150097-92-0

Basic information

• Product Name: METHYL 5-PENTAFLUOROETHYL-2-PROPYLIMIDAZOLE-4-CARBOXYLATE
• Synonyms: METHYL 5-PENTAFLUOROETHYL-2-PROPYLIMIDAZOLE-4-CARBOXYLATE
• CAS NO: 150097-92-0
• Molecular Formula: C₁₀H₁₁F₅N₂O₂
• Molecular Weight: 286.2
• Mol File: 150097-92-0.mol

Chemical Properties

• Boiling Point: 354.5±42.0 °C(Predicted)
• Appearance: /
• Density: 1.368±0.06 g/cm3(Predicted)
• PKA: 8.38±0.10(Predicted)
• CAS DataBase Reference: METHYL 5-PENTAFLUOROETHYL-2-PROPYLIMIDAZOLE-4-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-PENTAFLUOROETHYL-2-PROPYLIMIDAZOLE-4-CARBOXYLATE(150097-92-0)
• EPA Substance Registry System: METHYL 5-PENTAFLUOROETHYL-2-PROPYLIMIDAZOLE-4-CARBOXYLATE(150097-92-0)

Safety Data

• Hazardous Substances Data: 150097-92-0(Hazardous Substances Data)

Upstream product

• 354-64-3 Pentafluoroethyl iodide 
• 150097-91-9 Methyl 2-propyl-4⁽⁵⁾-iodoimidazole-5⁽⁴⁾-carboxylate 
• 104721-32-6 methyl 4,4,5,5,5-pentafluoropent-2-ynoate 
• 68282-39-3 2-Propyl-4⁽⁵⁾-(hydroxymethyl)imidazole 
• 134380-65-7 2-Propyl-4⁽⁵⁾-cyano-5⁽⁴⁾-iodoimidazole 
• 134051-70-0 2-Propyl-4⁽⁵⁾-Iodoimidazole-5⁽⁴⁾-carboxaldehyde 
• 134051-69-7 2-Propyl-4⁽⁵⁾-(hydroxymethyl)-5⁽⁴⁾-iodoimidazole 

Downstream Products

• 150097-93-1 Methyl 4-(pentafluoroethyl)-2-propyl-1-<<2'-biphenyl-4-yl>methyl>imidazole-5-carboxylate 

Relevant articles and documents

Efficient Synthesis of Fluoroalkylated Imidazoles via a Metal-Free Cascade Michael Addition/Azidation/Cycloamination Process

In the presence of KI and (diacetoxyiodo)benzene (PIDA), primary amines bearing an α-hydrogen can be efficiently converted to fluoroalkylated imidazoles by reacting with fluoroalkylated alkynes and sodium azide via a cascade Michael addition/azidation/cycloamination process. KI plays a crucial role in this reaction by generating iodine(I) species to promote the cyclization. Substrate scope was explored, and the application of this protocol was demonstrated. Additionally, a plausible reaction mechanism was proposed.

Practical Synthesis and Regioselective Alkylation of Methyl 4(5)-(Pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate To Give DuP 532, a Potent Angiotensin II Antagonist

DuP 532 (2), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes.One route, which is more practical for large-scale synthesis, required the preparation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (9).This imidazole was synthesized in five steps from commercially available 11 in 32percent overall yield.Alternate perfluoroalkylation methods of the iodoimidazole precursor 14 are presented.Imidazole 9 is remarkably stable to basic conditions and is alkylated by 2--4'-(bromomethyl) -1,1'-biphenyl (8), giving only the desired regioisomer.A comparison of the alkylation of the trisubstituted precursors and analogues to 9 with 8 indicate that even under mildly basic conditions (K2CO3/DMF), the mechanism is SE2cB (anionic), except for 2-propyl-4(5)-(hydroxymethyl)imidazole (11) which alkylates as a neutral species (SE2')