184775-08-4

Basic information

• Product Name: benzyl 4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate
• Synonyms: benzyl 4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate
• CAS NO: 184775-08-4
• Molecular Weight: 327.303
• Mol File: 184775-08-4.mol

Chemical Properties

• CAS DataBase Reference: benzyl 4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate(184775-08-4)
• EPA Substance Registry System: benzyl 4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate(184775-08-4)

Safety Data

• Hazardous Substances Data: 184775-08-4(Hazardous Substances Data)

Upstream product

• 40236-19-9 benzyl 3,5-dimethylpyrrole-2-carboxylate 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 

Downstream Products

• 205492-38-2 benzyl 3,5-dimethyl-4-(trifluoroacetyl)pyrrole-2-carboxylate 
• 205492-41-7 benzyl 3,5-dimethyl-4-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate 
• 205492-40-6 benzyl (S)-4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate 
• 220802-60-8 benzyl 4-methyl-3-((S)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate 
• 220802-59-5 benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate 
• 220802-47-1 benzyl 4-((S)-1-acetoxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate 
• 220802-46-0 benzyl 4-((R)-1-acetoxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate 
• 220802-52-8 benzyl 4-((S)-1-acetoxy-2,2,2-trifluoroethyl)-5-methoxycarbonyl-3-methylpyrrole-2-carboxylate 
• 220802-51-7 benzyl 4-((R)-1-acetoxy-2,2,2-trifluoroethyl)-5-methoxycarbonyl-3-methylpyrrole-2-carboxylate 
• 380231-99-2 benzyl 5-acetoxymethyl-3-methyl-4-((S)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate 
• 380231-94-7 benzyl 5-acetoxymethyl-3-methyl-4-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate 
• 220802-50-6 3-(1-acetoxy-2,2,2-trifluoro-ethyl)-4-methyl-1H-pyrrole-2,5-dicarboxylic acid 5-benzyl ester 
• 220802-49-3 3-(1-acetoxy-2,2,2-trifluoro-ethyl)-4-methyl-1H-pyrrole-2,5-dicarboxylic acid 5-benzyl ester 
• 220802-66-4 dibenzyl (3R,4'S)-4,3'-dimethyl-3,4'-bis(2,2,2-trifluoro-1-hydroxyethyl)-2,2'-dipyrrylmethane-5,5'-dicarboxylate 

Relevant articles and documents

Syntheses of chiral fluorine analogs of hematoporphyrin

Four chiral fluorine analogs of hematoporphyrin, (R,R)-, (R,S)-, (S,R)-, and (S,S)-3,8-bis(2,2,2-trifluoro-1-hydroxyethyl)deuteroporphyrins, were synthesized starting from pyrroles with a chiral 2,2,2-trifluoro-1-hydroxyethyl (TFHE) group. This chiral TFHE group was obtained by asymmetric reduction of a trifluoroacetyl group. Among these chiral analogs of hematoporphyrin, the (S,S)-isomer showed higher affinity for cancer cells than other stereoisomers.

Synthesis of a fluorine analog of hematoporphyrin by ring closure

Benzyl 3,5-dimethyl-2-pyrrolecarboxylate (1) was converted to 4-(2,2,2-trifluoro-1-hydroxyethyl) derivative (2) on treatment with trifluoro-acetaldehyde ethyl hemiacetal in the presence of zinc chloride. After protection of the hydroxy group, 2 was converted to benzyl 4-methyl-3-(2,2,2-trifluoro-1-methoxyethyl)2-pyrrolecarboxylate (9) and benzyl 5-acetoxymethyl-3-methyl-4-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolecarboxylate (10). Both esters were condensed to a dipyrrolomethane compound (11), which was debenzylated, decarboxylated, and condensed with a bottom half of the porphyrin to give a hexafluorohematoporphyrin derivative (14), potentially useful for photodynamic therapy of cancer.

Synthesis of a fluorine analog of hematoporphyrin by ring closure

Benzyl 3,5-dimethyl-2-pyrrolecarboxylate (1) was converted to 4-(2,2,2-trifluoro-1-hydroxyethyl) derivative (2) on treatment with trifluoroacetaldehyde ethyl hemiacetal in the presence of zinc chloride. After protection of the hydroxyl group with a methyl group, 2 was converted to benzyl 4-methyl-3-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolecarboxylate (9) and benzyl 5-acetoxymethyl-3-methyl-4-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolec arboxylate (10). Both esters were condensed to dipyrylmethane compound 11, which was debenzylated, decarboxylated, and condensed with a bottom half of the porphyrin to give hexafluorohematoporphyrin derivative 14, potentially useful for photodynamic therapy of cancer.