290.02
Purity≥97%
MDL No.MFCD27929281

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4-Iodo-2-methyl-1-(2,2,2-trifluoroethyl)-1H-imidazole|CS-0376963

Structure of 824431-97-2

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General Information

CAS No. 824431-97-2
Cat. No. CS-0376963
Purity ≥97%
MDL No. MFCD27929281
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₆F₃IN₂
Molecular Weight 290.02
Synonym(s) 1H-Imidazole,4-iodo-2-methyl-1-(2,2,2-trifluoroethyl)
SMILES FC(F)(F)CN1C=C(I)N=C1C

Description

4-Iodo-2-methyl-1-(2,2,2-trifluoroethyl)-1H-imidazole features a sterically accessible imidazole core functionalized with a trifluoroethyl group and an iodine substituent at the 4-position. This combination delivers enhanced stability and tailored electronic properties, enabling efficient coupling in cross-coupling reactions. The molecule exhibits favorable solubility in common organic solvents and maintains integrity under standard bench conditions.

Application

4-Iodo-2-methyl-1-(2,2,2-trifluoroethyl)-1H-imidazole serves as a versatile building block for constructing bioactive imidazole scaffolds in medicinal chemistry. The iodo group enables efficient palladium-catalyzed cross-coupling reactions, while the trifluoromethyl ether functionality enhances metabolic stability and modulates lipophilicity. This compound exhibits excellent bench stability, facilitates straightforward purification, and demonstrates broad functional group tolerance in standard coupling protocols.

Synthesis

Route1
- In-stock
  
  433-06-7
- In-stock
  
  73746-45-9
- ~43%
- In-stock
  
  824431-97-2
References
- Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael Patent: US2011/230462 A1, 2011 ; Location in patent: Page/Page column 110 ; US 20110230462 A1

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 17.82
LogP 2.35842
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Key Words

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4-Iodo-2-methyl-1-(2,2,2-trifluoroethyl)-1H-imidazole

CAS No. 824431-97-2

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