188837-56-1

Basic information

• Product Name: 1H-Indole-2-carboxylic acid, pentafluorophenyl ester
• CAS NO: 188837-56-1
• Molecular Formula: C15H6F5NO2
• Molecular Weight: 327.21
• Mol File: 188837-56-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1H-Indole-2-carboxylic acid, pentafluorophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylic acid, pentafluorophenyl ester(188837-56-1)
• EPA Substance Registry System: 1H-Indole-2-carboxylic acid, pentafluorophenyl ester(188837-56-1)

Safety Data

• Hazardous Substances Data: 188837-56-1(Hazardous Substances Data)

Upstream product

• 1477-50-5 Indole-2-carboxylic acid 
• 14533-84-7 pentafluorophenyl trifloroacetate 
• 771-61-9 2,3,4,5,6-pentafluorophenol 

Downstream Products

• 123500-70-9 (1H-indol-2-yl) (pyrrolidin-1-yl)methanone 
• 1155556-91-4 N-ethyl-N-phenyl-1H-indole-2-carboxamide 
• 1527472-61-2 N-benzyl-N-phenyl-1H-indole-2-carboxamide 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Transesterification of (hetero)aryl esters with phenols by an Earth-abundant metal catalyst

Readily available and inexpensive Earth-abundant alkali metal species are used as efficient catalysts for the transesterification of aryl or heteroaryl esters with phenols which is a challenging and underdeveloped transformation. The simple conditions and the use of heterogeneous alkali metal catalyst make this protocol very environmentally friendly and practical. This reaction fills in the missing part in transesterification reaction of phenols and provides an efficient approach to aryl esters, which are widely used in the synthetic and pharmaceutical industry.

Energy-efficient green catalysis: Supported gold nanoparticle-catalyzed aminolysis of esters with inert tertiary amines by C-O and C-N bond activations

Catalyzed by supported gold nanoparticles, an aminolysis reaction between various aryl esters and inert tertiary amines by C-O and C-N bond activations has been developed for the selective synthesis of tertiary amides. Comparison studies indicated that the gold nanoparticles could perform energy-efficient green catalysis at room temperature, whereas Pd(OAc)2 could not.

The effects of conformational constraints and steric bulk in the amino acid moiety of philanthotoxins on AMPAR antagonism

Philanthotoxin-343 (PhTX-343), a synthetic analogue of wasp toxin PhTX-433, is a noncompetitive antagonist at ionotropic receptors (e.g., AChR or iGluR). To determine possible effects of variations of the amino acid side chain, a library consisting of seventeen PhTX-343 analogues was prepared. Thus, tyrosine was replaced by either apolar, conformationally constrained, or bulky amino acids, whereas the acyl unit and the polyamine moiety were kept unchanged. Analogues with tertiary amide groups were prepared for the first time. Pentafluorophenyl esters were employed for amide bond formation, establishing general protocols for philanthotoxin solution- and solid-phase synthesis (39-90% and 42-54% overall yields, respectively). The analogues were tested for their ability to antagonize kainate-induced currents of 2-amino-3-(3-hydroxy-5-methyl- 4-isoxazoyl)propanoic acid receptors (AMPAR) expressed in Xenopus oocytes from rat brain mRNA. This showed that steric bulk in the amino acid moiety is well tolerated and suggests that binding to AMPAR does not involve the α-NHCO group as a donor in hydrogen bonding.